IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS

THIS INVENTION relates to compounds and compositions having activity against the enzyme HIV-1 reverse transcriptase.

Highly active antiretroviral treatment (HAART) is a treatment regimen for HIV-AIDS sufferers which combines a cocktail of antiretroviral drugs chosen from a number of different classes. One of these classes comprises the non-nucleoside reverse transcriptase inhibitors (NNRTIs). These drugs act by inhibiting the enzyme HIV-1 reverse transcriptase. This enzyme is a validated target for the development of anti-HIV drugs. There are a number of NNRTIs that are FDA approved and one of these drugs generally forms part of the first-line treatment regimen against HIV-AIDS. There are a number of advantages associated with this class. One of the advantages is the excellent selectivity index (ratio of 50% cytotoxic concentration to 50% antivirally effective concentration) displayed by these drugs, which is usually of the order of 10,000-100,000. This high selectivity makes the NNRTI class the least toxic of the clinically approved antiretrovirals and makes these drugs suitable for use in the prevention of mother to child transmission. The reason for the high selectivity is the fact that NNRTIs only recognise and bind to HIV-1 reverse transcriptase, not to any other RTs or DNA or RNA polymerases. These drugs act by binding to a lipophilic, non-substrate binding pocket located about 10 Å from the substrate binding site. This binding results in conformational changes within the reverse transcriptase catalytic site that leads to a dramatic slowing down of the catalytic activity. The allosteric inhibitors of reverse transcriptase (RT) possess very different structural characteristics and as many as 50 diverse structural classes have been found to have activity against reverse transcriptase. The first generation of NNRTIs (exemplified by nevirapine and delavirdine) is sensitive to the development of drug resistance and even a single amino acid mutation in the NNRTI binding region of RT confers a high level of drug resistance. There is accordingly a requirement for NNRTIs which can inhibit as many different RT mutants as possible.

The applicant is aware of PCT/US2008/082531 entitled “Non-nucleoside reverse transcriptase inhibitors” (filed on 5 Nov. 2008) which claims the priority of U.S. Ser. No. 60/986,990 (filed on 9 Nov. 2007). The generic structure disclosed in this document covers a very large number of compounds. The document specifically discloses about 11600 compounds. However, inhibition data are provided for only about 30 compounds. The generic disclosure of the present application covers a substantially smaller number of compounds and those compounds of PCT/US2008/082531 which fall within the scope of the generic structure of the present application have been excluded by the introduction of provisos.

According to a first aspect of the invention there is provided a compound selected from compounds of the formula A or B

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in which, for formula A,

- R is selected from alkyl, branched alkyl, cycloalkyl, aryl, substituted aryl, naphthyl, benzyl, adamantyl and polycycloalkyl,
  - R¹is selected from alkyl, cycloalkyl, substituted alkyl, branched alkyl, phenyl, substituted phenyl, substituted benzyl, heteroaryl, substituted heteroaryl, oxacycloalkyl, bicycloalkyl, furyl, substituted furyl, thienyl and substituted thienyl, isoxazolyl, substituted isoxazolyl
  - R²-R⁵are independently selected from H, halogen, cyano, alkoxy, aryloxy, substituted aryl, alkyl and substituted alkyl, or R²and R³together form a carbocyclic ring or, independently, R⁴and R⁵together form a carbocyclic ring,
  - R⁶is H, alkyl or alkanoyl, provided that
  - (a) if R is cyclohexyl and R²-R⁶are H, then R¹is not 2-bromophenyl, 3-bromophenyl, 2-chlorophenyl, 3-chlorophenyl, 2-trifluoromethylphenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 4-fluorophenyl, isopropyl, 2-furyl, 2-hydroxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl or 2-fluorophenyl;
  - (b) if R is cyclopentyl and R²-R⁶are H, then R¹is not 2-bromophenyl, 3-bromophenyl, 2-chlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 2,4-difluorophenyl, 2-trifluoromethylphenyl or 2-fluorophenyl;
  - (c) if R is cyclohexyl or cyclopentyl and R³, R⁴, R⁵and R⁶are H, and R²is methyl, then R¹is not 2-chlorophenyl;
  - (d) if R is cyclohexyl or cyclopentyl and R², R⁴, R⁵and R⁶are H, and R³is methyl then R¹is not 2-chlorophenyl;
  - (e) if R is cyclohexyl or cyclopentyl and R², R³, R⁵and R⁶are H, and R⁴is methyl then R¹is not 2-chlorophenyl;
  - (f) if R is cyclohexyl or cyclopentyl, and R², R³, R⁴and R⁶are H, and R⁵is methyl, ethyl or trifluoromethyl, then R¹is not 2-chlorophenyl, 2-fluorophenyl, 2,6-difluorophenyl, 2-fluoro-5-methylphenyl, 2-fluoro-6-methoxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,4-difluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-pyridinyl, 2-fluoro-4-pyridinyl or 2-chloro-6-fluorophenyl;
  - (g) if R is cyclohexyl, and R², R³and R⁵are H, and R⁴is fluorine, chlorine or bromine, then R¹is not 2-chlorophenyl;
  - (h) if R is cyclohexyl, and R³and R⁵are methyl and R², R⁴and R⁶are H R¹is not 2-chlorophenyl;
  - and in which, for formula B,

R is cycloalkyl and R¹is substituted aryl.

The alkyl and branched alkyl groups of R¹may be optionally substituted by one or more heteroatoms. The heteroatoms may be oxygen, nitrogen or sulphur. For example the alkyl group may be substituted by a thiomethyl group. The substituted alkyl group may, therefore, be a 2-thiomethylethyl group. The phenyl group may optionally be substituted by one or more substituents selected from halogen, OH, alkyl, alkoxy, cyano, amino, substituted alkyl, halo or nitro. The heteroaryl group may be an O, N or S heteroaryl group and may, for example, be selected from oxazolyl, isoxazolyl, substituted isoxazolyl, furanyl, and thiophenyl groups.

The halogen may be selected from one or more of F, Cl and Br.

The cycloalkyl group may be selected from C₃-C₆cycloalkyl groups and adamantane. For example, the cycloalkyl group may be a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or tetrahydrofuranyl group.

The alkyl and branched alkyl groups may be selected from C₂to C₁₂alkyl and branched alkyl groups. Preferred alkyl and branched alkyl groups include 2-pentyl, 1-butyl, 2-propyl, 2-butyl and 1-pentyl and 1-octyl.

Examples of preferred compounds of the invention, of formula A are compounds in which:

(a) R is selected from ethyl, 2-morpholinoethyl, 1-butyl, 2-pentyl, 1-pentyl, 1,1,3,3-tetramethylbutyl, isopropyl, cyclohexyl, cyclopropyl, 4-(3,4-dichlorophenoxy)butyl, 1-adamantyl, 4-methoxyphenyl, 2-naphthyl, benzyl, 4-chlorobenzyl, 2-chloro-6-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, cyclopentyl;

(b) R¹is selected from ethyl, 2-(methylthio)ethyl, 1-propyl, 2-butyl, 2-methyl-1-propyl, 2,2-dimethyl-1-propyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-pentyl, 2-pentyl, 3-pentyl, tert-butyl, isopropyl, isobutyl, 1-octyl, 1-phenylethyl, 2-hydroxyphenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-nitrophenyl, 2-fluorophenyl, 4-fluorophenyl, 3-ethoxy-4-hydroxy-phenyl, 4-dimethylaminophenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxy-4-hydroxyphenyl, 4-benzyloxyphenyl, 2,4-dimethoxyphenyl, 4-hydroxy-3-methoxy-phenyl, 3-hydroxy-4-methoxy-phenyl, 2,3,6-trichlorophenyl, 2-fluoro-(3-methoxy)phenyl, 3-chloro-2-fluoro-phenyl, 2-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 4-chloro-3-fluoro-phenyl, 2-chloro-6-fluoro-5-methyl-phenyl, 3-(5-methyl)isoxazolyl, 2-(5-hydroxymethyl)furanyl, 2-furanyl, 2-(5-chloro)furanyl, 2-(5-ethyl)thienyl, 2-(3-methyl)thienyl, 2,4,5-trifluorophenyl, 3-(2,5-dimethoxy)tetrahydrofuranyl, 4-cyanophenyl, 3-cyanophenyl, norpinenyl;

(d) R³is selected from H, methyl, chloro;

(e) R⁴is selected from H, chloro, fluoro, methyl, bromo, nitrile, 2-methylphenyl, 4-methoxyphenyl,

(f) R⁵is selected from H, methyl, chloro, bromo, 2-methylphenyl, phenyloxy, 4-methoxyphenyl, ethoxy, cyano;

(g) R⁶is selected from H, ethyl, acetyl,

(h) R⁴and R⁵together form an aromatic ring.

(i) R²and R³together form an aromatic ring.

According to a second aspect of the invention there is provided a composition for use in treating a subject who has been infected with HIV, the composition including a compound selected from compounds of formula A or B as described above.

According to a third aspect of the invention there is provided a substance or composition for use in a method of treating a subject who has been infected by HIV, the substance or composition including a compound selected from compounds of formula A or B as described above.

According to a fourth aspect of the invention, there is provided the use of a compound selected from compounds of formula A or B as described above in the manufacture of a medicament for the treatment of a subject infected with HIV.

The compounds of the invention have been found to have activity against the enzyme reverse transcriptase in the μ-molar range. In addition these compounds have been found to be active against HIV in the whole cell PBMC or MAGI anti-HIV assay in the μM to nM range.

According to a fifth aspect of the invention there is provided a method of treating a subject who has been infected by HIV, the method including administering to a subject in need of treatment a compound selected from compounds of formula A or B as described above.

The compounds of the invention can readily be prepared in one step by an acid-catalysed three-component coupling reaction as shown in Scheme 1 in which a 2-aminopyridine or a substituted 2-aminopyridine, in which R, R¹, R², R³, R⁴and R⁵are as hereinbefore described, is reacted with an aldehyde and an isonitrile in the presence of montmorillonite K-10 clay or any other suitable acid catalyst at 95-100° C. for 5-8 hours under conventional heating or 15-30 min under microwave irradiation. The product is generally isolated by column chromatography.

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Thus according to a sixth aspect of the invention, there is provided a method of synthesising a compound selected from compounds of formula A or B as described above, which includes the step of condensing a 2-aminopyridine or a substituted 2-aminopyridine of the formula

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or 2-aminopyrimidine with an aldehyde of the formula R¹CHO and an isocyanide of the formula RNC in which R, R¹, R², R³, R⁴, R⁵and R⁶are as described above.

Examples of the compounds of the invention are set out in Scheme 2.

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The invention is now described, by way of example with reference to the following Examples.

All compounds were prepared by one of four methods

METHOD 1

The appropriate 2-aminopyridine (1.33 mmol), aldehyde (1.33 mmol) and isocyanide (1.36 mmol) in dioxane (2.5 ml) were heated in the presence of montmorillonite K-10 clay (250 mg) for 5-8 h at 95-100° C. After reaction, the liquid was filtered from the clay and the clay was rinsed with dioxane or ethyl acetate (2×2.5 ml). The solvent was removed in vacuo and the residue purified by column chromatography (elution hexane:ethyl acetate) to afford the required product.

Method 1 applies to compounds: 1-15, 17-31, 33-41, 43, 49-64, 67-77, 106-110, 112-115 and 117-183.

METHOD 2

As for method 1, but instead of heating, the reaction was stirred at room temperature for 48 h.

Method 2 applies to compounds: 45-47

METHOD 3

As for method 1, but instead of conventional heating, reaction components were reacted under microwave irradiation at 150 W and 100° C. for 15-30 min in a sealed pressure tube.

Method 3 applies to compounds: 42, 44, 48, 65, 66, 78-105, 111, 116, 186-194. In the case of the pyrimidine 193, the appropriate 2-aminopyrimidine (1.33 mmol) and aldehyde (2.66 mmol) were microwaved at 150 W power and 150° C. for 35 min without solvent. Isocyanide (1.60 mmol), dioxane (1.5 ml) and montmorillonite K-10 clay (250 mg) were then added and irradiated at 150 W and 100° C. for 25 min. After reaction, the liquid was filtered from the clay and the clay was rinsed with dioxane or ethyl acetate.

The solvent was removed in vacuo and the residue purified by column chromatography (elution ethyl acetate) to afford the required product.

METHOD 4

Imidazo[1,2-a]pyridines prepared by method 1 or 3 were further modified to produce compounds 16, 32, 184 and 185. Preparations are described below.

N-butyl-N-(2-isopropylimidazo[1,2-a]pyridin-3-yl)acetamide 16

N-butyl-2-isopropylimidazo[1,2-a]pyridin-3-amine 5 (250 mg, 1.08 mmol) was reacted with acetyl chloride (2 eq., 2.16 mmol, 154 μl) in the presence of K₂CO₃(2 eq., 2.16 mmol, 299 mg) in acetonitrile (10 ml) at room temperature. The reaction progress was monitored by TLC. Purification of the product was achieved by column chromatography, eluting with ethyl acetate:hexane.

N-butyl-N-ethyl-2-isopropylimidazo[1,2-a]pyridin-3-amine 32

N-butyl-N-(2-isopropylimidazo[1,2-a]pyridin-3-yl)acetamide 16 (287 mg, 1.05 mmol) was reacted with LiAlH₄(2 eq., 2.10 mmol, 80 mg) in THF (10 ml) at room temperature. Progress of the reaction was monitored by TLC. Aqueous NaOH solution was used to quench the reaction. Solids were filtered and washed with ethyl acetate and the product was purified by column chromatography, eluting with ethyl acetate.

2-(2-chlorophenyl)-N-cyclohexyl-5-phenoxyimidazo[1,2-a]pyridin-3-amine 184

Phenol (40.43 mg, 0.687 mmol) was dissolved in DMF (5 ml) and sodium metal (10.31 mg, 0.687 mmol) was added portion-wise. 5-Bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine 42 (139.1 mg, 0.344 mmol) was added to this sodium phenoxide solution and heated at 90° C. for 4 h. The reaction was quenched with water and extracted into ethyl acetate. The product was purified by column chromatography, elution ethyl acetate:hexane.

2-(2-chlorophenyl)-N-cyclohexyl-5-ethoxyimidazo[1,2-a]pyridin-3-amine 185

5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine 42 (152 mg, 0.376 mmol) was added to sodium ethoxide [generated in situ by addition of sodium metal (17.32 mg) to absolute ethanol (10 ml)]. The mixture was heated under reflux for 8 h. Excess solvent was removed in vacuo and the resultant mixture was treated with water before been extracted into ethyl acetate, dried over magnesium sulphate and filtered. Excess solvent was removed under reduced pressure to give an oil that was purified by column chromatography, eluting with hexane:ethyl acetate.

The analytical data of compounds 1-194 are set out below.

1 MLB133-607A N-cyclohexyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.05-7.94 (m, 1H), 7.46-7.33 (m, 1H), 7.01 (ddd, J=1.3, 6.7, 9.0, 1H), 6.69 (td, J=1.0, 6.7, 1H), 3.07-2.67 (m, 2H), 2.11-1.82 (m, 3H), 1.82-1.67 (m, 2H), 1.67-1.48 (m, 1H), 1.41-1.10 (m, 5H), 1.05 (dt, J=4.1, 5.2, 2H), 1.01-0.85 (m, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 141.22, 140.49, 124.82, 122.67, 121.94, 116.62, 110.82, 57.24, 34.37, 25.85, 24.94, 8.18, 7.73.

HRMS (ESI): m/z 256.1810 (M+H)⁺; calc. for C₁₆H₂₂N₃: 256.1814.

2 MLB133-607C N-cyclohexyl-2-(2-(methylthio)ethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.10-7.94 (m, 1H), 7.48-7.38 (m, 1H), 7.06 (ddd, J=1.3, 6.6, 9.0, 1H), 6.72 (td, J=1.1, 6.8, 1H), 3.20-2.78 (m, 6H), 2.18-2.00 (m, 3H), 1.76 (ddt, J=6.2, 10.2, 18.4, 5H), 1.41-1.03 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.43, 137.54, 125.25, 123.10, 122.53, 116.90, 111.11, 57.16, 34.43, 34.35, 27.81, 25.79, 24.91, 15.87.

HRMS (ESI): m/z 290.1684 (M+H)⁺; calc. for C₁₆H₂₄N₃S: 290.1691.

3 MLB133-608A 2-sec-butyl-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.14-7.93 (m, 1H), 7.48 (dt, J=1.3, 9.5, 1H), 7.04 (ddd, J=1.2, 6.7, 8.8, 1H), 6.71 (td, J=1.1, 6.9, 1H), 3.10-2.63 (m, 2H), 2.12-1.48 (m, 9H), 1.48-1.06 (m, 10H), 1.06-0.90 (m, 2H), 0.85 (t, J=7.3, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 143.77, 141.75, 124.39, 123.01, 122.71, 117.13, 111.12, 57.58, 34.55, 34.51, 33.63, 30.16, 26.09, 25.23, 25.15, 21.07, 12.87.

HRMS (ESI): m/z 272.2127 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

4 MLB133-609A N-cyclohexyl-2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (d, J=6.9, 1H), 7.52 (d, J=9.1, 1H), 7.18-7.05 (m, 1H), 6.78 (td, J=0.7, 6.8, 1H), 6.63-6.55 (m, 1H), 4.79-3.86 (m, 1H), 3.17-2.91 (m, 1H), 2.48 (s, 3H), 2.03-1.46 (m, 5H), 1.46-0.91 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 168.61, 159.55, 141.64, 129.39, 123.54, 123.02, 117.87, 111.94, 100.67, 56.38, 34.07, 25.70, 25.08, 12.21.

HRMS (ESI): m/z 297.1701 (M+H)⁺; calc. for C₁₇H₂₁N₄O: 297.1715.

5 MLB133-616C N-butyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.92 (d, J=6.8, 1H), 7.56-7.30 (m, 1H), 6.97 (ddd, J=0.9, 6.7, 8.6, 1H), 6.64 (td, J=0.6, 6.7, 1H), 3.24-2.97 (m, 1H), 2.90 (t, J=6.8, 3H), 1.65-1.34 (m, 4H), 1.30 (d, J=6.9, 6H), 0.87 (t, J=7.1, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 143.98, 141.19, 124.52, 122.64, 122.08, 117.08, 110.96, 48.96, 32.90, 26.45, 22.80, 20.22, 13.92.

HRMS (ESI): m/z 232.1808 (M+H)⁺; calc. for C₁₄H₂₂N₃: 232.1814.

6 MLB133-623B N-cyclohexyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.02 (d, J=6.8, 1H), 7.49 (d, J=8.9, 1H), 7.07-6.95 (m, 1H), 6.72 (dd, J=3.7, 9.7, 1H), 3.31-3.01 (m, 1H), 2.85 (ddd, J=5.2, 7.7, 10.2, 2H), 2.00-1.51 (m, 5H), 1.36 (d, J=6.9, 6H), 1.22 (dt, J=7.3, 12.7, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 144.66, 141.40, 123.06, 122.76, 122.44, 117.00, 110.94, 57.23, 34.30, 26.20, 25.85, 24.95, 22.83.

HRMS (ESI): m/z 258.1963 (M+H)⁺; calc. for C₁₆H₂₄N₃: 258.1970.

7 MLB133-624B 6-chloro-N-cyclohexyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.11-7.98 (m, 1H), 7.51-7.34 (m, 1H), 7.00 (ddd, J=0.7, 2.1, 9.5, 1H), 3.26-2.99 (m, 1H), 2.99-2.65 (m, 2H), 2.11-1.52 (m, 5H), 1.48-1.28 (m, 6H), 1.28-1.07 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 146.07, 139.73, 124.02, 123.66, 120.39, 119.45, 117.36, 57.23, 34.26, 26.28, 25.78, 24.91, 22.72.

HRMS (ESI): m/z 292.1581 (M+H)⁺; calc. for C₁₆H₂₃N₃Cl: 292.1581.

8 MLB133-641A 2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.17 (dt, J=1.0, 6.9, 1H), 7.70 (dd, J=3.0, 6.4, 1H), 7.62-7.52 (m, 1H), 7.52-7.29 (m, 3H), 7.16 (ddd, J=1.1, 6.6, 9.0, 1H), 6.82 (td, J=0.9, 6.7, 1H), 3.29 (d, J=6.7, 1H), 2.68 (s, 1H), 1.88-1.31 (m, 5H), 1.30-0.77 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.56, 135.04, 133.98, 132.56, 129.42, 129.07, 126.86, 126.33, 123.66, 122.83, 117.52, 111.55, 56.41, 33.87, 25.67, 24.60.

HRMS (ESI): m/z 326.1440 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

9 MLB133-628A N-cyclohexyl-2-ethylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (d, J=6.8, 1H), 7.45 (d, J=9.2, 1H), 7.17-6.89 (m, 1H), 6.71 (t, J=6.8, 1H), 2.75 (m+dd, J=7.6, 15.1, 4H), 2.08-1.46 (m, 5H), 1.34 (t, J=7.5, 3H), 1.27-1.02 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.52, 140.82, 124.27, 123.22, 122.67, 117.02, 111.34, 57.42, 34.55, 26.09, 25.18, 20.74, 14.26.

HRMS (ESI): m/z 244.1809 (M+H)⁺; calc. for C₁₅H₂₂N₃: 244.1814.

10 MLB133-616B 2-isopropyl-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.15 (d, J=6.7, 1H), 7.47 (d, J=9.0, 1H), 7.17-6.91 (m, 1H), 6.68 (t, J=6.7, 1H), 3.32-2.96 (m, 1H), 2.96-2.37 (m, 1H), 1.35 (d, J=6.8, 6H), 1.15 (d, J=8.1, 6H), 1.07 (d, J=10.9, 10H).

¹³C NMR (50 MHz, CDCl₃) δ 146.77, 142.18, 123.36, 122.99, 121.43, 116.91, 110.57, 59.26, 56.93, 31.97, 31.82, 29.23, 26.12, 22.89.

HRMS (ESI): m/z 288.2426 (M+H)⁺; calc. for C₁₈H₃₀N₃: 288.2440.

11 MLB133-616A 2-isopropyl-N-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.98 (d, J=6.8, 1H), 7.48 (d, J=9.0, 1H), 7.04 (dd, J=6.5, 8.5, 1H), 6.71 (t, J=6.9, 1H), 3.20-3.05 (m, 2H), 2.96 (t, J=7.0, 2H), 1.58 (ddd, J=3.7, 7.9, 14.3, 2H), 1.42-1.10 (m, 10H), 0.90 (t, J=7.0, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 143.89, 141.17, 124.52, 122.69, 122.08, 117.05, 111.00, 49.25, 30.50, 29.23, 26.44, 22.79, 22.55, 14.02.

