Claims
- 1. A process for the preparation of a sulfonamide of formula II:
- 2. The process of claim 1, wherein X and Y are each halo.
- 3. The process of claim 1, wherein X is 2-chloro or 2-fluoro and Y is 4-chloro.
- 4. The process of claim 1, wherein R is a substituted or unsubstituted heterocyclyl, the substituents comprising one or more members selected from the group consisting of halo C1-20 alkyl, C1-20 alkoxy, nitro, amino, amido, alkylthio, aryl, arylthio, aryloxy, alkylsulfonyl, and arylsulfonyl.
- 5. The process of claim 4, wherein R is 4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl, 1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedion-3-yl, or 1-amino-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedion-3-yl.
- 6. The process of claim 1, wherein R1 is aryl or alkyl and Z is halo or anhydridyl.
- 7. The process of claim 6, wherein R1 is methyl and Z is chloro.
- 8. The process of claim 1, wherein X is 2-chloro; Y is 4-chloro; R is 4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl; and R1 is methyl.
- 9. The process of claim 1, wherein the amide B-1 and tertiary amine B-2 are independently selected from the group consisting of 1-methyl-2-pyrrolidinone, 1,1,3,3-tetramethylurea, N,N-dimethylacetamide, hexamethylphosphoramide, isoquinoline, and 1-(2,4-dichloro-5-acetamidophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1H-1,2,4-triazol-5-one.
- 10. The process of claim 1, wherein the reaction is carried out in a solvent.
- 11. The process of claim 10, wherein the solvent is an aromatic, alkane, or alkene solvent.
- 12. The process of claim 11, wherein the solvent is selected from the group consisting of toluene, xylene, and diethylbenzene.
- 13. The process of claim 12, wherein the solvent is toluene.
- 14. The process of claim 1, wherein the reaction mixture is heated at about 110° C. to about 160° C. for about three to about 12 hours.
- 15. The process of claim 14, wherein the reaction mixture is heated at about 120° C. to about 150° C. for about three to about seven hours.
- 16. The process of claim 1, wherein about 1 to about 5 molar equivalents of sulfonating agent A are present per one molar equivalent of aniline I.
- 17. The process of claim 16, wherein about 1.3 to about 4 molar equivalents of sulfonating agent A are present per one molar equivalent of aniline I.
- 18. A process for the preparation of a sulfonamide of formula II:
- 19. The process of claim 18, wherein X and Y are each halo.
- 20. The process of claim 19, wherein X is 2-chloro or 2-fluoro and Y is 4-chloro.
- 21. The process of claim 18, wherein R is a substituted or unsubstituted heterocyclyl, the substituents comprising one or more members selected from the group consisting of halo, C1-20 alkyl, C1-20 alkoxy, nitro, amino, amido, alkylthio, aryloxy, aryl, arylthio, alkylsulfonyl, and arylsulfonyl.
- 22. The process of claim 21, wherein R is 4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl, 1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedion-3-yl, or 1-amino-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedion-3-yl.
- 23. The process of claim 18, wherein R1 is alkyl and Z is halo.
- 24. The process of claim 23, wherein R1 is methyl and Z is chloro.
- 25. The process of claim 18, wherein X is 2-chloro; Y is 4-chloro; R is 4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl; and R1 is methyl.
- 26. The process of claim 18, wherein the reaction is carried out in a solvent.
- 27. The process of claim 26, wherein the solvent is an aromatic, alkane, or alkene solvent.
- 28. The process of claim 27, wherein the solvent is selected from the group consisting of toluene, xylene, and diethylbenzene.
- 29. The process of claim 18, wherein the reaction mixture is heated at about 125° C. to about 150° C. for about four to about seven hours.
- 30. The process of claim 18, wherein about 1.5 to about 6 molar equivalents of sulfonating agent A are present per one molar equivalent of aniline I.
- 31. The process of claim 30, wherein about 1.5 to about 4 molar equivalents of sulfonating agent A are present per one molar equivalent of aniline I.
- 32. The process of claim 18, wherein about 0.001 to about 0.09 molar equivalent of N,N-dimethylformamide is present per one molar equivalent of aniline I.
- 33. The process of claim 32, wherein about 0.001 to about 0.05 molar equivalent of N,N-dimethylformamide is present per one molar equivalent of aniline I.
RELATED APPLICATIONS
[0001] This application claims the benefit of U.S. Provisional Application No. 60/209,374, filed on Jun. 5, 2000.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US01/17931 |
6/1/2001 |
WO |
|