Claims
- 1. A method of preparing a compound represented by structural formula IIa:
- 2. The method of claim 1 wherein X is a covalent bond, or a linking group selected from a methanone, a sulfone, or a sulfoxide.
- 3. The method of claim 1 wherein R0 and R3 are independently —H, or a substituted or unsubstituted aliphatic group.
- 4. The method of claim 3 wherein if R3 is —H, at least one of R2 is a secondary or tertiary alkyl group, or a substituted or unsubstituted aryl group.
- 5. The method of claim 1 wherein X is methanone.
- 6. The method of claim 4 wherein:
a. R2 is a substituted or unsubstituted cyclic aliphatic group, or —CH(Rc)2, —C(Rc)3, and each Rc is independently a C1-C4 alkyl group; and b. each R4 is —H, —CH3, —CH2CH3, —CH2CH2CH3, —CH(CH3)2—C(CH3)3, phenyl; or both R4 groups, taken together with the nitrogen atom to which they are bonded, are a cyclic group as shown below: 62wherein n is 0, 1, or 2.
- 7. A method of preparing a compound represented by structural formula IIb:
- 8. The method of claim 7 wherein X is methanone, sulfone, or sulfoxide.
- 9. The method of claim 7 wherein:
a. R2 is a substituted or unsubstituted cyclic aliphatic group, or a substituted or unsubstituted pheyl group, or —CH(Rc)2 or —C(Rc)3, where each Rc is independently a C1-C4 alkyl group; and b. each R4 is —H, —CH3, —CH2CH3, —CH2CH2CH3, —CH(CH3)2—C(CH3)3, phenyl; or both R4 groups, taken together with the nitrogen atom to which they are bonded, are a cyclic group as shown below: 67wherein n is 0, 1, or 2.
- 10. The method of claim 9 wherein each R2 is independently —CH(CH3)2, —C(CH3)3, cyclobutyl, 2,2′,4,4′-tetramethylcyclobutyl, cyclopentyl, 2,2′,5,5′-tetramethlycyclopentyl, cyclohexyl, 2,2′,6,6′-tetramethlycyclohexyl, phenyl, or 2,6-dimethylphenyl.
- 11. The method of claim 7 wherein both R2 groups, taken together, are —(CR52)n— and n is 1, 2, or 3 and each R5 is independently —H or —CH3.
- 12. The method of claim 7 wherein both R2, taken together, are represented by ring C:
- 13. The method of claim 12 wherein ring C is unsubstituted.
- 14. The method of claim 7 wherein R2 is —C(CH3)3.
- 15. The method of claim 7 wherein R4 is —CH3.
- 16. A method of preparing a compound represented by structural formula IIb:
- 17. The method of claim 16 wherein each R2 is —C(CH3)3.
- 18. The method of claim 16 wherein each R4 is —CH3.
- 19. The method of claim 18 wherein R0 and R3 are both —H.
- 20. The method of claim 18 wherein ring B is optionally substituted with one or more groups selected from —F, —Cl, —Br, C1-C4 alkyl, C1-C4 alkoxy, —C1-C4 haloalkyl, C1-C4 haloalkoxy, —NH2, —NO2, or —CN.
- 21. The method of claim 18 wherein ring B is unsubstituted and R1 is a phenyl, pyridyl, furanyl, thienyl, pyrazolyl, or pyrrolyl group substituted with zero, one or more substituents selected from: —Br, —Cl, —F, —Ra, —ORa, —CN, —COORa, —N(Ra)2, —CON(Ra)2, —NRaCORb, —NHCONH2, or —SO2N(Ra)2.
- 22. The method of claim 19 wherein the compound represented by structural formula IIb is further reacted with oxalyl chloride or a synthetic equivalent thereof to form a first intermediate; and reacting the first intermediate with NHR7R8 to form a compound represented by structural formula I;
- 23. The method of claim 22 wherein R7 is H and R8 is represented by a structural formula selected from:
- 24. The method of claim 23 wherein R8 is represented by a structural formula selected from:
- 25. A method of preparing a compound represented by structural formula VII:
- 26. The method of claim 25 wherein the compound represented by structural formula VII is further reacted with oxalyl chloride or a synthetic equivalent thereof to form a first intermediate; and reacting the first intermediate with NHR7R8 to form a compound represented by the following structural formula;
- 27. The method of claim 26 wherein R8 is represented by a structural formula selected from:
- 28. The method of claim 27 wherein R8 is represented by structural formula xxv and R13 is methyl.
- 29. The method of claim 28 wherein R14 is —CN.
- 30. The method of claim 7 wherein R0 and R3 are H, further comprising the steps of reacting the compound represented by structural formula IIb with oxalyl chloride or a synthetic equivalent thereof to form a first intermediate; and reacting the first intermediate with NHR7R8 to form a compound represented by structural formula I;
RELATED APPLICATIONS
[0001] This application claims the benefit of U.S. Provisional Application Serial No. 60/410,679, filed Sep. 13, 2002, the entire teachings of which are incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60410679 |
Sep 2002 |
US |