HRMS (ESI): m/z 246.1950 (M+H)⁺; calc. for C₁₅H₂₄N₃: 246.1970.

12 MLB133-640A 4-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)-2-ethoxyphenol

¹H NMR (200 MHz, CDCl₃) δ 8.09 (d, J=6.9, 1H), 7.74-7.60 (m, 1H), 7.60-7.37 (m, 2H), 7.20-7.03 (m, 1H), 6.98 (d, J=8.2, 1H), 6.75 (t, J=7.1, 1H), 4.35-4.04 (m, 3H), 3.36-2.68 (m, 2H), 1.95-1.52 (m, 5H), 1.45 (t, J=6.9, 3H), 1.37-0.97 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 146.08, 145.42, 141.38, 136.83, 126.87, 124.06, 123.53, 122.54, 119.92, 117.13, 114.30, 111.34, 111.17, 64.60, 56.83, 34.24, 25.79, 24.85, 15.00.

HRMS (ESI): m/z 352.2025 (M+H)⁺; calc. for C₂₁H₂₆N₃O₂: 352.2025.

13 MLB133-635C 2-cyclopropyl-5,7-dimethyl-N-(naphthalen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.73 (d, J=8.7, 2H), 7.55 (d, J=8.2, 1H), 7.46-7.07 (m, 3H), 6.94 (dd, J=2.3, 8.8, 1H), 6.73 (d, J=1.4, 1H), 6.26 (s, 1H), 5.58 (s, 1H), 2.62 (s, 3H), 2.33 (s, 3H), 1.94 (ddd, J=5.1, 8.5, 13.5, 1H), 1.16-0.97 (m, 2H), 0.87 (ddd, J=3.8, 6.3, 11.8, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 145.76, 145.18, 144.78, 135.27, 134.89, 134.43, 129.52, 128.25, 127.63, 126.48, 126.12, 122.70, 118.67, 116.19, 115.53, 113.68, 107.06, 20.93, 18.76, 7.83, 7.54.

HRMS (ESI): m/z 328.1803 (M+H)⁺; calc. for C₂₂H₂₂N₃: 328.1814.

14 MLB133-627A N-isopropyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.14-8.05 (m, 1H), 7.97 (d, J=8.9, 2H), 7.51 (dd, J=0.5, 8.9, 1H), 7.17-7.04 (m, 1H), 6.98 (d, J=8.9, 2H), 6.74 (td, J=0.9, 6.7, 1H), 3.84 (s, 3H), 3.40 (td, J=7.2, 13.1, 1H), 3.16-2.79 (m, 1H), 1.08 (d, J=6.3, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 158.95, 141.59, 138.21, 128.31, 127.21, 123.61, 122.54, 117.22, 113.95, 111.34, 55.28, 49.12, 23.45.

HRMS (ESI): m/z 282.1602 (M+H)⁺; calc. for C₁₇H₂₀N₃O: 282.1606.

15 MLB133-640C N-cyclohexyl-5,7-dimethyl-2-propylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.05 (s, 1H), 6.20 (s, 1H), 2.83 (s, 3H), 2.61 (dd, J=8.7, 16.6, 4H), 2.28 (s, 3H), 1.98-1.50 (m, 7H), 1.16 (s, 5H), 0.98 (t, J=7.3, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 143.53, 140.95, 135.08, 133.70, 125.46, 115.34, 113.67, 59.57, 33.61, 29.74, 26.01, 25.17, 22.71, 20.77, 19.51, 14.33.

HRMS (ESI): m/z 286.2284 (M+H)⁺; calc. for C₁₈H₂₈N₃: 286.2283.

16 DG120-034 N-butyl-N-(2-isopropylimidazo[1,2-a]pyridin-3-yl)acetamide

¹H NMR (200 MHz, DMSO-d₆) δ 8.13 (d, J=6.3, 1H), 7.55 (d, J=9.3, 1H), 7.45-7.19 (m, 1H), 6.96 (t, J=6.7, 1H), 3.73-3.26 (m, 11H), 3.10-2.78 (m, 1H), 2.65-2.42 (m, 1H), 1.73 (s, 1H), 1.63 (s, 2H), 1.54-1.32 (m, 3H), 1.26 (t, J=6.7, 6H), 0.82 (t, J=6.9, 3H).

¹³C NMR (50 MHz, DMSO-d₆) δ 175.26, 171.14, 170.96, 146.57, 141.97, 124.82, 122.51, 118.46, 116.80, 112.58, 47.01, 30.61, 29.99, 25.61, 24.08, 22.44, 22.01, 21.82, 21.74, 20.74, 19.56, 13.59.

17 MLB133-628B N,2-bis(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, DMSO-d₆) δ 8.13-7.79 (m, 3H), 7.55 (dd, J=8.8, 14.7, 1H), 7.39-7.16 (m, 1H), 7.04-6.83 (m, 3H), 6.76 (d, J=8.8, 2H), 6.45 (d, J=8.8, 2H), 3.77 (s, 3H), 3.64 (s, 3H).

¹³C NMR (50 MHz, DMSO-d₆) δ 158.66, 152.22, 141.40, 139.19, 139.12, 137.35, 127.65, 126.18, 124.64, 122.81, 116.70, 114.97, 113.79, 113.41, 111.83, 55.19, 55.03.

HRMS (ESI): m/z 346.1548 (M+H)⁺; calc. for C₂₁H₂₀N₃O₂: 346.1556.

18 MLB133-615B N-benzyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.99 (d, J=6.8, 1H), 7.52 (d, J=8.9, 1H), 7.35 (s, 5H), 7.19-6.97 (m, 1H), 6.72 (t, J=6.7, 1H), 4.15 (d, J=3.7, 2H), 3.35-3.17 (m, 1H), 3.17-2.94 (m, 1H), 1.33 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 144.54, 141.34, 139.39, 128.60, 128.22, 127.54, 123.84, 122.89, 122.05, 117.14, 111.10, 53.33, 26.49, 22.74.

HRMS (ESI): m/z 266.1637 (M+H)⁺; calc. for C₁₇H₂₀N₃: 266.1657.

19 MLB133-607B N-cyclohexyl-2-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (d, J=7.3, 1H), 7.49 (d, J=9.0, 1H), 7.17-6.92 (m, 1H), 6.71 (t, J=6.8, 1H), 3.34-3.03 (m, 1H), 3.02-2.64 (m, 2H), 2.12-1.82 (m, 8H), 1.82-1.44 (m, 5H), 1.44-1.00 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 142.71, 141.52, 124.07, 122.63, 122.31, 116.99, 110.83, 57.19, 37.61, 34.33, 33.53, 26.04, 25.88, 25.00.

HRMS (ESI): m/z 284.2125 (M+H)⁺; calc. for C₁₈H₂₆N₃: 284.2127.

20 MLB133-615C 2-isopropyl-N-(naphthalen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.93-7.79 (m, 1H), 7.73 (d, J=8.7, 2H), 7.69-7.58 (m, 1H), 7.51 (d, J=8.1, 1H), 7.43-7.12 (m, 3H), 6.95 (dd, J=2.4, 8.8, 1H), 6.72 (td, J=1.1, 6.8, 1H), 6.66 (d, J=2.2, 1H), 5.73 (s, 1H), 3.37-3.03 (m, 1H), 1.37 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 148.20, 143.18, 142.59, 134.74, 129.56, 128.42, 127.63, 126.54, 126.07, 124.12, 122.90, 122.44, 117.36, 116.97, 116.27, 111.68, 106.69, 26.79, 22.31.

HRMS (ESI): m/z 302.1640 (M+H)⁺; calc. for C₂₀H₂₀N₃: 302.1657.

21 MLB133-608C N-cyclohexyl-2-(2,5-dimethoxytetrahydrofuran-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.09-7.90 (m, 1H), 7.53-7.37 (m, 1H), 7.15-6.95 (m, 1H), 6.80-6.64 (m, 1H), 5.40-4.99 (m, 2H), 3.81-3.62 (m, 1H), 3.44 (dd, J=4.2, 10.4, 6H), 3.04 (dd, J=5.3, 10.8, 1H), 2.85 (td, J=5.5, 9.5, 1H), 2.72-2.41 (m, 1H), 2.41-2.19 (m, 1H), 1.99-1.37 (m, 5H), 1.17 (dq, J=7.5, 13.3, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 147.44, 141.52, 138.14, 137.54, 136.67, 125.76, 123.16, 122.83, 122.49, 122.25, 117.18, 117.03, 116.85, 113.69, 111.51, 111.17, 109.68, 109.13, 105.97, 105.38, 104.83, 104.50, 57.13, 57.08, 56.13, 55.74, 54.92, 42.71, 41.75, 38.71, 36.36, 34.34, 34.18, 34.11, 25.73, 25.01, 24.89, 24.85.

HRMS (ESI): m/z 346.2094 (M+H)⁺; calc. for C₁₉H₂₈N₃O₃: 346.2131.

22 MLB133-623A N-cyclohexyl-6-fluoro-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.96-7.76 (m, 1H), 7.36 (dd, J=5.0, 9.7, 1H), 6.99-6.70 (m, 1H), 3.22-2.93 (m, 1H), 2.77 (s, 2H), 1.92-1.41 (m, 5H), 1.28 (d, J=6.9, 6H), 1.22-0.87 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 155.15, 150.48, 146.47, 138.82, 138.11, 124.36, 117.28, 117.10, 114.49, 113.97, 109.17, 108.35, 57.01, 34.11, 26.20, 25.63, 24.75, 22.61.

HRMS (ESI): m/z 276.1858 (M+H)⁺; calc. for C₁₆H₂₃N₃F: 276.1876.

23 MLB133-623C N-cyclohexyl-2-isopropyl-5,7-dimethylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.11 (s, 1H), 6.20 (s, 1H), 3.08 (dt, J=6.9, 13.7, 1H), 2.83 (s, 3H), 2.64 (s, 1H), 2.26 (s, 3H), 1.89-1.51 (m, 5H), 1.32 (d, J=6.9, 6H), 1.26-0.97 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 146.49, 143.95, 135.39, 133.92, 124.12, 115.64, 115.61, 114.12, 114.09, 59.82, 33.80, 26.27, 26.19, 25.45, 22.99, 21.03, 19.85.

HRMS (ESI): m/z 286.2277 (M+H)⁺; calc. for C₁₈H₂₈N₃: 286.2283.

24 MLB133-628C 2-cyclopropyl-N-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.04-7.91 (m, 1H), 7.48-7.34 (m, 1H), 7.14-6.92 (m, 1H), 6.83-6.60 (m, 1H), 3.03 (t, J=7.1, 3H), 1.99 (ddd, J=5.2, 8.4, 13.5, 1H), 1.74-1.49 (m, 2H), 1.49-1.17 (m, 4H), 1.15-1.00 (m, 2H), 1.00-0.75 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.31, 139.89, 126.43, 122.93, 121.98, 116.99, 111.18, 49.36, 30.81, 29.51, 22.83, 14.30, 8.33, 7.81.

HRMS (ESI): m/z 244.1819 (M+H)⁺; calc. for C₁₅H₂₂N₃: 244.1814.

25 MLB133-624A 8-(benzyloxy)-N-cyclohexyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.66 (dd, J=1.0, 6.7, 1H), 7.62-7.45 (m, 2H), 7.45-7.20 (m, 3H), 6.65-6.44 (m, 1H), 6.44-6.20 (m, 1H), 5.41 (s, 2H), 3.32-3.05 (m, 1H), 3.05-2.58 (m, 2H), 2.03-1.54 (m, 5H), 1.42 (d, J=6.9, 6H), 1.35-1.05 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 147.73, 144.20, 137.20, 128.73, 127.95, 127.19, 124.30, 116.01, 110.72, 102.01, 70.82, 57.54, 34.55, 26.83, 26.13, 25.23, 23.07.

HRMS (ESI): m/z 364.2351 (M+H)⁺; calc. for C₂₃H₃₀N₃O: 364.2389.

26 MLB133-627C₂-(4-methoxyphenyl)-N-(naphthalen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.98 (d, J=8.6, 2H), 7.87-7.57 (m, 4H), 7.57-7.10 (m, 4H), 6.99 (dd, J=2.3, 8.7, 1H), 6.86 (d, J=8.6, 2H), 6.78-6.63 (m, 2H), 5.93 (s, 1H), 3.78 (s, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 159.65, 143.04, 142.80, 139.81, 138.46, 135.12, 130.15, 128.87, 128.59, 127.94, 126.87, 126.47, 126.27, 125.11, 123.31, 122.93, 117.65, 116.66, 114.29, 112.25, 107.30, 55.47.

HRMS (ESI): m/z 366.1577 (M+H)⁺; calc. for C₂₄H₂₀N₃O: 366.1606.

27 MLB133-629B N-benzyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.00-7.85 (m, 3H), 7.60-7.45 (m, 1H), 7.40-7.25 (m, 5H), 7.15-6.95 (m, 3H), 6.75-6.65 (m, 1H), 4.20 (d, 2H), 3.85 (s, 3H), 3.50-3.35 (m, 1H).

¹³C NMR (50 MHz, CDCl₃) δ 159.02, 156.38, 141.43, 139.05, 129.60, 128.58, 128.23, 128.17, 128.09, 127.53, 123.59, 122.14, 117.21, 114.04, 111.37, 55.26, 52.37.

HRMS (ESI): m/z 330.1591 (M+H)⁺; calc. for C₂₁H₂₀N₃O: 330.1606.

28 MLB133-634A N-cyclohexyl-2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.18-7.78 (m, 1H), 7.57-7.26 (m, 1H), 7.10-6.82 (m, 1H), 6.63 (td, J=0.9, 6.7, 1H), 6.11 (ddd, J=1.3, 3.2, 4.7, 1H), 3.06 (td, J=1.3, 5.8, 1H), 3.01-2.72 (m, 2H), 2.61-2.30 (m, 3H), 2.25-2.03 (m, 1H), 1.92-1.44 (m, 5H), 1.32 (s, 3H), 1.30-1.01 (m, 6H), 0.90 (s, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 141.98, 138.46, 137.13, 123.36, 122.70, 121.85, 117.41, 111.35, 57.61, 44.20, 41.16, 38.12, 34.50, 34.39, 32.50, 32.12, 26.63, 26.10, 25.21, 21.54.

HRMS (ESI): m/z 336.2413 (M+H)⁺; calc. for C₂₂H₃₀N₃: 336.2440.

29 MLB133-627B N-butyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.06-7.92 (m, 1H), 7.45-7.36 (m, 1H), 7.02 (ddd, J=1.3, 6.7, 9.0, 1H), 6.70 (td, J=1.1, 6.8, 1H), 3.25-2.79 (m, 3H), 1.99 (ddd, J=5.1, 8.3, 10.0, 1H), 1.73-1.31 (m, 5H), 1.15-0.73 (m, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 141.04, 139.62, 126.15, 122.71, 121.72, 116.72, 110.95, 48.81, 32.95, 20.22, 13.95, 8.05, 7.56.

HRMS (ESI): m/z 230.1646 (M+H)⁺; calc. for C₁₄H₂₀N₃: 230.1657.

30 MLB133-615A 2-isopropyl-N-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.87-7.75 (m, 1H), 7.64-7.50 (m, 1H), 7.23-7.02 (m, 1H), 6.90-6.61 (m, 3H), 6.56-6.31 (m, 2H), 5.23 (s, 1H), 3.73 (s, 3H), 3.27-3.01 (m, 1H), 1.32 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 153.24, 147.91, 142.37, 139.29, 123.85, 122.40, 117.83, 117.46, 115.05, 114.08, 111.51, 55.70, 26.70, 22.33.

HRMS (ESI): m/z 282.1582 (M+H)⁺; calc. for C₁₇H₂₀N₃O: 282.1606.

31 MLB133-640B N-cyclohexyl-2-octylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (d, J=6.8, 1H), 7.44 (d, J=8.4, 1H), 7.12-6.92 (m, 1H), 6.70 (t, J=6.7, 1H), 2.98-2.77 (m, 2H), 2.77-2.58 (m, 2H), 1.95-1.48 (m, 7H), 1.48-1.00 (m, 15H), 0.98-0.72 (m, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 141.35, 139.73, 124.40, 122.69, 122.37, 116.85, 110.89, 57.21, 34.33, 31.91, 29.85, 29.67, 29.50, 29.29, 27.51, 25.86, 24.93, 22.68, 14.09.

HRMS (ESI): m/z 328.2747 (M+H)⁺; calc. for C₂₁H₃₄N₃: 328.2753.

32 DG120-036 N-butyl-N-ethyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.99 (d, J=6.8, 1H), 7.49 (d, J=9.0, 1H), 7.12-6.98 (m, 1H), 6.72 (t, J=6.3, 1H), 3.16 (dt, J=7.0, 13.8, 1H), 2.99 (dd, J=6.3, 12.5, 3H), 2.88-2.70 (m, 1H), 1.74-1.40 (m, 5H), 1.38 (d, J=6.9, 7H), 0.95 (t, J=7.0, 4H).

33 MLB133-608B N-cyclohexyl-2-(4-(dimethylamino)phenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.14-8.04 (m, 1H), 7.94 (d, J=8.7, 2H), 7.54-7.47 (m, 1H), 7.07 (ddd, J=1.3, 6.6, 8.9, 1H), 6.81 (d, J=8.9, 1H), 6.73 (td, J=0.9, 6.9, 2H), 3.01 (s, 8H), 1.93-1.43 (m, 5H), 1.43-0.93 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 149.65, 141.40, 137.26, 131.84, 127.83, 123.07, 122.78, 122.41, 116.87, 112.33, 110.95, 56.80, 40.42, 34.15, 25.79, 24.83.

34 MLB133-629A 2-(4-methoxyphenyl)-N-(2,4,4-trimethylpentan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.21 (d, J=6.9, 1H), 7.79 (d, J=8.9, 2H), 7.51 (d, J=9.0, 1H), 7.10 (dd, J=7.2, 8.5, 1H), 6.97 (d, J=8.9, 2H), 6.75 (t, J=6.8, 1H), 3.85 (s, 3H), 3.34-2.95 (m, 1H), 1.60 (s, 2H), 1.04 (s, 9H), 0.96 (s, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 159.21, 142.18, 140.03, 129.78, 128.35, 123.91, 123.70, 123.01, 117.39, 113.94, 111.32, 60.88, 57.35, 55.53, 32.15, 32.02, 29.26.

HRMS (ESI): m/z 352.2379 (M+H)⁺; calc. for C₂₂H₃₀N₃O: 352.2389.

35 MLB133-634B (5-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)furan-2-yl)methanol

¹H NMR (400 MHz, CDCl₃) δ 8.07-8.02 (m, 1H), 7.49-7.45 (m, 1H), 7.14-7.08 (m, 1H), 6.80-6.71 (m, 2H), 6.33 (d, 1H), 4.66 (s, 2H), 3.49 (br s, 1H), 2.95-2.90 (m, 2H), 1.87-1.82 (m, 2H), 1.75-1.68 (m, 2H), 1.60-1.55 (m, 1H), 1.35-1.10 (m, 5H).

¹³C NMR (101 MHz, DMSO-d₆) δ 154.38, 148.63, 140.53, 127.56, 125.49, 123.72, 123.10, 116.47, 111.52, 108.47, 106.98, 56.25, 55.81, 33.54, 25.36, 24.48.

HRMS (ESI): m/z 312.1679 (M+H)⁺; calc. for C₁₈H₂₂N₃O₂: 312.1712.

36 MLB133-636A 6-chloro-N-cyclohexyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.10-7.93 (m, 1H), 7.41-7.27 (m, 1H), 7.08-6.89 (m, 1H), 3.19-2.57 (m, 2H), 2.07-1.84 (m, 3H), 1.84-1.68 (m, 2H), 1.68-1.45 (m, 1H), 1.44-1.11 (m, 5H), 1.11-0.80 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 141.94, 139.49, 125.32, 123.91, 119.89, 119.36, 116.94, 57.21, 34.34, 25.79, 24.91, 8.20, 7.93.

HRMS (ESI): m/z 290.1408 (M+H)⁺; calc. for C₁₆H₂₁N₃Cl: 290.1424.

37 MR762-137.4 2-(3,4-dimethoxyphenyl)-N-(2-morpholinoethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.16 (d, J=7, 1H), 8.10 (m, 2H), 7.60 (m, 2H), 7.14-7.32 (m, 1H), 6.93 (br t, 1H), 4.14 (br s, 1H), 3.98 (s, 3H), 3.92 (s, 3H), 3.76 (t, 4H), 3.07-3.10 (m, 2H), 2.52-2.58 (m, 2H), 2.44 (t, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 149.6, 148.9, 138.7, 126.2, 126.0, 124.1, 122.5, 119.4, 117.3, 112.0, 111.4, 111.3, 110.0, 67.0, 58.7, 56.4, 56.2, 54.0, 44.3.

38 MLB133-649A N-cyclohexyl-2-(pentan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.93 (dt, J=1.0, 6.8, 1H), 7.39 (dt, J=0.9, 9.0, 1H), 6.93 (ddd, J=1.3, 6.7, 9.0, 1H), 6.59 (td, J=1.1, 6.7, 1H), 3.05-2.60 (m, 2H), 1.91-1.38 (m, 6H), 1.26 (d, J=6.9, 3H), 1.22-0.93 (m, 7H), 0.80 (t, J=7.2, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 143.69, 141.28, 123.68, 122.40, 122.21, 116.71, 110.57, 57.10, 39.10, 34.09, 31.11, 25.63, 24.75, 24.68, 20.86, 13.99.

HRMS (ESI): m/z 286.2251 (M+H)⁺; calc. for C₁₈H₂₈N₃: 286.2283.

39 MLB133-648B N-cyclohexyl-2-(2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.09 (dt, J=1.0, 6.7, 1H), 7.76 (d, J=8.5, 1H), 7.53 (d, J=9.0, 1H), 7.08 (ddd, J=1.3, 6.7, 9.1, 1H), 6.75 (td, J=1.1, 6.8, 1H), 6.67 (dd, J=2.4, 8.5, 1H), 6.58 (d, J=2.2, 1H), 3.87 (s, 6H), 3.70 (s, 3H), 2.87-2.40 (m, 1H), 2.01-1.27 (m, 4H), 1.27-0.75 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 160.67, 156.86, 132.32, 126.71, 123.30, 122.56, 116.96, 111.38, 105.81, 99.31, 67.09, 56.42, 56.12, 55.44, 34.15, 25.74, 24.83.

