Claims
- 1. A method for the synthesis of a compound or an array of compounds of Formula I:
- 2. The method of claim 1 wherein a compound or an array of compounds of Formula 6 is treated with a compound or an array of compounds of Formula 7 to form a compound or an array of compounds of Formula 8.
- 3. The method of claim 2 wherein the base in step (i) is a tertiary amine.
- 4. The method of claim 3 wherein the tertiary amine is selected from the group consisting of diisopropylethylamine, triethylamine, N-methylmorpholine and lutidine.
- 5. The method of claim 4 wherein the inert solvent in step (ii) is selected from the group consisting of toluene, tetrahydrofuran, hexanes and CH2Cl2.
- 6. The method of claim 5 wherein the compound of Formula 4 in step (ii) is trimethylsilyl diazomethane.
- 7. The method of claim 6 wherein the deprotecting agent in step (iv) is selected from the group consisting of trifluoroacetic acid and silver triflate.
- 8. The method of claim 7 wherein the compound of Formula 7 in step (iv) is an isocyanate represented by R2—N═C═O.
- 9. The method of claim 8 wherein step (iv) utilizes a solution of a compound of Formula 8 in pyridine, tetrahydrofuran, dioxane or mixtures thereof.
- 10. The method of claim 9 wherein step (v) is carried out in the presence of a base selected from the group consisting of triethylamine and diisopropyl ethyl amine.
- 11. The method of claim 10 wherein:
R1 is selected from the group consisting of C1-8alkyl; (CH2)1-2-Ph; 4-methoxybenzyl; 4-methoxyphenylethyl; 3,4-dimethoxybenzyl; 2-benzyloxyethyl; 2-benzyloxypropyl; 3-methoxy-2-benzyloxyethyl; and 3-trifloromethyl-2-benzyloxyethyl; R2 is selected from the group consisting of methyl, ethyl, i-propyl, propyl, t-butyl, cyclohexyl, phenylethyl, benzyl, CH2—CH═CH2, 1-(3-isopropenylphenyl)-1-methylethyl and 1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl; and R3 is selected from the group consisting of 2-hydroxy-1-hydroxymethyl-2-phenylethyl; 2-hydroxy-1-hydroxymethyl-3-methylpentyl; 1-benzyl-2-hydroxyethyl; 1-hydroxymethyl-3-methylbutyl; 4-amino-piperidine-1-carboxylic acid ethyl ester; 2-acetylaminoethyl; 2-diethylaminoethyl; 2-(2-hydroxyethoxy)ethyl; 3-diethylaminopropyl; 3-hydroxypropyl; 6-hydroxyhexyl; 3-imidazol-1-yl-propyl; 2-(4-sulfamoylphenyl)ethyl; 3-(4-methylpiperazin-1-yl)-propyl; 2-dimethylamino-1-methylethyl; 2-[bis-(2-hydroxy-ethyl)amino]ethyl; 1-carbamoyl-2-phenylethyl; 2-dibutylaminoethyl; 5-hydroxy-4,4-dimethylpentyl; 3-dimethylamino-2,2-dimethylpropyl; 2-(butylethylamino)ethyl; 2-diisobutylaminoethyl; 2-hydroxybutylamino; 3-hydroxy-2,2-dimethylpropyl; cyclohexyl; (5-hydroxy-1,3,3-trimethylcyclohexylmethyl); 1,2,3,4-tetrahydronaphthalen-1-yl; cyclooctyl; 3-(2-oxopyrrolidin-1-yl)-propyl; indan-1-yl; (tetrahydrofuran-2-ylmethyl)-; 2-(1 h-indol-3-yl)-ethyl; (benzo[1,3]dioxol-5-ylmethyl); 3-morpholin-4-yl-propyl; 2-pyridin-2-yl-ethyl; 2-hydroxy-1-methyl-2-phenylethyl; 1-methoxyethyl; 1-methyl-3-phenylpropyl; 3-diethyl-1-methylpropyl; benzyl; 2-fluorobenzyl; 2-methoxybenzyl; 3-trifluoromethylbenzyl; 2-phenylaminoethyl; 2-methoxyethyl; phenylethyl; 2-(2-methoxyphenyl)ethyl; 2-(3,4-dimethoxyphenyl)ethyl; 2-(4-chlorophenyl)ethyl; 2-(4-methoxy-phenyl)ethyl; 2-(4-hydroxyphenyl)ethyl; 3,3-diphenylpropyl; 2,5-dimethylbenzyl; 2-trifluoromethylbenzyl; butyl; 1,2-diethyl-pyrazolidin-4-yl; 3-methoxypropyl; 2-diisopropylaminoethyl; 1-isopropyl-2-methylpropyl; 3-m-tolylaminopentyl; 3-butoxypropyl; 1-(4-fluorophenyl)ethyl; 1-methoxymethylpropyl; 2,3-dimethoxybenzyl; 2,4-dimethoxybenzyl; 2-(2-chloro-6-fluorobenzylsulfanyl)ethyl; 2,6-dimethoxybenzyl; 3,5-dimethoxybenzyl; 2-phenoxyethyl; 1-benzylpyrrolidin-3-yl; 2-(2,3-dimethoxyphenyl)ethyl; 2-(2,5-dimethoxyphenyl)ethyl; 2-(2-ethoxyphenyl)ethyl; 2-(3,5-dimethoxyphenyl)ethyl; 2-(4-ethoxyphenyl)ethyl; 2-(4-trifluoromethoxyphenyl)ethyl; 2-hydroxy-1,2-diphenylethyl; 2-hydroxy-1,2-diphenylethyl; 2-(2-hydroxymethylphenylsulfanyl) benzyl, 2-(3-fluorophenyl)ethyl; 2-(2-aminophenyl)benzyl; 2-(2-fluorophenyl)ethyl; 4-aminobenzyl; 2-(3,4-dimethoxyphenyl)ethyl; 1,2-dihydroxy-2-(4-methylsulfanylphenyl)ethyl; 2-hydroxycyclohexyl; 3-(methylphenylamino)propyl; piperonyl; phenyl-N-methylpropyl; hydroxyethyloxyethyl; 2-indolinyl ethyl; and benzyl.
- 12. A method for synthesizing a compound or an array of compounds of Formula 5:
- 13. A method for synthesizing a compound or an array of compounds of Formula 6:
- 14. A method for synthesizing a compound or an array of compounds of Formula 8:
- 15. A compound of Formula 5:
- 16. A compound of Formula 6:
- 17. A compound of Formula 8:
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application claims the benefit of U.S. Provisional Application No. 60/168,836, filed on Dec. 3, 1999.
Provisional Applications (1)
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Number |
Date |
Country |
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60168836 |
Jan 2001 |
US |