HRMS (ESI): m/z 352.2012 (M+H)⁺; calc. for C₂₁H₂₆N₃O₂: 352.2025.

40 MLB133-653B N-cyclohexyl-2-neopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (dt, J=1.0, 6.6, 1H), 7.46 (dt, J=1.0, 9.3, 1H), 7.03 (ddd, J=1.3, 6.6, 9.0, 1H), 6.70 (td, J=1.1, 6.8, 1H), 3.11-2.75 (m, 2H), 2.64 (s, 2H), 2.07-1.43 (m, 5H), 1.41-1.07 (m, 5H), 1.00 (s, 9H).

¹³C NMR (50 MHz, CDCl₃) δ 140.88, 137.31, 126.04, 122.44, 122.39, 116.98, 110.75, 56.84, 41.34, 34.50, 33.12, 29.85, 25.83, 24.96.

HRMS (ESI): m/z 286.2247 (M+H)⁺; calc. for C₁₈H₂₈N₃: 286.2283.

41 MLB133-655A N-cyclohexyl-2-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.06-7.96 (m, 1H), 7.51-7.35 (m, 1H), 7.04 (ddd, J=1.3, 6.7, 9.0, 1H), 6.71 (td, J=1.1, 6.8, 1H), 3.14-2.77 (m, 2H), 2.77-2.50 (m, 2H), 1.98-1.47 (m, 7H), 1.47-1.29 (m, 4H), 1.27-1.05 (m, 5H), 0.90 (t, J=6.9, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 141.32, 139.65, 124.40, 122.74, 122.36, 116.81, 110.92, 57.20, 34.32, 32.05, 29.35, 27.43, 25.84, 24.92, 22.57, 14.07.

HRMS (ESI): m/z 286.2270 (M+H)⁺; calc. for C₁₈H₂₈N₃: 286.2283.

42 DG 402-49706 5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 7.60 (d, J=2.9, 1H), 7.60-7.57 (m, 1H), 7.54 (d, J=1.8, 1H), 7.52 (d, J=1.8, 1H), 7.50-7.48 (m, 1H), 7.47 (d, J=2.5, 1H), 7.37-7.29 (m, 4H), 7.03-6.96 (m, 3H), 6.94 (t, J=4.1, 1H), 3.28 (d, J=6.2, 2H), 2.97-2.62 (m, 2H), 1.66 (d, J=12.4, 5H), 1.59-1.48 (m, 4H), 1.48-1.35 (m, 2H), 1.16-0.97 (m, 7H), 0.97-0.75 (m, 4H).

¹³C NMR (101 MHz, CDCl₃) δ 143.74, 138.16, 133.87, 133.32, 132.60, 129.50, 129.21, 128.45, 126.64, 123.78, 118.62, 117.34, 112.21, 58.29, 32.70, 25.73, 24.50.

HRMS (ESI): m/z 404.0516 (M+H)⁺; calc. for C₁₉H₂₀N₃ClBr: 404.0529.

43 DG 402-49651 2-(2-bromophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.43-7.97 (m, 3H), 7.64 (td, J=1.5, 7.7, 4H), 7.58-7.48 (m, 2H), 7.39 (td, J=1.3, 7.5, 2H), 7.31-7.21 (m, 2H), 7.21-7.13 (m, 2H), 7.11 (dd, J=1.3, 6.7, 1H), 6.80 (td, J=1.1, 6.7, 2H), 3.42-3.09 (m, 2H), 2.82-2.48 (m, 2H), 1.80-1.33 (m, 12H), 1.21-0.81 (m, 13H).

¹³C NMR (50 MHz, CDCl₃) δ 141.35, 136.12, 132.67, 132.50, 129.26, 127.26, 125.80, 123.51, 122.87, 122.79, 117.53, 111.46, 56.34, 33.80, 25.64, 24.51.

HRMS (ESI): m/z 370.0892 (M+H)⁺; calc. for C₁₉H₂₁N₃Br: 370.0919.

44 DG 402-49659 2-(2-chlorophenyl)-N-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.12 (dt, J=1.2, 6.9, 1H), 7.79-7.61 (m, 1H), 7.55 (dt, J=1.1, 9.1, 1H), 7.51-7.44 (m, 1H), 7.42-7.28 (m, 2H), 7.14 (ddd, J=1.3, 6.7, 9.1, 1H), 6.82 (td, J=1.1, 6.8, 1H), 3.30 (t, J=6.2, 1H), 2.83 (q, J=6.7, 2H), 1.95-1.64 (m, 1H), 1.42-1.24 (m, 2H), 1.24-1.05 (m, 3H), 0.90-0.60 (m, 3H).

¹³C NMR (101 MHz, CDCl₃) δ 141.47, 133.93, 132.84, 132.60, 129.48, 129.14, 126.87, 123.57, 122.60, 117.69, 111.62, 48.27, 30.02, 28.93, 22.38, 13.90.

HRMS (ESI): m/z 314.1414 (M+H)⁺; calc. for C₁₈H₂₁N₃Cl: 314.1424.

45 DG789-110 N-butyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.08 (dt, J=1.2, 6.8, 1H), 7.97-7.89 (m, 2H), 7.61-7.55 (m, 1H), 7.15 (ddd, J=1.3, 6.7, 9.0, 1H), 6.99-6.94 (m, 2H), 6.82 (td, J=1.1, 6.8, 1H), 3.85 (s, 4H), 3.02 (t, J=7.1, 2H), 1.58 (dt, J=6.9, 14.4, 2H), 1.41 (dq, J=7.2, 14.3, 2H), 0.92 (t, J=7.3, 3H).

¹³C NMR (101 MHz, CDCl₃) δ 159.10, 140.57, 134.37, 128.20, 125.71, 125.54, 124.57, 122.43, 116.53, 114.03, 112.06, 55.22, 47.92, 32.78, 20.18, 13.89.

HRMS (ESI): m/z 296.1735 (M+H)⁺; calc. for C₁₈H₂₂N₃O: 296.1763.

46 DG789-112 2-(4-methoxyphenyl)-N-pentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.06 (dt, J=1.1, 6.8, 1H), 7.95-7.89 (m, 2H), 7.56 (d, J=9.0, 1H), 7.13 (ddd, J=1.3, 6.7, 9.0, 1H), 7.01-6.94 (m, 2H), 6.80 (td, J=1.1, 6.8, 1H), 3.85 (s, 4H), 3.01 (t, J=7.1, 2H), 1.58 (dd, J=7.6, 14.8, 2H), 1.34 (ddd, J=5.1, 9.9, 19.4, 4H), 0.89 (t, J=7.1, 3H).

¹³C NMR (101 MHz, CDCl₃) δ 159.04, 140.79, 134.74, 128.20, 126.10, 125.52, 124.24, 122.35, 116.72, 114.01, 111.85, 55.22, 48.20, 30.36, 29.17, 22.47, 13.97.

HRMS (ESI): m/z 310.1906 (M+H)⁺; calc. for C₁₉H₂₄N₃O: 310.1919.

47 DG789-116 N-cyclopropyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine
48 DG 402-49760 5-chloro-2-(2-chlorophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 7.63-7.58 (m, 1H), 7.52-7.46 (m, 2H), 7.38-7.30 (m, 2H), 7.04 (dd, J=7.2, 9.0, 1H), 6.78 (dd, J=1.1, 7.2, 1H), 3.57-3.40 (m, 1H), 3.27 (d, J=5.7, 1H), 1.70-1.46 (m, 2H), 1.46-1.30 (m, 4H), 1.30-1.14 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 143.66, 137.58, 133.63, 133.36, 132.65, 129.50, 129.27, 126.64, 126.37, 126.13, 123.65, 116.80, 114.02, 61.91, 32.48, 22.98.

HRMS (ESI): m/z 346.0865 (M+H)⁺; calc. for C₁₈H₁₈N₃Cl₂: 346.0878.

49 MLB133-635A N-butyl-6-chloro-2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.08-7.95 (m, 1H), 7.46 (d, J=9.6, 1H), 7.06 (dd, J=2.0, 9.6, 1H), 6.56 (s, 1H), 4.54 (t, J=6.8, 1H), 3.07 (dd, J=6.9, 13.8, 2H), 2.48 (s, 3H), 1.73-1.50 (m, 2H), 1.50-1.22 (m, 2H), 0.92 (t, J=7.2, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 168.93, 159.22, 139.76, 131.08, 124.93, 124.54, 120.57, 120.51, 118.33, 100.50, 47.42, 32.64, 20.13, 13.85, 12.21.

HRMS (ESI): m/z 305.1180 (M+H)⁺; calc. for C₁₅H₁₈N₄ClO: 305.1169.

50 MLB133-634C N-benzyl-6-chloro-2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.98 (dd, J=0.9, 1.9, 1H), 7.48 (dd, J=0.8, 9.6, 1H), 7.44-7.22 (m, 5H), 7.08 (dd, J=2.0, 9.6, 1H), 6.61-6.54 (m, 1H), 4.80 (t, J=6.4, 1 H), 4.25 (d, J=6.5, 2H), 2.49 (d, J=11.7, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 169.36, 159.09, 140.09, 138.64, 130.45, 128.80, 128.50, 127.88, 125.78, 121.07, 120.93, 118.35, 100.84, 52.22, 12.49.

HRMS (ESI): m/z 339.0979 (M+H)⁺; calc. for C₁₈H₁₆N₄OCl: 339.1013.

51 MLB133-635B N-butyl-5,7-dimethyl-2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.09 (s, 1H), 6.56 (d, J=0.6, 1H), 6.25 (s, 1H), 3.98 (t, J=7.2, 1H), 3.09-2.73 (m, 5H), 2.45 (s, 3H), 2.26 (s, 3H), 1.76-1.50 (m, 2H), 1.38 (dq, J=7.1, 13.8, 2H), 0.90 (t, J=7.2, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 168.42, 159.50, 143.95, 135.77, 134.93, 132.46, 126.01, 116.10, 114.03, 100.75, 52.08, 31.99, 20.86, 20.19, 18.57, 13.93, 12.10.

HRMS (ESI): m/z 299.1869 (M+H)⁺; calc. for C₁₇H₂₃N₄O: 299.1872.

52 MLB133-636B N-benzyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.96 (d, J=6.8, 1H), 7.55-7.18 (m, 6H), 7.12-6.97 (m, 1H), 6.77-6.54 (m, 1H), 4.21 (s, 2H), 3.52-2.83 (m, 1H), 1.85 (ddd, J=5.1, 8.3, 9.9, 1H), 1.11-0.97 (m, 2H), 0.91 (dtd, J=2.1, 4.9, 7.3, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 139.53, 128.72, 128.55, 128.28, 127.88, 127.46, 122.92, 121.68, 116.70, 111.00, 107.42, 53.26, 8.00, 7.57.

HRMS (ESI): m/z 264.1477 (M+H)⁺; calc. for C₁₇H₁₈N₃: 264.1501.

53 MR762-137.15 N-cyclohexyl-2-(furan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.07 (dd, J=6.7, 1.2, 1H), 7.53 (d, J=9.0, 1H), 7.51 (d, J=1.6, 1H), 7.15 (ddd, J=9.0, 6.7, 1.2, 1H), 6.91 (d, J=3.3, 1H), 6.79 (td, J=6.7, 1.0, 1H), 6.55 (dd, J=3.3, 1.6, 1H), 3.62 (br s, 1H) 2.85-3.10 (m, 1H), 1.50-2.00, 1.05-1.45 (m, 9H).

¹³C NMR (50 MHz, CDCl₃) δ 149.72, 141.56, 141.37, 127.40, 125.45, 124.45, 122.81, 116.90, 111.91, 111.52, 106.98, 57.12, 34.13, 25.76, 25.01.

54 10061 N-cyclohexyl-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.11 (d, J=6.8, 2H), 8.02 (d, J=8.6, 2H), 7.16-7.08 (m, 1H), 7.02-6.98 (d, J=8.6, 2H), 6.80-6.73 (m, 1H), 3.87 (s, 3H), 1.80-1.59 (br m, 10H).

¹³C NMR (50 MHz, CDCl₃) δ 158.3, 141.6, 138.3, 137.1, 128.6, 127.3, 124.3, 123.9, 118.5, 117.3, 116.2, 57.1, 55.5, 34.4, 26.0, 25.1.

55 MR762-137.8 2-(furan-2-yl)-N-(2-morpholinoethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.07 (dd, J=6.4, 1.2, 1H), 7.51 (d, J=8.0, 1H), 7.45 (d, J=0.8, 1H), 7.11 (ddd, J=8.0, 6.4, 1.2, 1H), 6.89 (d, J=3.2, 1H), 6.78 (td, J=6.4, 0.8, 1H), 6.53 (dd, J=3.2, 1.2, 1H), 4.34 (br s, 1H), 3.76 (m 4H), 3.13 (t, J=6.0, 2H), 2.61 (t, J=6.4, 2H), 2.50 (br s, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 150.3, 141.7, 141.3, 126.9, 126.7, 123.9, 122.4, 117.3, 111.6, 111.5, 106.3, 67.0, 58.2, 53.5, 44.3.

56 MR762-137.11 N-cyclohexyl-2-(3,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (d, J=6.8, 1H), 7.71 (d, J=1.8, 1H), 7.60-7.48 (m, 2H), 7.12-6.94 (m, 1H), 6.90, (d, J=8.4, 1H), 3.97 (s, 3H), 3.91 (s, 3H), 3.20-2.81 (m, 2H), 1.83-1.21 (br m, 10H).

¹³C NMR (50 MHz, CDCl₃) 149.3, 148.7, 141.6, 136.7, 127.6, 124.4, 123.9, 122.8, 119.7, 117.3, 111.7, 111.4, 110.9, 67.3, 57.0, 56.2, 56.1, 34.5, 26.0, 25.1.

57 MLB133-639A 4-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)-2,6-dimethoxyphenol

¹H NMR (200 MHz, DMSO-d₆) δ 8.49-8.22 (m, 2H), 7.45 (d, J=8.8, 1H), 7.21-7.06 (m, 1H), 6.86 (t, J=6.7, 1H), 4.87-4.59 (m, 1H), 3.85 (s, 6H), 3.07-2.81 (m, 1H), 1.86-1.43 (m, 5H), 1.43-0.92 (m, 5H).

¹³C NMR (50 MHz, DMSO-d₆) δ 147.76, 140.11, 135.09, 134.79, 124.95, 124.41, 123.44, 123.03, 116.24, 110.93, 104.05, 56.18, 55.86, 33.58, 25.44, 24.40.

HRMS (ESI): m/z 368.1946 (M+H)⁺; calc. for C₂₁H₂₆N₃O₃: 368.1974.

58 MLB133-639C₂-(4-(benzyloxy)benzyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.10 (d, J=6.8, 1H), 8.01 (d, J=8.8, 2H), 7.59-7.27 (m, 7H), 7.13-7.00 (m, 2H), 6.76 (t, J=6.8, 1H), 5.13 (s, 2H), 2.98 (m, 1H), 1.75 (m, 5H), 1.47-0.97 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 158.10, 141.42, 136.97, 136.56, 129.52, 128.45, 128.28, 127.83, 127.43, 124.05, 123.51, 122.52, 117.07, 114.82, 111.27, 69.99, 56.77, 34.13, 25.73, 24.79.

HRMS (ESI): m/z 412.2364 (M+H)⁺; calc. for C₂₇H₃₀N₃O: 412.2389.

59 MLB133-639B 2-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)phenol

¹H NMR (200 MHz, DMSO-d₆+CD₃OD) δ 8.36 (d, J=6.8, 1H), 8.17 (dd, J=1.7, 8.1, 1H), 7.54 (d, 1H), 7.40-7.15 (m, 2H), 7.10-6.85 (m, 3H), 3.05-2.81 (m, 1H), 1.99-1.44 (m, 5H), 1.44-1.01 (m, 5H).

¹³C NMR (50 MHz, DMSO-d₆+CD₃OD) δ 156.77, 141.58, 135.94, 129.75, 129.14, 125.78, 125.08, 123.89, 119.89, 117.86, 116.87, 113.01, 57.65, 34.24, 26.43, 25.54.

HRMS (ESI): m/z 308.1767 (M+H)⁺; calc. for C₁₉H₂₂N₃O: 308.1763.

60 MLB133-649C N-cyclohexyl-2-(pentan-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.05 (dt, J=1.0, 6.8, 1H), 7.58-7.38 (m, 1H), 7.03 (ddd, J=1.3, 6.6, 9.0, 1H), 6.70 (td, J=1.1, 6.7, 1H), 3.20-2.72 (m, 1H), 2.72-2.42 (m, 1H), 1.99-1.44 (m, 9H), 1.41-1.01 (m, 6H), 0.80 (t, J=7.4, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 142.04, 141.60, 125.60, 122.61, 122.45, 116.96, 110.69, 57.56, 40.98, 34.25, 28.31, 25.86, 24.92, 12.62.

HRMS (ESI): m/z 286.2281 (M+H)⁺; calc. for C₁₈H₂₈N₃: 286.2283.

61 MLB133-648A N-cyclohexyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.49-8.21 (m, 4H), 8.07 (dt, J=1.0, 6.9, 1H), 7.55 (d, J=8.3, 1H), 7.18 (ddd, J=1.3, 6.7, 9.1, 1H), 6.83 (td, J=1.0, 6.8, 1H), 3.28-2.79 (m, 2H), 2.04-1.47 (m, 5H), 1.47-0.97 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 146.55, 142.06, 141.13, 134.43, 127.26, 126.47, 124.83, 123.80, 122.65, 117.89, 112.23, 57.12, 34.36, 25.66, 24.87.

HRMS (ESI): m/z 337.1670 (M+H)⁺; calc. for C₁₉H₂₁N₄O₂: 337.1665.

62 MLB133-648C N-cyclohexyl-2-isobutylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.08-7.95 (m, 1H), 7.50-7.36 (m, 1H), 7.03 (ddd, J=1.2, 6.7, 9.0, 1H), 6.70 (td, J=0.9, 6.7, 1H), 3.00-2.69 (m, 2H), 2.58 (d, J=7.1, 2H), 2.20 (dt, J=6.8, 13.4, 1H), 2.04-1.49 (m, 5H), 1.38-1.07 (m, 5H), 0.95 (d, J=6.6, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 141.29, 138.72, 125.17, 122.65, 122.38, 116.83, 110.81, 57.21, 36.67, 34.34, 28.88, 25.83, 24.92, 22.74.

HRMS (ESI): m/z 272.2105 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

63 MLB133-649B 4-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)phenol

¹H NMR (200 MHz, DMSO-d₆) δ 9.41 (s, 1H), 8.26 (d, J=6.9, 1H), 8.03 (d, J=8.6, 2H), 7.41 (d, J=8.9, 1H), 7.28-7.01 (m, 1H), 6.83 (t, J=7.3, 3H), 4.60 (d, J=5.5, 1 H), 3.45-3.38 (m, 1H), 3.00-2.65 (m, 1H), 2.01-1.40 (m, 5H), 1.40-0.85 (m, 5H).

¹³C NMR (50 MHz, DMSO-d₆) δ 154.73, 138.53, 133.82, 126.11, 123.79, 122.44, 121.29, 121.20, 114.42, 113.20, 109.01, 54.45, 31.83, 23.77, 22.78.

HRMS (ESI): m/z 308.1754 (M+H)⁺; calc. for C₁₉H₂₂N₃O: 308.1763.

64 MLB133-650A 2-tert-butyl-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.08 (dt, J=1.0, 6.9, 1H), 7.47 (d, J=9.0, 1H), 7.04 (ddd, J=1.3, 6.6, 8.9, 1H), 6.69 (td, J=0.9, 6.7, 1H), 3.17-2.71 (m, 2H), 2.06-1.51 (m, 6H), 1.47 (s, 9H), 1.40-1.02 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 140.10, 138.20, 123.62, 122.89, 116.56, 111.17, 109.72, 58.68, 34.13, 33.19, 30.66, 25.82, 25.05.

HRMS (ESI): m/z 272.2102 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

65 MLB133-650B N-(4-(3,4-dichlorophenoxy)butyl)-2-(furan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.88 (d, J=6.9, 1H), 7.50-7.25 (m, 2H), 7.15 (d, J=8.9, 1H), 6.98 (ddd, J=1.0, 6.7, 8.2, 1H), 6.83 (d, J=2.9, 1H), 6.79-6.72 (m, 1H), 6.70-6.50 (m, 2H), 6.47-6.24 (m, 1H), 3.79 (dd, J=7.6, 13.5, 2H), 3.59 (d, J=6.1, 1H), 2.98 (dd, J=6.4, 12.9, 2H), 1.88-1.31 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 157.76, 150.15, 141.52, 141.32, 132.52, 130.38, 129.19, 127.45, 126.16, 123.57, 122.13, 117.09, 116.14, 115.54, 114.26, 111.51, 106.26, 68.07, 48.10, 26.99, 26.46.

HRMS (ESI): m/z 416.0902 (M+H)⁺; calc. for C₂₁H₂₀N₃O₂Cl₂: 416.0933.

66 MLB133-650C N-(4-(3,4-dichlorophenoxy)butyl)-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.88 (dt, J=1.0, 6.8, 1H), 7.37 (br dt, J=9.0, 1H), 7.16 (d, J=8.9, 1H), 6.95 (dd, J=1.2, 6.7, 1H), 6.90 (dd, J=1.3, 6.8, 1H), 6.85 (d, J=2.9, 1 H), 6.71-6.49 (m, 1H), 3.82 (t, J=6.0, 2H), 3.20-2.99 (m, 1H), 2.92 (d, J=6.1, 3H), 1.89-1.44 (m, 4H), 1.27 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 157.76, 144.16, 141.06, 132.51, 129.16, 128.99, 123.96, 122.57, 121.87, 120.40, 116.86, 115.52, 114.26, 110.86, 68.08, 48.68, 27.25, 26.51, 26.25, 22.64.

HRMS (ESI): m/z 392.1259 (M+H)⁺; calc. for C₂₀H₂₄N₃OCl₂: 392.1296.

67 MLB133-650D N-(4-chlorobenzyl)-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.96 (d, J=6.8, 2H), 7.52 (d, J=9.0, 2H), 7.18-6.99 (m, 2H), 6.73 (t, J=6.7, 2H), 4.03 (s, 2H), 3.39-3.07 (m, 1H), 3.07-2.81 (m, 1H), 1.23 (d, J=6.9, 6H).

¹³C NMR (101 MHz, CDCl₃) δ 144.68, 141.38, 137.86, 133.42, 129.58, 128.75, 123.52, 123.24, 122.00, 117.17, 111.34, 52.60, 26.43, 22.69.

HRMS (ESI): m/z 300.1241 (M+H)⁺; calc. for C₁₇H₁₉N₃Cl: 300.1268.

68 MLB133-653A 2-(5-chlorofuran-2-yl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.98 (dt, J=1.1, 6.8, 1H), 7.47-7.34 (m, 1H), 7.04 (ddd, J=1.3, 6.7, 9.1, 1H), 6.76 (d, J=3.4, 1H), 6.69 (td, J=1.0, 6.8, 1H), 6.21 (d, J=3.4, 1H), 3.42 (d, J=6.6, 1H), 3.07-2.73 (m, 1H), 2.01-1.41 (m, 5H), 1.41-0.99 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 149.97, 141.83, 135.16, 127.34, 125.70, 124.15, 122.79, 117.22, 111.66, 108.25, 108.04, 57.38, 34.18, 25.76, 24.95.

HRMS (ESI): m/z 316.1195 (M+H)⁺; calc. for C₁₇H₁₉N₃OCl: 316.1217.

69 MLB133-653C N-cyclohexyl-2-(5-ethylthiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl3) δ 8.07 (dt, J=1.1, 6.9, 1H), 7.50 (d, J=9.0, 1H), 7.41 (d, J=3.6, 1H), 7.10 (ddd, J=1.3, 6.6, 9.0, 1H), 6.92-6.79 (m, 1H), 6.79-6.66 (m, 1H), 3.27-2.97 (m, 2H), 2.90 (dd, J=7.6, 15.1, 2H), 2.09-1.51 (m, 5H), 1.36 (t, J=7.5, 4H), 1.30-1.00 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 147.81, 140.51, 125.43, 125.06, 124.05, 123.45, 122.97, 116.09, 112.42, 57.03, 34.26, 25.74, 24.92, 23.51, 15.86.

HRMS (ESI): m/z 326.1695 (M+H)⁺; calc. for C₁₉H₂₄N₃S: 326.1691.

70 MLB133-654C₄-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)-2-methoxyphenol

¹H NMR (200 MHz, DMSO-d₆) δ 8.98 (s, 1H), 8.30 (d, 1H), 7.80 (s, 1H), 7.65 (d, 1H), 7.45 (d, 1H), 7.15 (t, 1H), 6.95-6.75 (m, 2H), 4.70 (d, 1H), 3.85 (s, 3H), 3.00-2.80 (m, 1H), 1.85-0.95 (m, 10H).

¹³C NMR (50 MHz, DMSO-d₆) δ 147.31, 145.71, 140.23, 135.31, 126.14, 124.33, 123.28, 123.08, 119.41, 116.30, 115.33, 110.96, 110.62, 56.21, 55.49, 33.55, 25.44, 24.43.

HRMS (ESI): m/z 338.1872 (M+H)⁺; calc. for C₂₀H₂₄N₃O₂: 338.1869.

71 MLB133-654A 5-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)-2-methoxyphenol

¹H NMR (200 MHz, CDCl₃-CD₃OD) δ 8.04 (d, 1H), 7.50-7.25 (m, 3H), 7.15-7.00 (m, 1H), 6.85 (d, 1H), 6.75-6.65 (m, 1H), 3.83 (s, 3H), 3.75-3.45 (m, 1H), 2.95-2.75 (m, 1H), 1.85-0.90 (m, 10H).

¹³C NMR (50 MHz, CDCl₃-DMSO-d₆) δ 147.18, 145.94, 140.35, 134.58, 125.63, 125.20, 124.38, 122.77, 118.47, 115.46, 113.79, 112.21, 111.22, 56.50, 55.59, 33.78, 25.46, 24.61.

HRMS (ESI): m/z 338.1873 (M+H)⁺; calc. for C₂₀H₂₄N₃O₂: 338.1869.

72 MLB133-654B N-cyclohexyl-2-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl3) δ 8.12 (d, J=6.9, 1H), 7.56 (d, J=8.9, 1H), 7.28 (d, J=4.3, 1H), 7.20-7.06 (m, 1H), 6.96 (d, J=5.1, 1H), 6.80 (td, J=0.7, 6.8, 1H), 3.46-3.04 (m, 1H), 3.04-2.76 (m, 1H), 2.47 (s, 3H), 2.02-1.43 (m, 5H), 1.36-0.94 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.26, 135.92, 131.79, 130.54, 129.38, 125.91, 124.12, 123.58, 122.66, 117.33, 111.51, 56.75, 33.92, 25.73, 24.74, 15.24.

HRMS (ESI): m/z 312.1534 (M+H)⁺; calc. for C₁₈H₂₂N₃S: 312.1534.

73 DG 402-49647 N-cyclohexyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.22 (d, J=8.2, 2H), 8.08 (dt, J=1.0, 6.0, 1H), 7.68 (d, J=8.3, 2H), 7.60-7.45 (m, 1H), 7.15 (ddd, J=1.2, 6.7, 9.0, 1H), 6.80 (td, J=1.0, 6.7, 1H), 3.29-2.67 (m, 2H), 1.96-1.42 (m, 5H), 1.42-0.91 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.75, 138.01, 135.14, 128.46, 126.91, 125.59, 125.31 (dd, J=3.8, 7.6), 124.45, 124.34, 122.64, 117.57, 111.84, 56.94, 34.22, 25.65, 24.81.

HRMS (ESI): m/z 360.1683 (M+H)⁺; calc. for C₂₀H₂₁N₃F₃: 360.1688.

74 DG 402-49648 2-(6-chloro-2-fluoro-3-methylphenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.14 (d, J=6.9, 1H), 7.57 (d, J=9.1, 1H), 7.26-7.05 (m, 3H), 6.82 (dd, J=3.8, 9.7, 1H), 3.02 (s, 1H), 2.82-2.60 (m, 1H), 2.31 (d, J=2.1, 3H), 1.75 (d, J=11.7, 2H), 1.65-1.54 (m, 2H), 1.54-1.40 (m, 1H), 1.22-0.87 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 160.71, 158.24, 141.67, 132.21, 131.55, 131.49, 127.21, 124.60, 124.56, 123.95, 123.77, 123.62, 122.76, 117.77, 111.56, 56.31, 33.76, 25.60, 24.61, 14.54.

HRMS (ESI): m/z 358.1481 (M+H)⁺; calc. for C₂₀H₂₂N₃ClF: 358.1486.

75 DG 402-49649 2-(4-chloro-3-fluorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.06 (d, J=6.8, 1H), 7.97 (dd, J=1.9, 10.9, 1H), 7.91-7.77 (m, 1H), 7.52 (d, J=9.3, 1H), 7.44 (t, J=8.1, 1H), 7.23-7.08 (m, 1H), 6.81 (td, J=0.8, 6.8, 1H), 3.16-2.79 (m, 2H), 1.99-1.42 (m, 6H), 1.42-0.90 (m, 7H).

¹³C NMR (50 MHz, CDCl₃) δ 160.56, 155.65, 141.62, 130.43, 125.07, 124.50, 123.14, 123.07, 122.58, 117.46, 115.11, 114.66, 111.96, 56.91, 34.24, 25.65, 24.83.

HRMS (ESI): m/z 344.1323 (M+H)⁺; calc. for C₁₉H₂₀N₃FCl: 344.1330.

76 DG 402-49650 2-(3-bromophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.35-8.21 (m, 1H), 8.15-8.04 (m, 1H), 8.04-7.90 (m, 1H), 7.61-7.47 (m, 1H), 7.43 (ddd, J=1.1, 1.9, 7.9, 1H), 7.29 (dd, J=5.4, 10.3, 1H), 7.13 (ddd, J=1.3, 6.7, 9.0, 1H), 6.79 (td, J=1.1, 6.8, 1H), 3.29-2.66 (m, 2H), 1.69 (M, 6H), 1.41-0.74 (m, 7H).

¹³C NMR (50 MHz, CDCl₃) δ 141.62, 136.60, 131.01, 130.03, 129.98, 129.89, 125.34, 124.13, 122.69, 122.63, 117.46, 111.72, 56.97, 34.25, 25.70, 24.82.

HRMS (ESI): m/z 370.0911 (M+H)⁺; calc. for C₁₉H₂₁N₃Br: 370.0919.

77 DG 402-49653 2-(4-bromophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.09-8.00 (m, 1H), 7.94 (d, J=8.6, 2H), 7.58-7.43 (m, 3H), 7.10 (ddd, J=1.3, 6.7, 9.0, 1H), 6.75 (td, J=1.1, 6.8, 1H), 3.01 (s, 2H), 1.93-1.39 (m, 5H), 1.16 (s, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.57, 135.62, 133.46, 131.43, 128.49, 124.83, 123.98, 122.55, 121.09, 117.33, 111.58, 56.77, 34.32, 25.66, 24.76.

HRMS (ESI): m/z 370.0926 (M+H)⁺; calc. for C₁₉H₂₁N₃Br: 370.0919.

78 DG 402-49655 2-(2-chlorophenyl)-N-(pentan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.26-8.03 (m, 1H), 7.77-7.61 (m, 1H), 7.61-7.50 (m, 1H), 7.50-7.41 (m, 1H), 7.41-7.21 (m, 2H), 7.12 (ddd, J=1.1, 6.7, 8.9, 1H), 6.78 (td, J=0.7, 6.7, 1H), 3.33-3.03 (m, 1H), 3.03-2.74 (m, 1H), 1.44-0.99 (m, 4H), 0.84 (d, J=6.3, 3H), 0.75 (dd, J=6.2, 7.4, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 141.51, 134.02, 132.58, 132.41, 129.29, 129.23, 128.97, 126.73, 123.51, 123.37, 122.63, 117.43, 111.41, 53.14, 39.54, 20.79, 18.85, 13.93.

HRMS (ESI): m/z 314.1402 (M+H)⁺; calc. for C₁₈H₂₁N₃Cl: 314.1424.

79 DG 402-49657 2-isopropyl-N-(pentan-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.12-7.92 (m, 1H), 7.59-7.40 (m, 1H), 7.05 (ddd, J=1.2, 6.7, 8.9, 1H), 6.71 (dd, J=0.8, 13.6, 1H), 3.25-2.98 (m, 2H), 2.95-2.56 (m, 1H), 1.63-1.40 (m, 3H), 1.37 (dd, J=2.9, 6.9, 6H), 1.06 (d, J=6.3, 2H), 0.93 (dd, J=5.5, 8.4, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 144.92, 141.51, 123.23, 122.69, 122.36, 117.07, 110.92, 53.66, 40.03, 26.24, 22.73, 21.01, 19.45, 14.24.

HRMS (ESI): m/z 246.1967 (M+H)⁺; calc. for C₁₅H₂₄N₃: 246.1970.

80 DG 402-49667 6,8-dichloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.13 (d, J=1.8, 1H), 7.75-7.64 (m, 1H), 7.52-7.42 (m, 2H), 7.42-7.29 (m, 4H), 7.24 (d, J=1.8, 1H), 3.29 (s, 1H), 2.66 (dd, J=7.7, 11.3, 1 H), 2.01-0.74 (m, 29H).

¹³C NMR (101 MHz, CDCl₃) δ 137.08, 133.13, 132.79, 132.67, 129.64, 129.60, 129.40, 128.19, 127.05, 123.79, 123.63, 119.68, 119.25, 67.07, 56.46, 33.79, 25.53, 24.49.

HRMS (ESI): m/z 394.0643 (M+H)⁺; calc. for C₁₉H₁₉N₃Cl₃: 394.0645.

81 DG 402-49663 2-(2-chlorophenyl)-N-cyclohexyl-6-fluoroimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.13 (d, J=1.8, 1H), 7.71-7.67 (m, 1H), 7.48-7.44 (m, 1H), 7.38-7.33 (m, 2H), 7.24 (d, J=1.8, 1H), 3.33 (d, J=29.8, 1H), 2.66 (s, 1H), 1.77-1.60 (m, 3H), 1.51 (dd, J=14.4, 43.3, 2H), 1.12-0.97 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 154.41, 152.06, 139.17, 136.70, 133.59, 132.41, 129.50, 129.33, 127.59, 127.57, 127.01, 118.12, 118.03, 115.96, 115.70, 109.51, 109.10, 56.28, 33.81, 25.55, 24.55.

HRMS (ESI): m/z 344.1299 (M+H)⁺; calc. for C₁₉H₂₀N₃ClF: 344.1330.

82 DG 402-49665 6-chloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.25-8.11 (m, 1H), 7.75-7.56 (m, 1H), 7.55-7.39 (m, 2H), 7.39-7.25 (m, 2H), 7.10 (ddd, J=1.2, 1.9, 9.5, 1H), 3.27 (d, J=6.8, 1H), 2.80-2.46 (m, 1H), 1.82-1.34 (m, 5H), 1.23-0.76 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 139.84, 136.39, 133.58, 132.56, 132.38, 129.44, 129.27, 126.88, 126.72, 124.94, 120.67, 120.08, 117.96, 56.36, 33.79, 25.58, 24.52.

HRMS (ESI): m/z 360.1019 (M+H)⁺; calc. for C₁₉H₂₀N₃Cl₂: 360.1034.

83 DG 402-49672 N-cyclopentyl-2-(2,4-dichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.16 (dt, J=1.2, 7.3, 1H), 7.63 (d, J=8.3, 1H), 7.58-7.41 (m, 2H), 7.42-7.30 (m, 1H), 7.15 (ddd, J=1.3, 6.7, 9.1, 1H), 6.82 (t, J=6.8, 1H), 3.33 (dt, J=5.7, 11.0, 1H), 3.14 (d, J=6.2, 1H), 1.75-1.37 (m, 6H), 1.37-1.04 (m, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 141.65, 134.28, 134.07, 133.27, 133.21, 132.75, 129.24, 127.27, 127.06, 123.97, 122.72, 117.53, 111.72, 59.36, 33.27, 23.29.

HRMS (ESI): m/z 346.0889 (M+H)⁺; calc. for C₁₈H₁₈N₃Cl₂: 346.0878.

84 DG 402-49673 2-(4-bromophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.05 (dt, J=1.1, 6.9, 1H), 8.00-7.89 (m, 2H), 7.61-7.44 (m, 3H), 7.12 (ddd, J=1.3, 6.7, 9.0, 1H), 6.76 (td, J=1.1, 6.8, 1H), 3.72-3.47 (m, 1H), 2.99 (d, J=3.9, 1H), 1.83-1.60 (m, 4H), 1.60-1.49 (m, 2H), 1.49-1.35 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.63, 135.83, 133.49, 131.45, 128.62, 125.49, 124.10, 122.47, 121.18, 117.44, 111.67, 59.06, 33.46, 23.57.

HRMS (ESI): m/z 356.0727 (M+H)⁺; calc. for C₁₈H₁₉N₃Br: 356.0762.

85 DG 402-49678 2-(3-bromophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.31-8.28 (m, 1H), 8.09 (d, J=6.8, 1H), 8.04-7.97 (m, 1H), 7.52 (dt, J=3.5, 7.8, 1H), 7.43 (ddd, J=0.9, 1.9, 7.9, 1H), 7.32-7.24 (m, 1H), 7.17-7.11 (m, 1H), 6.79 (td, J=0.8, 6.8, 1H), 3.66 (t, J=10.3, 1H), 3.01 (s, 1H), 1.88-1.65 (m, 4H), 1.65-1.53 (m, 2H), 1.53-1.39 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.71, 136.63, 135.41, 130.13, 130.10, 130.06, 129.94, 125.80, 125.52, 124.26, 122.70, 122.55, 117.61, 111.82, 59.24, 33.56, 23.61.

HRMS (ESI): m/z 356.0774 (M+H)⁺; calc. for C₁₈H₁₉N₃Br: 356.0762.

86 DG 402-49679 2-(4-chloro-3-fluorophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.05 (d, J=6.7, 1H), 7.96 (d, J=10.9, 1H), 7.85 (d, J=8.4, 1H), 7.51 (d, J=9.0, 1H), 7.42 (t, J=8.0, 1H), 7.20-7.07 (m, 1H), 6.79 (t, J=6.7, 1H), 3.88-3.40 (m, 1H), 2.97 (d, J=3.8, 1H), 1.87-1.62 (m, 4H), 1.62-1.52 (m, 2H), 1.52-1.35 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 159.39, 156.93, 141.73, 135.29, 135.22, 134.97, 130.38, 125.70, 124.44, 123.27, 123.23, 122.49, 119.51, 119.33, 117.62, 115.13, 114.90, 111.92, 59.12, 33.54, 23.61.

HRMS (ESI): m/z 330.1173 (M+H)⁺; calc. for C₁₈H₁₈N₃FCl: 330.1173.

87 DG 402-49680 2-(6-chloro-2-fluoro-3-methylphenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.23-8.08 (m, 1H), 7.56 (ddd, J=1.0, 1.9, 9.1, 1H), 7.23-7.06 (m, 3H), 6.87-6.72 (m, 1H), 3.54-3.27 (m, 1H), 2.96 (d, J=6.4, 1H), 2.39-2.21 (m, 3H), 1.72-1.51 (m, 4H), 1.51-1.37 (m, 2H), 1.37-1.16 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 160.78, 158.31, 141.64, 132.36, 132.32, 131.52, 131.45, 129.80, 127.90, 124.58, 124.54, 123.93, 123.74, 123.57, 122.61, 122.11, 121.92, 117.83, 111.52, 59.33, 33.16, 23.24, 14.48, 14.44.

HRMS (ESI): m/z 344.1328 (M+H)⁺; calc. for C₁₉H₂₀N₃FCl: 344.1330.

88 DG 402-49681 N-cyclopentyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.21 (d, J=8.0, 2H), 8.07 (d, J=6.9, 1H), 7.67 (d, J=7.9, 2H), 7.53 (d, J=9.1, 1H), 7.15 (dd, J=7.2, 8.5, 1H), 6.79 (t, J=6.8, 1H), 3.75-3.50 (m, J=9.6, 1H), 3.04 (d, J=3.2, 1H), 1.87-1.62 (m, 4H), 1.62-1.51 (m, 2H), 1.50-1.36 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.81, 138.09, 138.08, 135.39, 129.07, 128.75, 127.10, 126.25, 125.69, 125.33, 125.29, 125.25, 125.22, 124.40, 122.56, 117.66, 111.89, 59.20, 33.51, 23.57.

HRMS (ESI): m/z 346.1525 (M+H)⁺; calc. for C₁₉H₁₉N₃F₃: 346.1531.

89 DG 402-49686 N-cyclohexyl-2-(2,4-dichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.14 (ddd, J=0.9, 1.6, 6.9, 1H), 7.64-7.60 (m, 1H), 7.56-7.52 (m, 1H), 7.51-7.48 (m, 1H), 7.38-7.33 (m, 1H), 7.19-7.12 (m, 1H), 6.81 (tt, J=1.8, 9.2, 1H), 3.19 (d, J=6.0, 1H), 2.67 (dd, J=3.8, 9.0, 1H), 1.65 (t, J=11.2, 2H), 1.59 (dd, J=4.6, 8.9, 2H), 1.53-1.42 (m, 1H), 1.17-0.92 (m, 6H).

¹³C NMR (101 MHz, CDCl₃) δ 141.75, 134.27, 134.14, 133.34, 133.14, 132.80, 129.29, 127.33, 126.44, 123.93, 122.89, 117.57, 111.70, 56.43, 33.89, 25.62, 24.58.

HRMS (ESI): m/z 360.1025 (M+H)⁺; calc. for C₁₉H₂₀N₃Cl₂: 360.1034.

90 DG 402-49688 N-(1-adamantyl)-2-(2-chlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.39-8.34 (m, 1H), 7.75-7.68 (m, 1H), 7.52 (ddd, J=5.0, 6.0, 11.0, 1H), 7.48-7.43 (m, 1H), 7.40-7.29 (m, 2H), 7.17-7.11 (m, 1H), 6.82-6.75 (m, 1H), 3.28-3.11 (m, 1H), 1.95-1.83 (m, 3H), 1.52 (d, J=12.2, 3H), 1.42 (t, J=10.7, 9H).

¹³C NMR (101 MHz, CDCl₃) δ 142.21, 137.82, 134.92, 132.85, 132.46, 129.45, 129.04, 126.94, 124.04, 123.94, 123.77, 117.36, 111.21, 55.83, 43.49, 36.17, 29.61.

HRMS (ESI): m/z 378.1731 (M+H)⁺; calc. for C₂₃H₂₅N₃Cl: 378.1737.

91 DG 402-49690 N-(1-adamantyl)-2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.30 (dt, J=7.3, 15.7, 1H), 7.50 (dt, J=6.1, 12.2, 1H), 7.16-7.07 (m, 1H), 6.80-6.70 (m, 1H), 6.63-6.56 (m, 1H), 4.17-3.98 (m, 1H), 2.60-2.40 (m, 3H), 1.98 (d, J=20.6, 2H), 1.82-1.70 (m, 5H), 1.62-1.47 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 168.66, 159.46, 142.39, 128.08, 126.54, 124.33, 124.13, 117.50, 111.52, 101.16, 57.60, 43.42, 36.20, 29.78, 12.20.

HRMS (ESI): m/z 349.2013 (M+H)⁺; calc. for C₂₁H₂₅N₄O: 349.2028.

92 DG 402-49683 N-cyclopentyl-2-(2,6-difluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.19-8.13 (m, 1H), 7.56 (t, J=10.7, 1H), 7.41-7.29 (m, 1H), 7.19-7.11 (m, 1H), 7.06-6.97 (m, 2H), 6.87-6.75 (m, 1H), 3.48-3.32 (m, 1H), 3.07 (d, J=6.1, 1H), 1.73-1.53 (m, 4H), 1.53-1.38 (m, 2H), 1.38-1.24 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 162.09, 162.02, 159.61, 159.54, 142.02, 129.83, 129.72, 129.62, 128.46, 126.59, 123.80, 122.64, 117.88, 111.75, 111.69, 111.66, 111.56, 111.49, 59.42, 33.23, 23.24.

HRMS (ESI): m/z 314.1462 (M+H)⁺; calc. for C₁₈H₁₈N₃F₂: 314.1469.

93 DG 402-49694 N-(1-adamantyl)-2-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.28 (dt, J=1.2, 7.0, 1H), 7.51 (dt, J=1.1, 9.1, 1H), 7.27 (d, J=4.8, 1H), 7.12 (ddd, J=1.3, 6.6, 9.0, 1H), 6.93 (d, J=5.1, 1H), 6.76 (td, J=1.1, 6.8, 1H), 3.01 (s, 1H), 2.36 (s, 3H), 1.94 (s, 3H), 1.67-1.34 (m, 12H).

¹³C NMR (101 MHz, CDCl₃) δ 142.08, 135.20, 131.03, 130.16, 127.25, 124.57, 123.81, 123.58, 120.05, 117.31, 111.16, 56.25, 43.44, 36.19, 29.68, 15.17.

HRMS (ESI): m/z 364.1836 (M+H)⁺; calc. for C₂₂H₂₆N₃S: 364.1847.

94 DG 402-49700 2-(2-chlorophenyl)-N-(1-adamantyl)imidazo[2,1-a]isoquinolin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.66 (ddd, J=6.1, 6.6, 12.7, 1H), 8.18 (d, J=7.4, 1H), 7.78 (dd, J=1.8, 7.6, 1H), 7.73-7.67 (m, 1H), 7.62-7.50 (m, 2H), 7.48-7.44 (m, 1H), 7.42-7.36 (m, 1H), 7.36-7.29 (m, 1H), 7.05 (t, J=5.0, 1H), 3.23 (s, 1H), 1.90 (s, 3H), 1.66 (d, J=2.9, 3H), 1.51 (s, 2H), 1.46 (d, J=2.4, 8H).

¹³C NMR (101 MHz, CDCl₃) δ 139.64, 135.61, 134.88, 132.95, 132.50, 129.60, 129.57, 129.39, 128.86, 128.28, 127.80, 127.76, 127.00, 126.76, 123.88, 122.79, 121.30, 111.80, 55.63, 43.50, 36.12, 29.58.

HRMS (ESI): m/z 428.1896 (M+H)⁺; calc. for C₂₇H₂₇N₃Cl: 428.1894.

95 DG 402-49702 6-bromo-2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.71-7.55 (m, 1H), 7.55-7.42 (m, 1H), 7.42-7.29 (m, 2H), 7.25 (d, J=4.3, 2H), 3.18 (s, 3H), 2.55 (s, 1H), 1.53 (d, J=17.9, 5H), 1.16-0.65 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 142.05, 138.18, 137.93, 135.11, 134.05, 132.69, 132.49, 129.40, 129.23, 128.26, 126.90, 116.25, 109.91, 58.69, 33.04, 25.68, 24.68, 17.94.

HRMS (ESI): m/z 418.0676 (M+H)⁺; calc. for C₂₀H₂₂N₃ClBr: 418.0686.

96 DG 402-49704 2-(2-chlorophenyl)-3-(cyclohexylamino)imidazo[1,2-a]pyridine-6-carbonitrile

¹H NMR (400 MHz, CDCl₃) δ 8.65-8.55 (m, 1H), 7.68-7.63 (m, 1H), 7.61 (ddd, J=0.9, 3.4, 9.3, 1H), 7.53-7.46 (m, 1H), 7.43-7.32 (m, 2H), 7.27-7.19 (m, 1H), 3.53-3.13 (m, 1H), 2.86-2.55 (m, 1H), 1.60 (dd, J=23.5, 47.2, 5H), 1.20-0.95 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 140.47, 137.48, 132.83, 132.57, 132.30, 129.76, 129.62, 129.36, 127.41, 127.07, 123.24, 118.50, 117.05, 97.81, 56.58, 33.76, 25.44, 24.45.

HRMS (ESI): m/z 351.1361 (M+H)⁺; calc. for C₂₀H₂₀N₄Cl: 351.1376.

97 DG 402-49754 2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]quinolin-1-amine

¹H NMR (400 MHz, CDCl₃) δ 9.44 (dt, J=5.7, 11.5, 1H), 7.74 (dt, J=4.5, 9.0, 1H), 7.71-7.65 (m, 1H), 7.62-7.55 (m, 1H), 7.52-7.47 (m, 1H), 7.46-7.40 (m, 3H), 7.39-7.36 (m, 1H), 7.36-7.33 (m, 1H), 3.60-3.39 (m, 1H), 2.86-2.67 (m, 1H), 1.74 (dd, J=12.6, 18.3, 2H), 1.60-1.36 (m, 3H), 1.11-0.86 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 140.68, 134.79, 132.65, 131.29, 129.57, 129.44, 129.34, 129.05, 128.43, 127.66, 127.36, 127.01, 125.69, 124.42, 124.33, 117.52, 117.11, 56.59, 33.10, 25.58, 24.62.

HRMS (ESI): m/z 376.1576 (M+H)⁺; calc. for C₂₃H₂₃N₃Cl: 376.1581.

98 DG 402-49708 6-bromo-2-(2-chlorophenyl)-N-cyclohexyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.22-8.08 (m, 1H), 7.74-7.59 (m, 1H), 7.53-7.41 (m, 1H), 7.41-7.27 (m, 2H), 7.03 (dd, J=1.1, 1.8, 1H), 3.22 (d, J=6.9, 1H), 2.72-2.61 (m, 1H), 2.60 (s, 3H), 1.73-1.40 (m, 6H), 1.17-0.82 (m, 6H).

¹³C NMR (101 MHz, CDCl₃) δ 140.39, 135.51, 133.81, 132.77, 132.61, 129.42, 129.25, 128.52, 126.99, 126.84, 125.82, 120.85, 106.62, 56.38, 33.80, 25.59, 24.53, 16.43.

HRMS (ESI): m/z 418.0676 (M+H)⁺; calc. for C₂₀H₂₂N₃ClBr: 418.0686.

99 DG 402-49710 6-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl3) δ 8.33-8.21 (m, 1H), 7.70-7.56 (m, 1H), 7.52-7.45 (m, 1H), 7.45-7.40 (m, 1H), 7.40-7.29 (m, 2H), 7.20 (dd, J=1.9, 9.5, 1H), 3.25 (d, J=6.9, 1H), 2.66 (dd, J=3.4, 6.5, 1H), 1.75-1.62 (m, 2H), 1.61-1.52 (m, 2H), 1.52-1.39 (m, 1H), 1.18-0.86 (m, 5H).

¹³C NMR (101 MHz, CDCl3) δ 139.99, 136.23, 133.61, 132.62, 132.46, 129.52, 129.35, 127.06, 126.97, 126.62, 123.02, 118.30, 106.65, 56.41, 33.81, 25.58, 24.53.

HRMS (ESI): m/z 404.0512 (M+H)⁺; calc. for C₁₉H₂₀N₃ClBr: 404.0529.

100 DG 402-49692 N-(1-adamantyl)-2-octylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.30-8.09 (m, 1H), 7.43 (dt, J=1.1, 9.0, 1H), 7.04 (ddd, J=1.3, 6.6, 9.0, 1H), 6.69 (td, J=1.1, 6.8, 1H), 2.77-2.70 (m, 2H), 2.05 (d, J=8.4, 3H), 1.79 (dt, J=7.7, 15.7, 2H), 1.72 (d, J=2.5, 6H), 1.64 (d, J=12.3, 3H), 1.57 (d, J=12.3, 3H), 1.45-1.17 (m, 11H), 0.87 (t, J=6.9, 3H).

¹³C NMR (101 MHz, CDCl₃) δ 141.92, 141.67, 123.26, 122.92, 122.06, 116.66, 110.52, 55.48, 44.01, 36.27, 31.87, 29.91, 29.73, 29.54, 29.46, 29.25, 27.98, 22.65, 14.06.

HRMS (ESI): m/z 380.3053 (M+H)⁺; calc. for C₂₅H₃₈N₃: 380.3066.

101 DG 402-49675 2-(2-bromophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.17 (dt, J=1.1, 6.9, 1H), 7.64 (ddd, J=1.3, 4.4, 9.5, 2H), 7.59-7.49 (m, 1H), 7.40 (ddd, J=0.6, 1.2, 7.5, 1H), 7.27-7.20 (m, 1H), 7.18-7.08 (m, 1H), 6.80 (ddd, J=0.6, 1.0, 6.7, 1H), 3.46-3.27 (m, 1H), 3.21 (d, J=6.4, 1H), 1.68-1.48 (m, 4H), 1.48-1.35 (m, 2H), 1.35-1.13 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.31, 136.72, 136.11, 132.69, 132.53, 129.32, 127.29, 126.48, 123.65, 122.88, 122.68, 117.54, 111.55, 59.30, 33.16, 23.19.

HRMS (ESI): m/z 356.0768 (M+H)⁺; calc. for C₁₈H₁₉N₃Br: 356.0762.

102 DG 402-49682 N-cyclopentyl-2-(2,6-dichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.16 (d, J=6.9, 1H), 7.67-7.49 (m, 1H), 7.49-7.36 (m, 2H), 7.33-7.21 (m, 1H), 7.19-7.03 (m, 1H), 6.81 (dd, J=3.6, 10.3, 1H), 3.50-3.32 (m, 1H), 2.84 (d, J=6.0, 1H), 1.72-1.53 (m, 4H), 1.53-1.40 (m, 2H), 1.40-1.27 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.46, 136.35, 132.97, 129.88, 128.01, 127.38, 123.61, 122.70, 117.89, 111.60, 59.41, 33.29, 23.34.

HRMS (ESI): m/z 346.0877 (M+H)⁺; calc. for C₁₈H₁₈N₃Cl₂: 346.0878.

103 DG 402-49696 N-(1-adamantyl)-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.18 (dt, J=1.2, 6.9, 1H), 7.39 (dt, J=1.1, 9.0, 1H), 7.03 (ddt, J=1.2, 6.7, 9.0, 1H), 6.68 (td, J=1.1, 6.8, 1H), 2.77 (s, 1H), 2.19-1.93 (m, 4H), 1.77 (d, J=2.5, 6H), 1.61 (q, J=12.2, 6H), 1.13-1.03 (m, 2H), 0.99-0.91 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 142.47, 141.73, 122.88, 122.75, 122.49, 116.39, 110.46, 55.60, 43.98, 36.27, 29.73, 8.87, 8.18.

HRMS (ESI): m/z 308.2128 (M+H)⁺; calc. for C₂₀H₂₆N₃: 308.2127.

104 DG402-49748 5-chloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 7.63-7.56 (m, 1H), 7.49 (dddd, J=1.3, 1.8, 4.5, 5.0, 2H), 7.39-7.30 (m, 2H), 7.08-6.99 (m, 1H), 6.80-6.73 (m, 1H), 3.31 (d, J=6.8, 1H), 2.81 (s, 1H), 1.67 (d, J=12.5, 2H), 1.52 (s, 2H), 1.45 (s, 1H), 1.06 (t, J=10.4, 3H), 0.89 (d, J=10.1, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 143.62, 137.52, 133.65, 133.24, 132.59, 129.49, 129.25, 128.24, 126.67, 125.99, 123.55, 116.77, 114.06, 58.58, 32.78, 25.67, 24.50.

HRMS (ESI): m/z 360.1014 (M+H)⁺; calc. for C₁₉H₂₀N₃Cl₂: 360.1034.

105 DG 402-49758 2-(2-bromophenyl)-N-cyclohexylimidazo[2,1-a]isoquinolin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.66 (d, J=8.0, 1H), 7.99 (dd, J=1.3, 7.3, 1H), 7.75-7.63 (m, 3H), 7.63-7.56 (m, 1H), 7.56-7.48 (m, 1H), 7.42 (ddd, J=1.4, 4.5, 7.6, 1 H), 7.32-7.18 (m, 1H), 7.06 (d, J=7.3, 1H), 3.29 (d, J=6.9, 1H), 2.70 (s, 1H), 1.79-1.64 (m, 2H), 1.57 (s, 2H), 1.51-1.42 (m, 1H), 1.17-0.97 (m, 4H), 0.95-0.75 (m, 1H).

¹³C NMR (101 MHz, CDCl₃) δ 138.83, 136.11, 134.54, 132.88, 132.55, 129.39, 129.25, 127.85, 127.74, 127.62, 127.50, 126.87, 123.95, 123.13, 122.73, 120.43, 112.28, 56.86, 33.75, 25.62, 24.53.

HRMS (ESI): m/z 420.1063 (M+H)⁺; calc. for C₂₃H₂₃N₃Br: 420.1075.

106 SG389-832C N-cyclohexyl-2-(2,5-dichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.15 (d, J=7.1, 1H), 7.69 (d, J=2.5, 1H), 7.52 (d, J=9.1, 1H), 7.46-7.06 (m, 5H), 6.84 (d, J=6.7, 1H), 2.25-2.07 (m, 5H), 1.83-1.43 (m, 12H), 1.41-0.96 (m, 25H), 0.96-0.73 (m, 16H).

¹³C NMR (50 MHz, CDCl₃) δ 138.21, 132.79, 132.26, 130.77, 130.64, 130.58, 129.45, 129.10, 128.52, 124.09, 122.92, 117.54, 111.80, 56.52, 33.93, 31.59, 24.61.

HRMS (ESI): m/z 360.1037 (M+H)⁺; calc. for C₁₉H₂₀N₃Cl₂: 360.1034.

107 SG389-834H N-cyclopentyl-2-(2,4-difluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.15 (dt, J=1.0, 6.9, 1H), 7.60 (d, J=8.3, 1H), 7.51 (dt, J=0.9, 9.0, 1H), 7.48 (d, J=2.1, 1H), 7.34-7.30 (m, 1H), 7.14 (ddd, J=1.2, 6.7, 9.0, 1H), 6.79 (td, J=0.9, 6.7, 1H), 3.39-3.27 (m, 1H), 3.20 (s, 1H), 1.68-1.48 (m, 4H), 1.48-1.34 (m, 2H), 1.34-1.17 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.30, 134.09, 133.50, 133.02, 132.97, 132.30, 129.01, 127.05, 126.87, 123.99, 122.53, 117.06, 111.62, 58.99, 32.94, 22.99.

HRMS (ESI): m/z 314.1473 (M+H)⁺; calc. for C₁₈H₁₈N₃F₂: 314.1469.

108 SG389-832A 2-(3-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.21-8.10 (m, 1H), 8.07 (d, J=6.9, 1H), 8.01-7.82 (m, 1H), 7.52 (d, J=9.1, 1H), 7.43-7.20 (m, 2H), 7.20-7.02 (m, 1H), 6.78 (t, J=6.8, 1 H), 3.20-2.75 (m, 2H), 1.99-1.42 (m, 6H), 1.42-0.92 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.55, 136.30, 135.18, 134.39, 129.55, 127.06, 127.02, 125.17, 124.86, 124.08, 122.60, 117.40, 111.66, 56.90, 34.19, 25.67, 24.78.

HRMS (ESI): m/z 326.1423 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

109 SG389-832D N-cyclohexyl-2-(2,6-dichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.15 (d, J=6.9, 1H), 7.56 (d, J=9.1, 1H), 7.48-7.35 (m, 2H), 7.28 (dd, J=6.6, 8.8, 1H), 7.21-7.02 (m, 1H), 6.81 (td, J=0.7, 6.7, 1H), 3.03-2.55 (m, 2H), 1.93-1.40 (m, 8H), 1.39-0.96 (m, 14H), 0.96-0.65 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 141.53, 136.31, 133.06, 129.85, 128.90, 128.00, 126.72, 123.56, 122.85, 117.83, 111.55, 56.58, 33.84, 25.69, 24.60.

HRMS (ESI): m/z 360.1042 (M+H)⁺; calc. for C₁₉H₂₀N₃Cl₂: 360.1034.

110 SG389-832E N-cyclohexyl-2-(2,6-difluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.13 (dt, J=1.2, 6.9, 1H), 7.57 (dt, J=1.1, 9.1, 1H), 7.34 (tt, J=6.4, 8.3, 1H), 7.14 (ddd, J=1.3, 6.6, 9.1, 1H), 7.03 (t, J=8.1, 2H), 6.80 (td, J=1.1, 6.8, 1H), 3.12 (s, 1H), 2.71 (s, 1H), 1.84-1.66 (m, 2H), 1.66-1.54 (m, 2H), 1.54-1.42 (m, 1H), 1.21-0.92 (m, 6H).

¹³C NMR (101 MHz, CDCl₃) δ 161.92, 161.85, 159.44, 159.37, 141.97, 129.75, 129.64, 129.54, 127.74, 126.45, 123.75, 122.71, 117.69, 111.72, 111.59, 111.46, 56.40, 33.87, 25.53, 24.64.

HRMS (ESI): m/z 328.1630 (M+H)⁺; calc. for C₁₉H₂₀N₃F₂: 328.1625.

111 DG 402-49756 N-cyclohexyl-2-(2-fluorophenyl)imidazo[2,1-a]isoquinolin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.66 (ddd, J=0.7, 1.3, 2.6, 1H), 8.04-7.94 (m, 2H), 7.70 (dd, J=0.9, 8.0, 1H), 7.66-7.57 (m, 1H), 7.54 (ddd, J=1.4, 7.2, 7.7, 1H), 7.40-7.27 (m, 2H), 7.20-7.12 (m, 1H), 7.05 (d, J=7.2, 1H), 3.49 (s, 1H), 2.72 (s, 1H), 1.78 (s, 2H), 1.62 (s, 2H), 1.51 (s, 1H), 1.10 (d, J=7.7, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 160.62, 158.21, 139.52, 131.50, 129.37, 128.88, 128.79, 127.86, 127.82, 126.90, 124.76, 123.94, 122.75, 120.52, 119.88, 115.68, 115.45, 112.25, 57.26, 33.96, 25.63, 24.83.

HRMS (ESI): m/z 360.1857 (M+H)⁺; calc. for C₂₃H₂₃N₃F: 360.1876.

112 SG389-816A N-(2-chloro-6-methylphenyl)-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.91 (d, J=6.8, 1H), 7.46 (d, J=9.0, 1H), 7.25 (d, J=6.8, 1H), 7.17-7.00 (m, 1H), 6.93 (d, J=7.1, 1H), 6.77 (dd, J=6.7, 14.2, 2H), 5.87 (s, 1H), 2.85 (s, 1H), 1.79-1.49 (m, 3H), 1.16-0.85 (m, 2H), 0.85-0.54 (m, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 142.56, 141.29, 139.91, 130.63, 128.32, 127.15, 123.48, 123.38, 121.58, 121.34, 120.13, 116.68, 111.66, 18.16, 7.62, 7.17.

HRMS (ESI): m/z 298.1123 (M+H)⁺; calc. for C₁₇H₁₇N₃Cl: 298.111.

113 SG389-832B N-cyclohexyl-2-(2-fluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.15 (d, J=6.9, 1H), 7.92 (td, J=2.3, 7.6, 1H), 7.54 (d, J=9.1, 1H), 7.22 (m, 4H), 6.79 (t, J=6.7, 1H), 3.45 (t, J=7.8, 1H), 2.91-2.46 (m, 1H), 1.88-1.34 (m, 5H), 1.21-0.83 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.74, 131.58, 131.49, 129.15, 128.98, 124.60, 124.54, 123.65, 122.88, 117.38, 115.76, 115.29, 111.44, 56.65, 34.01, 25.66, 24.79.

HRMS (ESI): m/z 310.1724 (M+H)⁺; calc. for C₁₉H₂₁N₃F: 310.1720.

114 SG389-834A 2-(3-chlorophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.13 (t, J=1.9, 1H), 8.04 (dt, J=1.1, 6.9, 1H), 7.94 (dt, J=1.4, 7.7, 1H), 7.50 (dt, J=1.0, 9.0, 1H), 7.33 (t, J=7.8, 1H), 7.25 (ddd, J=1.1, 2.1, 8.0, 1H), 7.15-7.07 (m, 1H), 6.75 (td, J=1.1, 6.8, 1H), 3.70-3.52 (m, 1H), 3.03 (d, J=3.2, 1H), 1.84-1.61 (m, 4H), 1.59-1.49 (m, 2H), 1.49-1.32 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.48, 136.13, 135.21, 134.29, 129.53, 127.09, 126.98, 125.72, 124.90, 124.28, 122.49, 117.31, 111.74, 59.01, 33.40, 23.49.

HRMS (ESI): m/z 312.1273 (M+H)⁺; calc. for C₁₈H₁₉N₃Cl: 312.1268.

115 SG389-834C₂-(4-chlorophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.08 (dt, J=1.2, 6.9, 1H), 8.04-7.98 (m, 2H), 7.52 (dt, J=1.0, 9.1, 1H), 7.42-7.37 (m, 2H), 7.14 (ddd, J=1.3, 6.7, 9.0, 1H), 6.79 (td, J=1.1, 6.8, 1H), 3.62 (s, 1H), 3.02 (s, 1H), 1.83-1.62 (m, 4H), 1.62-1.50 (m, 2H), 1.50-1.38 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.49, 135.58, 133.05, 132.74, 128.58, 128.33, 125.47, 124.38, 122.54, 117.29, 111.85, 59.05, 33.45, 23.56.

HRMS (ESI): m/z 312.1273 (M+H)⁺; calc. for C₁₈H₁₉N₃Cl: 312.1268.

116 CW23836 2-(2-chlorophenyl)-3-(cyclohexylamino)imidazo[1,2-a]pyridine-5-carbonitrile

¹H NMR (400 MHz, CDCl₃) δ 7.80 (dd, J=0.9, 9.0, 1H), 7.62 (dt, J=3.1, 5.4, 1H), 7.54-7.47 (m, 1H), 7.45-7.34 (m, 3H), 7.17 (dd, J=7.1, 8.9, 1H), 3.33 (d, J=7.1, 1H), 2.79 (d, J=3.3, 1H), 1.73 (d, J=10.2, 2H), 1.55 (d, J=3.8, 3H), 1.44 (d, J=13.8, 1H), 1.04 (dd, J=10.2, 19.7, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 141.06, 138.44, 133.09, 132.37, 129.80, 129.66, 128.09, 127.08, 124.31, 124.30, 122.94, 121.90, 113.97, 108.02, 57.24, 32.67, 25.60, 24.54.

117 SG389-812 N-(3-chlorophenyl)-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.78 (d, J=6.8, 1H), 7.56 (d, J=9.0, 1H), 7.25-7.11 (m, 1H), 7.06 (t, J=8.0, 1H), 6.86-6.61 (m, 2H), 6.51 (t, J=2.0, 1H), 6.37 (dd, J=2.2, 8.1, 1H), 5.81 (s, 1H), 3.27-2.83 (m, 1H), 1.29 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 148.27, 146.94, 142.60, 135.34, 130.53, 124.27, 122.19, 119.44, 117.33, 116.27, 113.16, 111.83, 111.28, 26.71, 22.22.

HRMS (ESI): m/z 286.1118 (M+H)⁺; calc. for C₁₆H₁₇N₃Cl: 286.111.

118 SG389-834B 2-(2-chlorophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.23-8.13 (m, 1H), 7.76-7.62 (m, 1H), 7.62-7.42 (m, 2H), 7.42-7.23 (m, 2H), 7.15 (ddd, J=1.3, 6.8, 9.1, 1H), 6.81 (td, J=1.0, 6.8, 1H), 3.34 (dt, J=5.0, 10.2, 1H), 3.21 (d, J=6.4, 1H), 2.21-1.82 (m, 1H), 1.72-1.04 (m, 7H).

¹³C NMR (50 MHz, CDCl₃) δ 141.55, 134.01, 132.66, 132.57, 129.44, 129.11, 127.00, 126.87, 123.74, 122.71, 117.56, 111.60, 59.42, 33.24, 23.28.

HRMS (ESI): m/z 312.1270 (M+H)⁺; calc. for C₁₈H₁₉N₃Cl: 312.1268.

119 SG389-816B N-(2-chloro-6-methylphenyl)-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.02 (dd, J=1.1, 6.8, 1H), 7.56 (d, J=9.0, 1H), 7.26 (d, J=7.8, 1H), 7.20-6.99 (m, 1H), 6.93 (d, J=6.7, 1H), 6.88-6.63 (m, 2H), 5.77 (s, 1H), 2.85 (dt, J=6.9, 13.8, 1H), 1.61 (s, 3H), 1.23 (dd, J=7.3, 14.5, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 146.67, 141.52, 140.23, 130.59, 128.13, 127.27, 123.44, 123.32, 122.01, 121.38, 118.58, 117.02, 111.81, 26.15, 21.73 (br), 18.03.

HRMS (ESI): m/z 300.1271 (M+H)⁺; calc. for C₁₇H₁₉N₃Cl: 300.1268.

120 SG389-816C N-(2-chloro-6-methylphenyl)-2-ethylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.14-7.91 (m, 1H), 7.52 (d, J=9.0, 1H), 7.26 (d, J=6.1, 1H), 7.21-7.03 (m, 1H), 6.94 (d, J=7.1, 1H), 6.81 (t, J=7.6, 2H), 5.76 (s, 1H), 2.50 (dd, J=7.6, 15.1, 2H), 1.62 (s, 3H), 1.14 (t, J=7.6, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 142.86, 141.53, 140.10, 130.61, 128.49, 127.27, 123.58, 123.46, 122.01, 121.58, 119.58, 117.02, 111.86, 20.34, 18.11, 12.84.

HRMS (ESI): m/z 286.1117 (M+H)⁺; calc. for C₁₆H₁₇N₃Cl: 286.1111.

121 SG389-834G N-cyclopentyl-2-(2,5-dichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.16 (dt, J=1.2, 6.9, 1H), 7.67 (d, J=2.6, 1H), 7.49 (dt, J=1.1, 9.1, 1H), 7.39 (d, J=8.6, 1H), 7.29 (dd, J=2.6, 8.6, 1H), 7.17 (ddd, J=1.3, 6.7, 9.1, 1H), 6.82 (tt, J=3.2, 6.5, 1H), 3.37 (d, J=25.1, 1H), 3.18 (s, 1H), 2.02-1.88 (m, 1H), 1.70-1.50 (m, 4H), 1.50-1.37 (m, 2H), 1.37-1.19 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 141.47, 135.21, 132.65, 132.04, 130.71, 130.45, 129.10, 128.93, 128.48, 124.32, 122.70, 117.19, 111.87, 59.24, 33.10, 23.10.

HRMS (ESI): m/z 346.0878 (M+H)⁺; calc. for C₁₈H₁₈N₃Cl₂: 346.0878.

122 SG389-832F N-cyclohexyl-2-(2,4,5-trifluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.14 (dt, J=1.1, 6.9, 1H), 7.57 (dt, J=1.1, 9.1, 1H), 7.35 (tt, J=6.4, 8.4, 1H), 7.15 (ddd, J=1.3, 6.6, 9.1, 1H), 7.03 (t, J=8.1, 1H), 6.81 (td, J=1.1, 6.8, 1H), 3.11 (s, 1H), 2.67 (m, 1H), 1.75 (m, 2H), 1.69-1.56 (m, 2H), 1.56-1.38 (m, 1H), 1.07 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 161.95, 161.88, 159.48, 159.41, 142.03, 129.69, 123.82, 122.76, 117.76, 111.78, 111.65, 111.52, 56.46, 34.04, 25.58, 24.70.

HRMS (ESI): m/z 346.1534 (M+H)⁺; calc. for C₁₉H₁₉N₃F₃: 346.1531.

123 SG389-834E N-cyclopentyl-2-(2-fluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.15 (d, J=6.9, 1H), 7.92 (td, J=2.2, 7.5, 1H), 7.53 (d, J=9.0, 1H), 7.29 (ddd, J=4.8, 8.8, 13.0, 2H), 7.13 (dd, J=9.4, 16.2, 2H), 6.75 (t, J=6.3, 1H), 3.55-3.15 (m, 2H), 1.77-1.09 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 161.82, 156.95, 141.45, 131.43, 131.35, 129.31, 129.14, 124.53, 124.46, 124.17, 122.70, 116.93, 115.65, 115.18, 111.70, 59.30, 33.09, 23.16.

HRMS (ESI): m/z 296.1566 (M+H)⁺; calc. for C₁₈H₁₉N₃F: 296.1563.

124 SM60 N,2-dicyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.07-7.97 (m, 1H), 7.53-7.43 (m, 1H), 7.04 (ddd, J=1.2, 6.5, 8.9, 1H), 6.71 (td, J=0.8, 6.6, 1H), 3.02-2.59 (m, 2H), 2.03-1.51 (m, 13H), 1.51-1.00 (m, 8H).

¹³C NMR (50 MHz, CDCl3) δ 144.01, 141.36, 138.21, 122.68, 122.43, 116.98, 110.93, 57.21, 36.47, 34.28, 33.02, 26.91, 26.04, 25.86, 24.95.

HRMS (ESI): m/z 298.2261 (M+H)⁺; calc. for C₁₉H₂₈N₃: 298.2283.

125 SM2 N-cyclohexyl-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.13-7.92 (m, 2H), 7.52 (dt, J=1.0, 9.1, 1H), 7.22-6.97 (m, 2H), 6.77 (td, J=1.1, 6.8, 1H), 3.31-2.47 (m, 2H), 1.93-1.40 (m, 4H), 1.40-0.86 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 164.7, 160.0, 142.1, 131.3, 129.6, 129.4, 124.9, 124.0, 123.4, 117.9, 116.4, 115.7, 112.2, 57.3, 35.3, 26.1, 25.0.

HRMS (ESI): m/z 310.1721 (M+H)⁺; calc. for C₁₉H₂₁N₃F: 310.1720.

126 SM61 N,2-dicyclohexyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.89 (dd, J=0.9, 7.0, 1H), 6.83 (d, J=6.8, 1H), 6.61 (t, J=6.8, 1H), 3.01-2.65 (m, 2H), 2.57 (s, 3H), 2.05-1.52 (m, 15H), 1.52-1.32 (m, 4H), 1.32-1.02 (m, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 143.45, 138.22, 126.60, 123.69, 121.57, 120.35, 110.81, 57.34, 37.09, 34.29, 32.90, 26.95, 25.96, 25.89, 24.99, 16.93.

HRMS (ESI): m/z 312.2404 (M+H)⁺; calc. for C₂₀H₃₀N₃: 312.2440.

127 SM62 N,2-dicyclohexyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.89 (d, J=7.2, 1H), 7.23 (s, 1H), 6.54 (dd, J=1.3, 6.8, 1H), 2.98-2.55 (m, 2H), 2.35 (s, 3H), 1.96-1.66 (m, 10H), 1.66-1.48 (m, 3H), 1.48-1.30 (m, 3H), 1.30-1.00 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 137.08, 133.51, 128.81, 126.28, 121.76, 115.49, 113.53, 57.35, 36.49, 34.25, 33.00, 26.94, 26.06, 25.89, 24.96, 21.23.

HRMS (ESI): m/z 312.2409 (M+H)⁺; calc. for C₂₀H₃₀N₃: 312.2440.

128 SM63 N,2-dicyclohexyl-6-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.77 (s, 1H), 7.37 (d, J=9.1, 1H), 6.89 (dd, J=1.7, 9.1, 1H), 2.97-2.78 (m, 2H), 2.31 (s, 3H), 2.06-1.49 (m, 13H), 1.34 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 143.91, 140.49, 125.77, 123.03, 120.41, 120.11, 116.36, 57.13, 36.46, 34.26, 33.04, 26.94, 26.06, 25.88, 24.97, 18.38.

HRMS (ESI): m/z 312.2408 (M+H)⁺; calc. for C₂₀H₃₀N₃: 312.2440.

129 SM64 N,2-dicyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.32 (d, J=8.2, 1H), 7.07-6.74 (m, 1H), 6.34 (d, J=6.8, 1H), 2.88 (s, 3H), 2.70 (m, 2H), 2.00-1.53 (m, 13H), 1.52-0.98 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 146.00, 143.08, 135.88, 124.67, 122.94, 115.28, 112.64, 59.65, 36.23, 33.44, 32.87, 26.93, 25.96, 25.15, 19.76.

HRMS (ESI): m/z 312.2428 (M+H)⁺; calc. for C₂₀H₃₀N₃: 312.2440.

130 SM662-cyclohexyl-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.03 (dd, J=0.8, 6.7, 1H), 7.47 (dd, J=0.9, 9.0, 1H), 7.13-6.90 (m, 1H), 6.70 (t, J=6.7, 1H), 3.59 (m, 1H), 3.00-2.49 (m, 1H), 2.25-0.94 (m, 19H).

¹³C NMR (50 MHz, CDCl₃) δ 144.25, 141.35, 123.99, 122.73, 122.30, 117.01, 110.94, 59.92, 36.53, 33.53, 33.00, 26.91, 26.03, 23.60.

HRMS (ESI): m/z 284.2106 (M+H)⁺; calc. for C₁₈H₂₆N₃: 284.2127.

131 SM672-cyclohexyl-N-cyclopentyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.91 (d, J=6.3, 1H), 6.84 (d, J=6.8, 1H), 6.62 (t, J=6.7, 1H), 3.59 (m, 1H), 2.99-2.64 (m, 1H), 2.57 (s, 3H), 2.16-0.77 (m, 19H).

¹³C NMR (50 MHz, CDCl₃) δ 143.58, 126.58, 124.38, 123.88, 121.70, 120.19, 110.86, 60.00, 37.06, 33.52, 32.84, 26.92, 25.94, 23.60, 16.88.

HRMS (ESI): m/z 298.2234 (M+H)⁺; calc. for C₁₉H₂₈N₃: 298.2283.

132 SM682-cyclohexyl-N-cyclopentyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.92 (d, J=6.5, 1H), 7.26 (d, J=6.4, 1H), 6.57 (t, J=6.6, 1H), 2.88-2.61 (m, 1H), 2.29 (s, 3H), 2.08-1.31 (m, 12H), 1.31-1.00 (m, 7H).

¹³C NMR (50 MHz, CDCl3) δ 144.2, 142.6, 134.4, 123.3, 122.6, 116.1, 115.3, 60.8, 37.4, 35.38, 34.3, 27.2, 26.5, 25.7, 21.6.

HRMS (ESI): m/z 298.2247 (M+H)⁺; calc. for C₁₉H₂₈N₃: 298.2283.

133 SM692-cyclohexyl-N-cyclopentyl-6-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.81 (s, 1H), 7.42 (d, J=9.1, 1H), 6.92 (d, J=9.3, 1H), 3.69-3.48 (m, 1H), 2.91-2.58 (m, 1H), 2.32 (s, 3H), 2.00-0.98 (m, 19H).

¹³C NMR (50 MHz, CDCl₃) δ 143.87, 140.64, 139.16, 138.19, 125.96, 123.66, 120.80, 119.99, 116.31, 114.35, 59.76, 36.47, 33.48, 32.97, 29.29, 26.92, 26.02, 25.64, 23.60, 18.33.

HRMS (ESI): m/z 298.2250 (M+H)⁺; calc. for C₁₉H₂₈N₃: 298.2283.

134 SM702-cyclohexyl-N-cyclopentyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.36 (t, J=7.4, 1H), 7.03-6.78 (m, 1H), 6.35 (t, J=7.3, 1H), 4.01-3.24 (m, 4H), 2.92 (s, 2H), 2.71-2.50 (m, 2H), 2.50-2.07 (m, 4H), 2.04-0.96 (m, 27H).

¹³C NMR (50 MHz, CDCl₃) δ 145.55, 136.00, 125.97, 123.29, 122.79, 122.74, 115.31, 115.22, 115.09, 112.86, 112.52, 112.28, 62.69, 36.24, 32.94, 32.89, 26.99, 26.87, 26.01, 23.71, 19.74.

HRMS (ESI): m/z 298.2251 (M+H)⁺; calc. for C₁₉H₂₈N₃: 298.2283.

135 SM52 N-cyclohexyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.06-7.95 (m, 1H), 7.58-7.44 (m, 1H), 7.44-7.11 (m, 5H), 7.05 (ddd, J=1.2, 6.7, 8.8, 1H), 6.71 (t, J=6.7, 1H), 4.33 (q, J=7.1, 1H), 2.87-2.28 (m, 2H), 1.98-1.43 (m, 8H), 1.43-0.78 (m, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 145.64, 142.00, 141.09, 128.41, 128.35, 127.97, 127.43, 126.01, 122.77, 122.43, 117.07, 111.08, 57.20, 37.99, 34.13, 25.75, 24.90, 24.80, 21.71.

HRMS (ESI): m/z 320.2073 (M+H)⁺; calc. for C₂₁H₂₆N₃: 320.2127.

136 SM53 N-cyclohexyl-8-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.98-7.83 (m, 1H), 7.62-7.10 (m, 5H), 6.95-6.83 (m, 1H), 6.64 (t, J=6.8, 1H), 4.42 (q, J=7.1, 1H), 2.65 (s, 3H), 2.52-2.23 (m, 1H), 1.84 (d, J=7.2, 3H), 1.77-1.47 (m, 5H), 1.36-0.90 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 145.60, 141.51, 141.35, 128.28, 127.57, 126.75, 125.95, 124.79, 121.56, 120.39, 110.91, 57.38, 38.31, 34.02, 25.79, 24.92, 21.71, 16.74.

HRMS (ESI): m/z 334.2242 (M+H)⁺; calc. for C₂₂H₂₈N₃: 334.2283.

137 SM54 N-cyclohexyl-7-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.92 (m, 1H), 7.42-7.14 (m, 6H), 6.65 (dd, 1H), 4.32 (q, 1H), 2.78 (s, 1H), 2.31 (s, 1H), 1.83 (d, 3H), 1.88-1.54 (m, 5H), 1.29-1.04 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 146.8, 142.0, 134.7, 129.3, 128.4, 128.0, 127.5, 126.8, 123.1, 121.8, 116.7, 115.6, 59.8, 39.5, 34.8, 26.6, 25.3, 23.9, 22.2.

HRMS (ESI): m/z 334.2255 (M+H)⁺; calc. for C₂₂H₂₈N₃: 334.2283.

138 SM55 N-cyclohexyl-6-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.84-7.67 (m, 1H), 7.54-7.00 (m, 6H), 6.99-6.78 (m, 1H), 4.30 (q, J=7.1, 1H), 2.89-2.44 (m, 2H), 2.30 (s, 3H), 1.74 (d, J=3.7, 3H), 1.72-1.48 (m, 6H), 1.44-0.83 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 159.24, 145.78, 141.86, 140.19, 128.31, 127.41, 125.93, 125.85, 120.57, 120.08, 116.43, 57.10, 37.98, 34.09, 25.76, 24.91, 21.72, 18.32.

HRMS (ESI): m/z 334.2257 (M+H)⁺; calc. for C₂₂H₂₈N₃: 334.2283.

139 SM56 N-cyclohexyl-5-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.59-7.02 (m, 8H), 6.92 (dd, J=6.8, 8.9, 1H), 6.42-6.29 (m, 1H), 4.30 (q, J=7.1, 1H), 3.68 (s, 1H), 2.84 (s, 3H), 1.76 (d, J=7.2, 3H), 1.72-1.46 (m, 4H), 1.46-0.83 (m, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 145.91, 143.89, 142.83, 136.00, 128.24, 127.41, 125.83, 123.11, 115.40, 112.92, 59.27, 37.67, 33.57, 33.44, 25.88, 25.18, 24.95, 21.97, 19.81.

HRMS (ESI): m/z 334.2255 (M+H)⁺; calc. for C₂₂H₂₈N₃: 334.2283.

140 SM51 N-cyclopentyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.08-7.90 (m, 1H), 7.60-7.43 (m, 1H), 7.43-7.11 (m, 5H), 7.06 (ddd, J=1.4, 6.7, 9.0, 1H), 6.71 (td, J=1.2, 6.8, 1H), 4.35 (q, J=7.1, 1H), 3.61-3.22 (m, 1H), 2.65-1.98 (m, 2H), 1.86-1.75 (m, 3H), 1.75-1.05 (m, 9H).

¹³C NMR (50 MHz, CDCl₃) δ 145.64, 142.08, 141.11, 128.74, 128.34, 127.42, 122.79, 122.28, 117.18, 111.11, 59.75, 37.93, 33.57, 33.41, 23.55, 21.77.

HRMS (ESI): m/z 306.1950 (M+H)⁺; calc. for C₂₀H₂₄N₃: 306.1970.

141 SM72 N-cyclopentyl-8-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.91 (d, J=7.3, 1H), 7.51-7.10 (m, 5H), 6.89 (d, J=6.8, 1H), 6.65 (t, J=6.7, 1H), 4.43 (q, J=7.2, 1H), 3.44 (dt, J=5.1, 10.2, 1H), 2.65 (s, 3H), 1.83 (d, J=7.2, 3H), 1.79-1.11 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 145.54, 141.38, 128.27, 127.54, 126.79, 125.94, 125.54, 121.71, 120.22, 111.01, 59.93, 38.19, 33.46, 33.36, 23.57, 21.75, 16.74.

HRMS (ESI): m/z 320.2105 (M+H)⁺; calc. for C₂₁H₂₆N₃: 320.2127.

142 SM73 N-cyclopentyl-7-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.89 (d, J=6.9, 1H), 7.52-7.01 (m, 5H), 6.54 (dd, J=1.6, 6.9, 1H), 4.32 (q, J=7.2, 1H), 3.45 (dt, J=5.6, 11.0, 1H), 2.35 (s, 3H), 1.77 (d, J=7.2, 3H), 1.73-1.44 (m, 5H), 1.44-1.04 (m, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 145.76, 141.63, 141.59, 133.64, 128.30, 127.43, 125.92, 124.63, 121.61, 115.65, 113.71, 59.86, 37.88, 33.51, 33.38, 23.57, 21.75, 21.19.

HRMS (ESI): m/z 320.2121 (M+H)⁺; calc. for C₂₁H₂₆N₃: 320.2127.

143 SM74 N-cyclopentyl-6-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.81-7.73 (m, 1H), 7.55-7.06 (m, 5H), 6.91 (dd, J=1.7, 9.1, 1H), 4.32 (q, J=7.2, 1H), 3.58-3.31 (m, 1H), 2.30 (s, 3H), 1.77 (d, J=7.2, 3H), 1.72-1.09 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 145.81, 141.83, 140.20, 138.23, 128.37, 127.46, 127.31, 126.00, 120.72, 120.02, 116.59, 59.67, 37.97, 33.60, 23.62, 21.83, 18.40.

HRMS (ESI): m/z 320.2095 (M+H)⁺; calc. for C₂₁H₂₆N₃: 320.2127.

144 SM75 N-cyclopentyl-5-methyl-2-(1-phenylethyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.46-7.03 (m, 6H), 6.93 (dd, J=6.9, 8.9, 1H), 6.36 (d, J=6.7, 1H), 4.34 (q, J=7.1, 1H), 3.49 (dt, J=5.7, 11.2, 1H), 2.85 (s, 3H), 1.77 (d, J=7.2, 3H), 1.73-1.07 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 145.96, 143.65, 142.86, 136.02, 128.27, 127.42, 127.01, 125.86, 123.16, 115.49, 112.93, 62.31, 37.53, 33.15, 32.74, 23.74, 23.61, 22.04, 19.68.

HRMS (ESI): m/z 320.2106 (M+H)⁺; calc. for C₂₁H₂₆N₃: 320.2127.

145 SM3 N-cyclohexyl-2-(2,3,6-trichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.23-8.07 (m, 1H), 7.62-7.50 (m, 1H), 7.47 (d, J=8.7, 1H), 7.36 (d, J=8.7, 1H), 7.18 (dd, J=1.3, 6.7, 1H), 6.82 (td, J=0.9, 6.7, 1H), 2.77 (m, 2H), 1.85-1.35 (m, 3H), 1.35-0.71 (m, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 141.56, 134.79, 134.48, 133.04, 131.85, 130.54, 128.27, 126.61, 123.79, 122.90, 117.81, 111.69, 56.63, 33.84, 25.63, 24.58.

HRMS (ESI): m/z 394.0645 (M+H)⁺; calc. for C₁₉H₁₉N₃Cl₃: 394.0645.

146 SM4 N-cyclohexyl-2-(2-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.29-8.03 (m, 1H), 7.60-7.39 (m, 2H), 7.33-7.05 (m, 2H), 6.97 (td, J=1.6, 8.2, 1H), 6.77 (td, J=1.1, 6.8, 1H), 3.93 (s, 3H), 3.72-3.26 (m, 1H), 2.91-2.54 (m, 1H), 1.94-1.36 (m, 5H), 1.33-0.81 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 152.17, 148.23, 147.99, 147.32, 142.22, 127.26, 124.54, 123.96, 123.56, 117.67, 112.66, 111.74, 56.95, 56.67, 34.31, 25.93, 25.14.

HRMS (ESI): m/z 340.1824 (M+H)⁺; calc. for C₂₀H₂₃N₃OF: 340.1825.

147 SM6 2-(3-chloro-2-fluorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.27-8.03 (m, 1H), 7.81 (ddd, J=1.8, 6.6, 8.4, 1H), 7.64-7.47 (m, 1H), 7.40 (ddd, J=1.8, 7.1, 8.0, 1H), 7.31-7.03 (m, 2H), 6.80 (td, J=1.2, 6.8, 1H), 3.56-3.17 (m, 1H), 2.87-2.50 (m, 1H), 1.89-1.33 (m, 5H), 1.10 (d, J=7.0, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 157.31, 152.40, 142.05, 129.94, 129.87, 129.58, 127.10, 124.93, 124.84, 124.01, 122.99, 117.47, 111.64, 56.74, 34.04, 25.62, 24.79.

HRMS (ESI): m/z 344.1329 (M+H)⁺; calc. for C₁₉H₂₀N₃FCl: 344.1330.

148 SM7 2-(4-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.13-7.98 (m, 3H), 7.53 (d, J=9.0, 1H), 7.46-7.37 (m, 2H), 7.14 (dd, J=7.8, 9.1, 1H), 6.79 (t, J=6.8, 1H), 3.13-2.84 (m, 2H), 1.95-1.46 (m, 6H), 1.22 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 141.65, 133.09, 132.93, 128.58, 128.26, 123.99, 122.60, 117.45, 111.62, 56.87, 34.23, 25.72, 24.82.

HRMS (ESI): m/z 326.1422 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

149 SM8 N-cyclohexyl-2-(2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.28-7.99 (m, 1H), 7.85-7.71 (m, 1H), 7.66-7.40 (m, 4H), 7.13 (ddd, J=1.3, 6.7, 9.0, 1H), 6.80 (td, J=1.1, 6.8, 1H), 3.28-2.83 (m, 1H), 2.66 (m, 1H), 1.90-1.35 (m, 5H), 1.23-0.80 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.06, 138.17, 135.28, 132.83, 131.21, 128.11, 126.85, 126.14 (q, J=5.1, 1H), 123.49, 122.77, 121.40, 117.59, 111.50, 56.25, 33.81, 25.63, 24.51.

HRMS (ESI): m/z 360.1688 (M+H)⁺; calc. for C₂₀H₂₁N₃F₃: 360.1688.

150 SM11 N-cyclopentyl-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.21-7.90 (m, 3H), 7.55 (dt, J=1.0, 9.1, 1H), 7.22-6.97 (m, 3H), 6.78 (td, J=1.0, 6.8, 1H), 3.63 (m, 1H), 1.93-1.27 (m, 9H).

¹³C NMR (50 MHz, CDCl₃) δ 164.68, 159.78, 141.48, 138.21, 129.01, 128.85, 124.17, 122.53, 117.36, 115.57, 115.15, 111.77, 59.20, 33.55, 23.64.

HRMS (ESI): m/z 296.1560 (M+H)⁺; calc. for C₁₈H₁₉N₃F: 296.1563.

151 SM12 N-cyclopentyl-2-octylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.03 (d, J=6.8, 1H), 7.45 (d, J=9.0, 1H), 7.05 (ddd, J=1.2, 6.5, 8.7, 1H), 6.71 (td, J=1.0, 6.8, 1H), 3.71-3.45 (m, 1H), 2.88-2.51 (m, 2H), 1.92-1.67 (m, 7H), 1.67-1.42 (m, 5H), 1.42-1.11 (m, 10H), 0.87 (m, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 141.31, 139.81, 126.46, 122.81, 122.24, 116.83, 110.95, 59.79, 33.55, 31.90, 29.86, 29.67, 29.49, 29.28, 27.51, 23.60, 22.67, 14.08.

HRMS (ESI): m/z 314.2595 (M+H)⁺; calc. for C₂₀H₃₂N₃: 314.2596.

152 SM13 N-cyclopentyl-2-(2,3,6-trichlorophenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.21-8.10 (m, 1H), 7.59-7.50 (m, 1H), 7.50-7.41 (m, 1H), 7.41-7.33 (m, 1H), 7.16 (ddd, J=1.0, 6.5, 8.0, 1H), 6.82 (td, J=0.8, 6.7, 1H), 3.56-3.28 (m, 2H), 2.79 (d, J=5.6, 1H), 1.79-1.40 (m, 7H), 1.40-1.04 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 148.09, 141.46, 137.64, 134.80, 134.78, 134.50, 131.85, 130.56, 130.01, 128.88, 128.25, 127.27, 123.88, 122.73, 117.79, 114.22, 111.76, 107.50, 59.43, 33.38, 23.41.

HRMS (ESI): m/z 380.0490 (M+H)⁺; calc. for C₁₈H₁₇N₃Cl₃: 380.0488.

153 SM14 N-cyclopentyl-2-(2-fluoro-3-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.14 (d, J=6.9, 1H), 7.65-7.35 (m, 2H), 7.26-7.03 (m, 2H), 6.95 (td, J=1.6, 8.2, 1H), 6.75 (t, J=6.8, 1H), 3.91 (s, 3H), 3.53-3.22 (m, 2H), 1.76-1.07 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 151.87, 147.84, 147.60, 147.01, 141.78, 131.51, 127.51, 124.16, 124.07, 123.62, 122.67, 117.29, 112.37, 111.37, 59.40, 56.29, 33.13, 23.24.

HRMS (ESI): m/z 326.1668 (M+H)⁺; calc. for C₁₉H₂₁N₃OF: 326.1669.

154 SM15 N-cyclopentyl-2-isopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.18-7.92 (m, 1H), 7.49 (m, 1H), 7.14-6.94 (m, 1H), 6.82-6.61 (m, 1H), 3.80-3.47 (m, 1H), 3.32-3.02 (m, 1H), 2.90-2.66 (m, 1H), 1.93-1.68 (m, 4H), 1.68-1.43 (m, 4H), 1.38 (d, J=9.0, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 160.21, 155.76, 138.10, 126.18, 116.34, 105.78, 105.24, 58.19, 37.28, 37.04, 34.17, 25.09, 18.18, 17.96.

HRMS (ESI): m/z 244.1812 (M+H)⁺; calc. for C₁₅H₂₂N₃: 244.1814.

155 SM16 2-(3-chloro-2-fluorophenyl)-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.23 (d, 1H), 7.92-7.86 (m, 1H), 7.55 (d, 1H), 7.48-7.30 (d, 1H), 7.28-7.07 (m, 2H), 6.92-6.76 (m, 1H), 6.56-3.22 (m, 2H), 1.80-1.12 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 157.39, 152.48, 142.01, 138.19, 129.87, 129.62, 127.73, 124.93, 124.50, 124.08, 122.87, 117.52, 111.50, 59.58, 33.30, 23.31.

HRMS (ESI): m/z 330.1173 (M+H)⁺; calc. for C₁₈H₁₈N₃FCl: 330.1173.

156 SM17 N-cyclopentyl-2-(pentan-3-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.06 (dt, J=1.0, 6.8, 1H), 7.49 (d, J=9.1, 1H), 7.04 (ddd, J=1.2, 6.6, 8.9, 1H), 6.71 (td, J=0.9, 6.8, 1H), 3.64 (dt, J=5.3, 10.8, 1H), 3.02-2.73 (m, 1H), 2.62 (ddd, J=6.4, 8.2, 14.6, 1H), 1.96-1.68 (m, 8H), 1.68-1.41 (m, 4H), 1.37 (d, J=6.8, 1H), 0.82 (t, J=7.4, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 142.09, 141.51, 126.28, 122.65, 122.26, 116.94, 110.72, 60.03, 40.98, 33.58, 28.25, 23.65, 12.60.

HRMS (ESI): m/z 272.2125 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

157 SM18 N-cyclopentyl-2-(2-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.13 (d, J=6.9, 1H), 7.78 (d, J=7.5, 1H), 7.66-7.41 (m, 4H), 7.23-7.03 (m, 1H), 6.81 (td, J=0.9, 6.7, 1H), 3.52-3.21 (m, 1H), 3.06-2.78 (m, 1H), 1.40 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 141.03, 135.34, 132.87, 131.23, 129.95, 128.14, 126.72, 126.17 (q, J=5.1), 123.60, 122.64, 121.42, 117.65, 111.59, 59.16, 33.33, 23.35.

HRMS (ESI): m/z 346.1531 (M+H)⁺; calc. for C₁₉H₁₉N₃F₃: 346.1531.

158 SM19 N-cyclopentyl-2-(3-methylthiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.15-8.06 (m, 1H), 7.52 (dt, J=1.0, 9.0, 1H), 7.26 (d, J=5.1, 1H), 7.11 (ddd, J=1.3, 6.7, 9.0, 1H), 6.94 (d, J=5.1, 1H), 6.77 (td, J=1.1, 6.8, 1H), 3.82-3.25 (m, 1H), 3.22-2.92 (m, 1H), 2.43 (s, 4H), 1.88-1.56 (m, 5H), 1.55-1.31 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 141.36, 135.77, 130.47, 129.73, 126.57, 124.33, 124.21, 123.50, 122.49, 117.47, 111.46, 59.35, 33.32, 23.50.

HRMS (ESI): m/z 298.1383 (M+H)⁺; calc. for C₁₇H₂₀N₃S: 298.1378.

159 SM20 N-cyclopentyl-2-cyclopropylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.01 (d, J=6.7, 1H), 7.40 (d, J=8.9, 1H), 7.21-6.91 (m, 1H), 6.91-6.47 (m, 1H), 3.85-3.53 (m, 1H), 3.14-2.48 (m, 1H), 2.21-1.69 (m, 4H), 1.69-1.40 (m, 4H), 1.23-0.79 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 141.47, 140.87, 138.47, 123.06, 122.12, 116.94, 111.17, 60.15, 33.82, 23.86, 8.45, 8.00.

HRMS (ESI): m/z 242.1659 (M+H)⁺; calc. for C₁₅H₂₀N₃: 242.1657.

160 SM21 2-sec-butyl-N-cyclopentylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.13-7.98 (m, 1H), 7.57-7.42 (m, 1H), 7.14-6.98 (m, 1H), 6.85-6.59 (m, 1H), 4.55-3.84 (m, 1H), 3.61 (m, 1H), 2.86 (m, 1H), 2.11-1.40 (m, 11H), 1.34 (d, J=6.9, 3H), 0.85 (t, J=7.4, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 143.56, 141.42, 124.80, 122.89, 122.29, 116.86, 110.94, 59.92, 33.54, 33.51, 29.84, 23.58, 20.73, 12.61.

HRMS (ESI): m/z 258.1970 (M+H)⁺; calc. for C₁₆H₂₄N₃: 258.1970.

161 SM24 2-sec-butyl-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.14-7.93 (m, 1H), 7.48 (m, 1H), 7.04 (ddd, J=1.2, 6.7, 8.8, 1H), 6.71 (td, J=1.1, 6.9, 1H), 3.10-2.63 (m, 2H), 2.12-1.48 (m, 8H), 1.48-1.06 (m, 8H), 0.85 (t, J=7.3, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 143.77, 141.75, 124.39, 123.01, 122.71, 117.13, 111.12, 57.58, 34.55, 33.63, 30.16, 26.09, 25.23, 21.07, 12.87.

HRMS (ESI): m/z 272.2127 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

162 SM26 6-bromo-2-(2-chlorophenyl)-N-cyclohexyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.30 (s, 1H), 7.71-7.54 (m, 1H), 7.52-7.12 (m, 4H), 3.22 (d, J=5.6, 1H), 2.78-2.51 (m, 1H), 2.45 (s, 3H), 1.87-1.33 (m, 5H), 1.23-0.78 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 140.87, 135.76, 134.14, 133.78, 132.60, 132.42, 129.45, 129.16, 126.86, 125.74, 122.98, 116.60, 110.69, 56.52, 33.79, 25.64, 24.56, 22.53.

HRMS (ESI): m/z 418.0686 (M+H)⁺; calc. for C₂₀H₂₂N₃ClBr: 418.0686.

163 SM27 2-(2-chlorophenyl)-N-cyclohexyl-6-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.91 (s, 1H), 7.74-7.54 (m, 1H), 7.52-7.40 (m, 2H), 7.40-7.18 (m, 2H), 6.98 (dd, J=1.7, 9.2, 1H), 3.40-3.07 (m, 1H), 2.82-2.51 (m, 1H), 2.35 (s, 3H), 1.91-1.31 (m, 5H), 1.23-0.80 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 140.71, 135.00, 134.20, 132.48, 129.31, 128.86, 126.74, 125.92, 121.02, 120.30, 116.84, 56.26, 33.80, 25.64, 24.55, 18.37.

HRMS (ESI): m/z 340.1582 (M+H)⁺; calc. for C₂₀H₂₃N₃Cl: 340.1581.

164 SM28 2-(2-chlorophenyl)-N-cyclohexyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.11 (d, 1H), 7.72-7.68 (m, 1H), 7.53-7.26 (m, 4H), 6.72 (dd, 1H), 3.24 (s, 1H), 2.78 (s, 1H), 2.45 (s, 3H), 1.80-1.42 (m, 5H), 1.23-0.97 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 142.4, 135.2, 134.4, 134.7, 133.9, 130.2, 129.3, 127.7, 126.2 123.3, 116.6, 115.3, 57.4, 34.7, 26.4, 25.2, 21.8.

HRMS (ESI): m/z 340.1581 (M+H)⁺; calc. for C₂₀H₂₃N₃Cl: 340.1581.

165 SM29 2-(2-chlorophenyl)-N-cyclohexyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.92 (s, 1H), 7.73-7.67 (m, 1H), 7.58-7.22 (m, 4H), 7.03-6.92 (dd, 1H), 3.37 (s, 1H), 2.72 (s, 1H), 2.38 (s, 3H), 1.85-1.42 (m, 5H), 1.22-1.08 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 146.1, 142.8, 141.3, 139.5, 135.9, 133.3, 130.2, 129.6, 127.2, 122.7, 121.3, 118.6, 57.0, 34.2, 26.5, 25.9, 19.5.

HRMS (ESI): m/z 340.1581 (M+H)⁺; calc. for C₂₀H₂₃N₃Cl: 340.1581.

166 SM30 2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.71-7.68 (m, 1H), 7.52-7.26 (m, 4H), 7.12-7.08 (m, 1H), 6.53-6.46 (d, 1H), 3.25-3.18 (m, 1H), 3.03 (s, 3H), 2.65 (s, 1H), 1.80-1.45 (m, 5H), 1.26-0.81 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 143.15, 137.29, 136.64, 134.56, 132.65, 132.48, 129.22, 128.87, 128.05, 126.71, 123.78, 115.74, 113.16, 58.72, 33.39, 25.67, 24.95, 19.84.

HRMS (ESI): m/z 340.1581 (M+H)⁺; calc. for C₂₀H₂₃N₃Cl: 340.1581.

167 SM32 6-bromo-2-(2-chlorophenyl)-N-cyclopentyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.31 (s, 1H), 7.65 (dd, J=2.5, 6.9, 1H), 7.53-7.11 (m, 4H), 3.50-3.25 (m, 1H), 3.24-3.07 (m, 1H), 2.44 (s, 3H), 1.77-1.04 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 140.72, 135.51, 134.08, 133.66, 132.60, 132.36, 129.39, 129.15, 126.81, 126.38, 122.80, 116.51, 110.69, 59.33, 33.13, 23.20, 22.47.

HRMS (ESI): m/z 404.0528 (M+H)⁺; calc. for C₁₉H₂₀N₃ClBr: 404.0529.

168 SM33 2-(2-chlorophenyl)-N-cyclopentyl-6-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.98-7.90 (m, 1H), 7.67 (dd, J=2.2, 7.2, 1H), 7.52-7.38 (m, 2H), 7.38-7.28 (m, 2H), 7.00 (dd, J=1.8, 9.2, 1H), 3.49-2.94 (m, 2H), 2.36 (s, 3H), 1.73-0.94 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 142.02, 135.00, 134.23, 132.63, 132.55, 129.39, 128.97, 126.87, 126.82, 121.16, 120.27, 116.94, 108.37, 59.32, 33.22, 23.28, 18.24

HRMS (ESI): m/z 326.1422 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

169 SM34 2-(2-chlorophenyl)-N-cyclopentyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.05 (d, J=6.9, 1H), 7.75-7.60 (m, 1H), 7.46 (dd, J=2.1, 7.2, 1H), 7.41-7.16 (m, 3H), 6.64 (dd, J=1.5, 7.0, 1H), 3.49-3.01 (m, 2H), 2.40 (s, 3H), 1.72-1.10 (m, 8H).

¹³C NMR (50 MHz, CDCl₃) δ 142.19, 138.27, 134.80, 134.49, 132.88, 132.79, 129.65, 129.28, 129.20, 127.06, 122.22, 116.13, 114.50, 59.76, 33.45, 23.54, 21.56.

HRMS (ESI): m/z 326.1422 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

170 SM35 2-(2-chlorophenyl)-N-cyclopentyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.03 (ddd, J=0.5, 1.0, 2.4, 1H), 7.74-7.64 (m, 1H), 7.50-7.42 (m, 1H), 7.41-7.26 (m, 2H), 6.94 (d, J=6.7, 1H), 6.72 (t, J=6.7, 1H), 3.47-3.25 (m, 1H), 3.26-3.00 (m, 1H), 2.62 (s, 3H), 1.71-1.41 (m, 6H), 1.41-1.01 (m, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 141.93, 138.20, 134.64, 134.32, 132.84, 132.75, 129.35, 129.00, 127.31, 126.90, 122.49, 120.58, 111.62, 59.43, 33.26, 23.29, 16.71.

HRMS (ESI): m/z 326.1424 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

171 SM36 2-(2-chlorophenyl)-N-cyclopentyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.76-7.61 (m, 1H), 7.56-7.21 (m, 4H), 7.01 (dd, J=6.9, 8.9, 1H), 6.49 (d, J=8.6, 1H), 3.37-3.00 (m, 2H), 2.97 (s, 3H), 1.71-1.28 (m, 6H), 1.28-0.93 (m, 2H).

¹³C NMR (50 MHz, CDCl₃) δ 143.47, 138.45, 137.04, 134.89, 133.05, 132.97, 132.86, 129.60, 129.29, 127.11, 124.22, 116.12, 113.55, 62.36, 32.95, 23.56, 20.16.

HRMS (ESI): m/z 326.1426 (M+H)⁺; calc. for C₁₉H₂₁N₃Cl: 326.1424.

172 SM38 6-bromo-N-cyclopentyl-2-isopropyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.18 (s, 1H), 7.33 (s, 1H), 3.69-3.44 (m, 1H), 3.27-2.96 (m, 1H), 2.88-2.53 (m, 1H), 2.41 (s, 3H), 1.97-1.38 (m, 8H), 1.34 (d, J=6.8, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 145.57, 133.02, 123.33, 122.61, 116.30, 109.91, 109.74, 59.91, 33.56, 26.32, 23.61, 22.73, 22.44.

HRMS (ESI): m/z 336.1077 (M+H)⁺; calc. for C₁₆H₂₃N₃Br: 336.1075.

173 SM39 N-cyclopentyl-2-isopropyl-6-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.86-7.74 (m, 1H), 7.39 (d, J=9.1, 1H), 6.90 (dd, J=1.8, 9.1, 1H), 3.71-3.41 (m, 1H), 3.29-3.00 (m, 1H), 2.31 (s, 3H), 1.91-1.41 (m, 8H), 1.36 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 144.70, 140.54, 125.88, 123.17, 120.44, 120.04, 116.42, 59.75, 33.55, 26.23, 23.64, 22.85, 18.37.

HRMS (ESI): m/z 258.1972 (M+H)⁺; calc. for C₁₆H₂₄N₃: 258.1970.

174 SM40 N-cyclopentyl-2-isopropyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.91 (d, J=7.1, 1H), 7.24 (s, 1H), 6.54 (dd, J=1.4, 7.1, 1H), 3.68-3.46 (m, 1H), 3.24-2.99 (m, 1H), 2.35 (s, 3H), 1.90-1.40 (m, 8H), 1.36 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 144.35, 141.78, 133.46, 121.96, 121.53, 115.42, 113.42, 59.85, 33.41, 26.15, 23.52, 22.71, 21.09.

HRMS (ESI): m/z 258.1969 (M+H)⁺; calc. for C₁₆H₂₄N₃: 258.1970.

175 SM41 N-cyclopentyl-2-isopropyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.00-7.82 (m, 1H), 6.97-6.75 (m, 1H), 6.62 (t, J=6.8, 1H), 3.72-3.43 (m, 1H), 3.33-2.99 (m, 1H), 2.58 (s, 3H), 1.93-1.67 (m, 4H), 1.67-1.43 (m, 4H), 1.39 (d, J=6.9, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 144.27, 141.65, 126.67, 124.17, 121.68, 120.23, 110.86, 59.99, 33.59, 26.71, 23.65, 22.82, 16.87.

HRMS (ESI): m/z 258.1969 (M+H)⁺; calc. for C₁₆H₂₄N₃: 258.1970.

176 SM42 N-cyclopentyl-2-isopropyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.35 (d, J=8.9, 1H), 6.91 (dd, J=6.8, 9.0, 1H), 6.39-6.30 (m, 1H), 3.63-3.38 (m, 1H), 3.15 (q, J=6.8, 1H), 2.96-2.76 (m, 3H), 1.93-1.67 (m, 4H), 1.67-1.41 (m, 4H), 1.41-1.26 (m, 6H).

¹³C NMR (50 MHz, CDCl₃) δ 146.39, 143.09, 135.91, 123.02, 115.29, 115.29, 112.63, 62.55, 32.91, 25.88, 23.65, 22.75, 19.68.

HRMS (ESI): m/z 258.1971 (M+H)⁺; calc. for C₁₆H₂₄N₃: 258.1970.

177 SM44 6-bromo-N-cyclohexyl-2-isopropyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.17 (s, 1H), 7.33 (s, 1H), 3.08 (q, J=6.7, 1H), 2.96-2.59 (m, 2H), 2.41 (s, 3H), 2.02-1.46 (m, 6H), 1.34 (d, J=6.9, 6H), 1.29-1.07 (m, 4H).

¹³C NMR (50 MHz, CDCl₃) δ 145.76, 138.45, 133.21, 122.96, 116.48, 110.14, 100.21, 57.62, 34.47, 26.54, 26.07, 25.16, 22.97, 22.68.

HRMS (ESI): m/z 350.1236 (M+H)⁺; calc. for C₁₇H₂₅N₃Br: 350.1232.

178 SM45 N-cyclohexyl-2-isopropyl-6-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.78 (s, 1H), 7.38 (d, J=9.2, 1H), 6.89 (dd, J=1.7, 9.1, 1H), 3.23-3.00 (m, 1H), 2.97-2.74 (m, 1H), 2.31 (s, 3H), 1.98-1.47 (m, 5H), 1.35 (d, J=6.9, 6H), 1.22-1.09 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 144.63, 140.56, 138.22, 125.82, 120.41, 120.14, 116.41, 57.17, 34.30, 26.22, 25.89, 24.98, 22.86, 18.39.

HRMS (ESI): m/z 272.2126 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

179 SM46 N-cyclohexyl-2-isopropyl-7-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 8.00-7.79 (m, 1H), 7.26 (s, 1H), 6.55 (dd, J=1.5, 7.0, 1H), 3.23-2.93 (m, 2H), 2.93-2.73 (m, 1H), 2.35 (s, 3H), 1.99-1.44 (m, 5H), 1.35 (d, J=6.9, 6H), 1.30-0.99 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 144.44, 142.08, 139.90, 133.86, 122.00, 115.73, 113.81, 57.62, 34.51, 26.47, 26.14, 25.20, 23.03, 21.47.

HRMS (ESI): m/z 272.2126 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

180 SM47 N-cyclohexyl-2-isopropyl-8-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.89 (d, J=6.8, 1H), 7.02-6.73 (m, 1H), 6.61 (t, J=6.7, 1H), 3.28-3.04 (m, 1H), 2.98-2.66 (m, 2H), 2.57 (s, 3H), 1.97-1.50 (m, 5H), 1.38 (d, J=6.9, 6H), 1.31-1.04 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 153.93, 144.41, 141.95, 126.89, 121.84, 120.62, 111.05, 57.61, 34.57, 26.94, 26.14, 25.24, 23.08, 17.13.

HRMS (ESI): m/z 272.2123 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

181 SM48 N-cyclohexyl-2-isopropyl-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.36 (d, J=8.8, 1H), 6.92 (dd, J=6.7, 8.9, 1H), 6.42-6.29 (m, 1H), 3.24-3.00 (m, 1H), 2.89 (s, 3H), 1.97-1.51 (m, 5H), 1.35 (d, J=6.9, 6H), 1.31-0.97 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 144.26, 141.87; 139.92, 138.47, 123.30, 115.64, 112.96, 59.90, 33.82, 26.27, 26.23, 25.46, 23.01, 20.09.

HRMS (ESI): m/z 272.2128 (M+H)⁺; calc. for C₁₇H₂₆N₃: 272.2127.

182 SM81 N,2-bis(2-chlorophenyl)-5-methylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.68-7.49 (m, 2H), 7.49-7.34 (m, 1H), 7.34-7.20 (m, 2H), 7.14 (dd, J=6.8, 9.1, 1H), 7.03-6.84 (m, 1H), 6.65 (td, J=1.2, 7.6, 1H), 6.52 (d, J=6.7, 1H), 6.19 (s, 1H), 6.09 (dd, J=1.1, 8.3, 1H), 2.67 (s, 3H).

¹³C NMR (50 MHz, CDCl₃) δ 144.65, 143.60, 140.64, 138.21, 136.14, 133.24, 132.70, 131.97, 129.61, 129.48, 129.38, 127.82, 126.70, 125.31, 119.47, 118.64, 116.22, 113.90, 113.60, 18.59.

HRMS (ESI): m/z 368.0733 (M+H)⁺; calc. for C₂₀H₁₆N₃Cl₂: 368.0721.

183 SM83 2-(2-chlorophenyl)-N-cyclohexyl-5,7-dimethylimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.71-7.53 (m, 1H), 7.52-7.39 (m, 1H), 7.39-7.20 (m, 2H), 7.14 (s, 1H), 6.29 (s, 1H), 2.91 (s, 3H), 2.54 (m, 1H), 2.31 (s, 3H), 1.58 (m, 5H), 1.11-0.68 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 143.77, 138.20, 135.88, 134.77, 134.58, 132.74, 132.57, 129.31, 128.86, 127.69, 126.79, 116.02, 114.18, 58.77, 33.16, 25.80, 24.76, 20.87, 19.72.

HRMS (ESI): m/z 354.1715 (M+H)⁺; calc. for C₂₁H₂₅N₃Cl: 354.1737.

184 SM92 2-(2-chlorophenyl)-N-cyclohexyl-5-phenoxyimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.68-7.61 (m, 1H), 7.56-7.41 (m, 3H), 7.39-7.28 (m, 3H), 7.28-7.19 (m, 3H), 7.08-6.89 (m, 1H), 5.91 (d, J=7.2, 1H), 2.89-2.80 (m, 1H), 1.78-1.41 (m, 6H), 1.11-0.81 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 156.34, 149.94, 143.46, 138.28, 134.05, 133.85, 131.01, 129.96, 129.24, 128.01, 127.34, 124.91, 120.04, 113.84, 97.02, 57.96, 33.95, 25.74, 25.07.

HRMS (ESI): m/z 418.1635 (M+H)⁺; calc. for C₂₅H₂₅N₃OCl: 418.1686.

185 SM93 2-(2-chlorophenyl)-N-cyclohexyl-5-ethoxyimidazo[1,2-a]pyridin-3-amine

¹H NMR (200 MHz, CDCl₃) δ 7.57 (dd, J=3.3, 6.0, 1H), 7.51-7.39 (m, 1H), 7.38-7.19 (m, 2H), 7.13 (d, J=8.9, 1H), 7.04-6.88 (m, 1H), 5.89 (d, J=7.3, 1H), 4.26 (q, J=7.0, 2H), 4.11 (s, 1H), 2.74 (s, 1H), 1.83-1.63 (m, 2H), 1.63-1.31 (m, 6H), 1.21-0.75 (m, 5H).

¹³C NMR (50 MHz, CDCl₃) δ 150.94, 142.66, 134.48, 134.05, 132.58, 129.41, 128.73, 128.48, 126.29, 123.89, 110.70, 88.54, 65.45, 57.15, 33.42, 25.88, 24.57, 14.46.

HRMS (ESI): m/z 370.1658 (M+H)⁺; calc. for C₂₁H₂₅N₃OCl: 370.1686.

186 DG402-49720 4-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)benzonitrile

¹H NMR (400 MHz, CDCl₃) δ 8.24 (dd, J=1.7, 8.5, 2H), 8.05 (dt, J=1.0, 6.9, 1H), 7.69 (dd, J=1.7, 8.5, 2H), 7.53 (dt, J=1.0, 9.1, 1H), 7.17 (ddd, J=1.2, 6.7, 9.1, 1H), 6.81 (td, J=1.0, 6.8, 1H), 3.06 (d, J=4.9, 1H), 2.95 (ddd, J=4.6, 10.0, 14.4, 1H), 1.87-1.76 (m, 2H), 1.76-1.64 (m, 2H), 1.64-1.51 (m, 1H), 1.33-1.03 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 141.94, 139.17, 134.70, 132.16, 127.17, 126.06, 124.61, 122.63, 119.18, 117.75, 112.04, 110.20, 56.96, 34.22, 25.59, 24.77.

HRMS (ESI): m/z 317.1765 (M+H)⁺; calc. for C₂₀H₂₁N₄: 317.1766.

187 DG402-49722 3-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)benzonitrile

¹H NMR (400 MHz, CDCl₃) δ 8.48 (t, J=1.6, 1H), 8.37 (dt, J=1.5, 7.6, 1H), 8.14-7.94 (m, 1H), 7.62-7.45 (m, 3H), 7.16 (ddd, J=1.1, 6.7, 9.0, 1H), 6.81 (td, J=1.0, 6.8, 1H), 3.04 (d, J=4.7, 1H), 2.94 (ddd, J=4.4, 10.0, 14.3, 1H), 1.88-1.75 (m, 2H), 1.75-1.63 (m, 2H), 1.63-1.49 (m, 1H), 1.42-0.92 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 141.85, 135.91, 134.59, 130.95, 130.44, 130.33, 129.11, 125.29, 124.46, 122.58, 118.98, 117.64, 112.48, 111.96, 56.91, 34.21, 25.58, 24.76.

HRMS (ESI): m/z 317.1775 (M+H)⁺; calc. for C₂₀H₂₁N₄: 317.1766.

188 DG402-49744 7-chloro-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.07 (d, J=7.3, 1H), 7.64 (d, J=5.5, 1H), 7.52 (s, 1H), 7.47 (d, J=6.3, 1H), 7.35 (dd, J=7.1, 12.4, 2H), 6.79 (d, J=7.2, 1H), 3.26 (s, 1H), 2.64 (s, 1H), 1.75-1.61 (m, 2H), 1.56 (s, 2H), 1.47 (s, 1H), 1.15-0.91 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 141.08, 135.68, 133.40, 132.41, 132.35, 130.20, 129.44, 129.28, 126.93, 126.56, 123.19, 116.16, 113.23, 56.41, 33.71, 25.49, 24.46.

189 CW23828a 2-(2-chlorophenyl)-N-cyclohexyl-6-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.25 (s, 1H), 7.70 (dd, J=1.9, 7.5, 1H), 7.60 (dd, J=0.7, 9.3, 1H), 7.54 (d, J=8.8, 2H), 7.48 (dd, J=1.5, 7.7, 1H), 7.43-7.29 (m, 3H), 7.03 (d, J=8.8, 2H), 3.86 (s, 3H), 3.31 (d, J=6.8, 1H), 2.80-2.59 (m, 1H), 1.78-1.63 (m, 2H), 1.63-1.51 (m, 2H), 1.51-1.40 (m, 1H), 1.17-0.89 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 159.32, 140.83, 135.58, 133.97, 132.48, 130.28, 129.41, 129.07, 127.99, 126.88, 126.56, 125.70, 124.48, 119.32, 117.26, 114.43, 56.42, 55.32, 33.79, 25.55, 24.53.

190 CW23828b 2-(2-chlorophenyl)-N-cyclohexyl-5-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 7.62 (dd, J=2.1, 7.3, 1H), 7.60-7.53 (m, 1H), 7.46 (d+m, J=8.7, 3H), 7.37-7.26 (m, 2H), 7.14 (dd, J=6.8, 8.9, 1H), 6.98 (d, J=8.6, 2H), 6.61 (dd, J=1.0, 6.8, 1H), 3.88 (s, 3H), 2.64 (s, 1H), 2.00 (m, 1H), 0.82 (m, 8H), 0.37 (m, 2H).

¹³C NMR (101 MHz, CDCl₃) δ 159.88, 142.70, 138.01, 135.45, 134.19, 133.32, 132.69, 130.78, 129.40, 128.92, 127.99, 127.08, 126.62, 122.99, 116.73, 115.26, 112.64, 56.36, 55.50, 32.47, 25.59, 24.34.

191 CW23825 2-(2-chlorophenyl)-N-cyclohexyl-5-o-tolylimidazo[1,2-a]pyridin-3-amine
192 CW23828c 2-(2-chlorophenyl)-N-cyclohexyl-6-o-tolylimidazo[1,2-a]pyridin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 7.65-7.60 (m, 1H), 7.58 (dd, J=1.2, 9.0, 1H), 7.46-7.19 (m, 7H), 7.15 (dd, J=6.8, 9.0, 1H), 6.57 (dd, J=1.2, 6.8, 1H), 2.45 (d, J=7.8, 1H), 2.07 (s, 3H), 2.01 (ddd, J=3.6, 8.5, 10.1, 1H), 1.41-0.98 (m, 5H), 0.89-0.65 (m, 2H), 0.58 (d, J=12.4, 1H), 0.41-0.27 (m, 1H), 0.27-0.11 (m, 1H).

¹³C NMR (101 MHz, CDCl₃) δ 142.26, 138.77, 137.87, 134.92, 134.19, 133.22, 132.68, 129.34, 129.24, 129.00, 128.97, 128.94, 128.53, 127.75, 127.34, 126.66, 125.06, 122.97, 116.94, 114.82, 56.76, 32.63, 32.50, 25.55, 19.77.

193 DG402-49750 2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyrimidin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.53 (dd, J=2.1, 4.1, 1H), 8.46 (dd, J=2.1, 6.8, 1H), 7.81-7.70 (m, 1H), 7.55-7.43 (m, 1H), 7.38 (dqd, J=1.8, 7.4, 14.8, 2H), 6.90 (dd, J=4.1, 6.8, 1H) 3.34 (d, J=6.9, 1H), 2.64 (dd, J=3.4, 6.7, 1H), 1.73-1.61 (m, 2H), 1.61-1.52 (m, 2H), 1.47 (s, 1H), 1.19-0.91 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 149.13, 144.56, 136.60, 133.27, 132.79, 132.24, 130.42, 129.45, 129.42, 127.01, 124.75, 108.09, 56.60, 33.72, 25.47, 24.46.

HRMS (ESI): m/z 327.1380 (M+H)⁺; calc. for C₁₈H₂₀N₄Cl: 327.1376.

194 DG 402-49752 2-(2-chlorophenyl)-N-cyclohexylimidazo[2,1-a]isoquinolin-3-amine

¹H NMR (400 MHz, CDCl₃) δ 8.66 (d, J=8.0, 1H), 8.00 (d, J=7.3, 1H), 7.75 (dd, J=1.6, 7.5, 1H), 7.71 (d, J=7.0, 1H), 7.62-7.57 (m, 1H), 7.57-7.51 (m, 1H), 7.48 (dd, J=1.2, 7.9, 1H), 7.39 (td, J=1.4, 7.5, 1H), 7.36-7.30 (m, 1H), 7.07 (d, J=7.2, 1 H), 3.29 (d, J=7.1, 1H), 2.78-2.62 (m, 1H), 1.77-1.66 (m, 2H), 1.63-1.51 (m, 2H), 1.51-1.44 (m, 1H), 1.16-0.98 (m, 5H).

¹³C NMR (101 MHz, CDCl₃) δ 139.07, 134.03, 132.69, 132.61, 129.61, 129.43, 129.38, 128.97, 128.12, 127.88, 127.78, 127.05, 126.89, 123.95, 122.72, 120.44, 112.30, 56.93, 33.80, 25.62, 24.60.

HRMS (ESI): m/z 376.1587 (M+H)⁺; calc. for C₂₃H₂₃N₃Cl: 376.1581.

Biological Activity

Table 1 gives selected results for the compounds of the invention against HIV-1 reverse transcriptase in an enzymatic assay and/or whole cell anti-HIV assay.

TABLE 1

IC₅₀values obtained for compounds against HIV-1 reverse transcriptase

enzymatic assay and whole cell anti-HIV assay.

% enzyme activity

Enzymatic
at 50 μM inhibitor
Whole cell MAGI

Compound
Assay IC₅₀(μM)
concentration
anti-HIV IC₅₀(μM)

embedded image

96
6.60
11.8
0.63 (MAGI)

embedded image

82
14.47
20
0.84 (MAGI)

embedded image

81
11.28
17
1.88 (MAGI)

embedded image

99
12.20
20
2.19 (MAGI)

embedded image

118

18.1
2.19 (MAGI)

embedded image

43
10
ND
2.21 (MAGI)

embedded image

74
90
ND
2.36 (MAGI)

embedded image

89
21.76
39.9
2.95 (MAGI)

embedded image

42
4.62
6.1
3.15 (MAGI)

embedded image

48
5.14
5.1
ND

embedded image

97
7.52
12.5
ND

embedded image

170
15.89
13.8
ND

embedded image

104
3.74
3.9
ND

embedded image

163
5.39
10.8
ND

embedded image

165
7.18
18.8
ND

embedded image

8
4.39
7.1
0.16 (PBMC)

embedded image

166
1.55
3.4
ND

embedded image

171
1.43
11.3
ND

embedded image

116
3.47
4.7
ND

Nevirapine
0.7
1.0
0.10 (MAGI)

0.033 (PBMC)

ND: not done

Enzymatic Method for Determining Activity Against Reverse Transcriptase

The assay is based on a sandwich-ELISA protocol employing the ROCHE colorimetric reverse transcriptase kit (cat# 11468120910). Biotin and DIG-labelled nucleotides are incorporated into cDNA strands polymerized on an RNA template by the action of HIV-1 reverse transcriptase. The cDNA products are bound to streptavidin-coated wells of 96-well plate inserts, and their associated DIG-moieties detected by incubation with anti-DIG antibodies conjugated to horseradish peroxidase (HRP). The amount of bound antibody is quantitated by incubation with a colorimetric HRP substrate, followed by absorbance reading at 405 nm using a multiwell spectrophotometer.

To assess the inhibitory activity of test compounds, a single concentration screen (usually 50 μM) or IC₅₀determination may be carried out. In the single concentration screen, compounds are incubated with HIV-1 reverse trancriptase and substrate and the residual enzyme activity expressed as a percentage relative to a control without inhibitor. For IC₅₀determinations, 4-fold serial dilutions of the compounds are incubated with HIV-1 reverse trancriptase and substrate and the enzyme activity, expressed as a percentage relative to a control without inhibitor, plotted against inhibitor concentration to derive the concentration at which 50% enzyme inhibition (IC₅₀) is obtained.

Cellular Methods for Determining Anti-HIV Activity
PBMC

Fresh human PBMCs, seronegative for HIV and HBV, were isolated from screened donors (Interstate Blood Bank, Inc. Memphis, Tenn.). Cells were pelleted/washed 2-3 times by low speed centrifugation and re-suspension in PBS to remove contaminating platelets. The Leukophoresed blood was then diluted 1:1 with Dulbecco's Phosphate Buffered Saline (DPBS) and layered over 14 mL of Lymphocyte Separation Medium (LSM; Cellgro® by Mediatech, Inc.; density 1.078+/−0.002 g/ml; Cat.# 85-072-CL) in a 50 mL centrifuge tube and then centrifuged for 30 minutes at 600×g. Banded PBMCs were gently aspirated from the resulting interface and subsequently washed 2× with PBS by low speed centrifugation. After the final wash, cells were enumerated by trypan blue exclusion and re-suspended at 1×10⁷cells/ml in RPMI 1640 supplemented with 15% Fetal Bovine Serum (FBS), and 2 mM L-glutamine, 4 μg/ml Phytohemagglutinin (PHA-P, Sigma). The cells were allowed to incubate for 48-72 hours at 37° C. After incubation, PBMCs were centrifuged and resuspended in RPMI 1640 with 15% FBS, 2 mM L-glutamine, 100 U/ml penicillin, 100 μg/ml streptomycin, 10 μg/ml gentamycin, and 20 U/ml recombinant human IL-2 (R&D Systems, Inc). IL-2 is included in the culture medium to maintain the cell division initiated by the PHA mitogenic stimulation. PBMCs were maintained in this medium at a concentration of 1−2×10⁶cells/mL with biweekly medium changes until used in the assay protocol. Cells were kept in culture for a maximum of two weeks before being deemed too old for use in assays and discarded. Monocytes were depleted from the culture as the result of adherence to the tissue culture flask.

For the standard PBMC assay, PHA-P stimulated cells from at least two normal donors were pooled (mixed together), diluted in fresh medium to a final concentration of 1×10⁶cells/mL, and plated in the interior wells of a 96 well round bottom microplate at 50 μl/well (5×10⁴cells/well) in a standard format developed by the Infectious Disease Research department of Southern Research Institute. Pooling (mixing) of mononuclear cells from more than one donor is used to minimize the variability observed between individual donors, which results from quantitative and qualitative differences in HIV infection and overall response to the PHA and IL-2 of primary lymphocyte populations. Each plate contains virus/cell control wells (cells plus virus), experimental wells (drug plus cells plus virus) and compound control wells (drug plus media without cells, necessary for MTS monitoring of cytotoxicity). Since HIV-1 is not cytopathic to PBMCs, this allows the use of the same assay plate for both antiviral activity and cytotoxicity measurements. Test drug dilutions were prepared at a 2× concentration in microtiter tubes and 100 μl of each concentration was placed in appropriate wells using the standard format. 50 μl of a predetermined dilution of virus stock was placed in each test well (final MOI≈0.1). The PBMC cultures were maintained for seven days following infection at 37° C., 5% CO₂. After this period, cell-free supernatant samples were collected for analysis of reverse transcriptase activity. Following removal of supernatant samples, compound cytotoxicity was measured by addition of MTS to the plates for determination of cell viability. Wells were also examined microscopically and any abnormalities were noted.

MAGI

MAGI-R5 cells naturally express the CXCR4 co-receptor and are engineered to express CD4 (HIV-1 cell surface receptor), the CCR5 co-receptor and also to contain an LTR-β-galactosidase reporter construct. The MAGI Antiviral Assay is designed to identify compounds that block HIV-1 replication via targets in the viral life cycle up to and including Tat transactivation (e.g. virus attachment/fusion/entry, uncoating, reverse transcription, nuclear import, integration, LTR transactivation). MAGI cells are treated with compound for 15 to 30 min prior to addition of virus. HIV-1 is then added to the cells/compounds and the cultures are incubated for 48 hours. If the virus is able to infect the cells it will proceed through reverse transcription and integration and begin transcription from the integrated provirus. One of the first virus proteins produced is HIV 1 Tat, which transactivates the HIV-1 LTR promoter driving expression of β-galactosidase. As a result, infected cells begin to overproduce the β-galactosidase enzyme. Forty-eight hours post infection, the cells are lysed and β-galactosidase enzyme activity is measured using a chemiluminescence detection method (Perkin Elmer Applied Biosystems). Compound toxicity is monitored on replicate plates using MTS dye reduction (CellTiter 96® Reagent, Promega, Madison, Wis.).

The invention accordingly shows that compounds of the general structure A and B inhibit the enzyme HIV-1 reverse transcriptase and thus have application as anti-HIV agents.

PCT/US2008/082531 claims the priority of U.S. Ser. No. 60/986,990. However, at the time of filing this application, the priority document was not available from the US Patent Office. If the priority date of any compounds disclosed in PCT/US2008/082531 is later than the priority date of the compounds disclosed in this specification it will be necessary to amend the provisos. The following has therefore been included in this specification to provide for this eventuality.

The invention also provides the use of a compound selected from compounds of the formula A and B in the manufacture of a medicament for the treatment of a subject infected with HIV, a composition for use in treating a subject who has been infected with HIV, the composition including a compound selected from compounds of formula A or B, for use in the treatment of a subject suffering from an HIV infection, a method of treating a subject suffering from an HIV infection by administration of a compound selected from compounds of formula A or B and compounds of formula A or B in which, for formula A

- R is selected from alkyl, branched alkyl, cycloalkyl, aryl, substituted aryl, naphthyl, benzyl and bicycloalkyl,
- R¹is selected from alkyl, cycloalkyl, substituted alkyl, branched alkyl, phenyl, heteroaryl, oxacycloalkyl, bicycloalkyl, furyl, substituted furyl, thienyl and substituted thienyl

R²-R⁵are independently selected from H, halogen, cyano, alkyl and substituted alkyl, or R²and R³together form a carbocyclic ring or, independently, R⁴and R⁵together form a carbocyclic ring,

R⁶is H, alkyl or alkanoyl,

and in which for formula B,

- R is cycloalkyl and R¹is substituted aryl provided that compounds disclosed in U.S. Ser. No. 60/986,990 are excluded.

IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS

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