Synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazine derivatives by palladium-catalyzed cross-coupling reactions

Synthesis

Volumn , Issue 3, 2007, Pages 0367-0374

  Popowycz, Florence ^a   Bernard, Philippe ^b   Raboisson, Pierre ^b   Joseph, Benoît ^a  

^a UNIVERSITÉ LYON 1   (France)

^b Greenpharma SA   (France)

Author keywords

Bioisosteres; Palladium; Purine; Pyrazolo 1,5 a 1,3,5 triazine

Indexed keywords

BIOISOSTERES; CROSS-COUPLING REACTIONS; PURINE; PYRAZOLO[1,5-A]-1,3,5-TRIAZINE;

CATALYSIS; ESTERS; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DERIVATIVES;

4 (N METHYL N PHENYLAMINO) 2 METHYLSULFANYL 8 (PHENTYN 1YL)PYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 4 (N METHYL N PHENYLAMINO) 2 METHYLSULFANYL 8 PHENYL 2 PROPYLPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 4 (N METHYL N PHENYLAMINO) 2 METHYLSULFANYL 8 PHENYLPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 4 (N METHYL N PHENYLAMINO) 8 (PHENTYN 1YL) 2 PROPYLPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 4 (N METHYL N PHENYLAMINO) 8 (PHENTYN 1YL)PYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 4 (N METHYL N PHENYLAMINO) 8 PHENYLPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 8 ACETYL 4 (N METHYL N PHENYLAMINO) 2 METHYLSULFANYLPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 8 ACETYL 4 (N METHYL N PHENYLAMINO) 2 PROPYLPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 8 ACETYL 4 (N METHYL N PHENYLAMINO)PYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; 8 IODOPYRAZOLO[1,5 A] 1,3,5 TRIAZENE DERIVATIVE; HYPOXANTHINE DERIVATIVE; LETEPRINIM; PALLADIUM; TERT BUTYL 3 [4 (N METHYL N PHENYLAMINO) 2 METHYLSULFANYLPYRAZOLO[1,5 A] 1,3,5 TRIAZIN 8 YL]PROP 2 ENOATE; TERT BUTYL 3 [4 (N METHYL N PHENYLAMINO) 2 PROPYLPYRAZOLO[1,5 A] 1,3,5 TRIAZIN 8 YL]PROP 2 ENOATE; TERT BUTYL 3 [4 (N METHYL N PHENYLAMINO)PYRAZOLO[1,5 A] 1,3,5 TRIAZIN 8 YL]PROP 2 ENOATE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; NONHUMAN; SONOGASHIRA REACTION; STILLE REACTION; SUBSTITUTION REACTION; SUZUKI REACTION;

EID: 33947511834     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958963     Document Type: Article

References (24)

1. Senga, K.; O'Brien, D. E.; Scholten, M. B.; Novinson, T.; Miller, J. P.; Robins, R. K. J. Med. Chem. 1982, 25, 243.
2. (a) Gilligan, P. J.; Folmer, B. K.; Hartz, R. A.; Koch, S.; Nanda, K. K.; Andreuski, S.; Fitzgerald, L.; Miller, K.; Marshall, W. J. Bioorg. Med. Chem. 2003, 11, 4093.
3. (b) He, L.; Gilligan, P. J.; Zaczek, R.; Fitzgerald, L. W.; McElroy, J.; Shen, H.-S. L.; Saye, J. A.; Kalin, N. H.; Shelton, S.; Christ, D.; Trainor, G.; Hartig, P.J. Med. Chem. 2000, 43, 449.
4. Almansa, C.; de Arriba, A. F.; Cavalcanti, F. L.; Gómez, L. A.; Miralles, A.; Merlos, M.; García-Rafanell, J.; Forn, J. J. Med. Chem. 2001, 44, 350.
5. (a) Prevost, G.; Lonchampt, M.-O.; Kim, S.; Morgan, B.; Ulibarri, G.; Thurieau, C. PCT Int. Appl. WO 2002050079, Chem. Abstr. 2002, 137, 47234.
6. (b) Guzi, T. J.; Paruch, K. US Patent US 2005187219, Chem. Abstr. 2005, 143, 248417.
7. Lübbers, T.; Angehrn, P.; Gmünder, H.; Herzig, S.; Kulhanek, J. Bioorg. Med. Chem. Lett. 2000, 10, 821.
8. Subramanyam, C.; Ault, B.; Sawutz, D.; Bacon, E. R.; Singh, B.; Pennock, P. O.; Kelly, M. D.; Kraynak, M.; Krafte, D.; Treasurywala, A. J. Med. Chem. 1995, 38, 587.
9. Glasky, A. J.; Glasky, M. S.; Ritzmann, R. F.; Rathbone, M. P. Exp. Opin. Invest. Drugs 1997, 6, 1413.
10. Rathbone, M. P.; Middlemiss, P. J.; Crocker, C. E.; Glasky, M. S.; Juurlink, B. H. J.; Ramirez, J. J.; Cicarelli, R.; Di Ioro, P.; Caciagli, F. Exp. Opin. Invest. Drugs 1999, 8, 1255.
11. Grundman, M.; Caparelli, E.; Kim, H. T.; Morris, J. C.; Farlow, M.; Rubin, E. H.; Heidebrink, J.; Hake, A.; Ho, G.; Schultz, A. N.; Schafer, K.; Houston, W.; Thomas, R.; Thal, L. J. Life Sci. 2003, 73, 539.
12. Holmes, M.; Maysinger, D.; Foerster, D.; Pertens, E.; Barlas, C.; Diamond, J. Mol. Cell. Neurosci. 2003, 24, 568.
13. Glasky, A. J. PCT Int. Appl. WO 9957119, Chem. Abstr. 1999, 131, 322486.
14. (a) Zhang, H.-C.; Brakta, M.; Daves, G. D. Jr. Tetrahedron Lett. 1993, 34, 1571.
15. (b) Zhang, H.-C.; Daves, G. D. Jr. Organometallics 1993, 12, 1499.
16. (c) Zhang, H.-C.; Brakta, M.; Daves, G. D. Jr. Nucleosides Nucleotides 1995, 14, 105.
17. Raboisson, P.; Baurand, A.; Cazenave, J.-P.; Gachet, C.; Schultz, D.; Spiess, B.; Bourguignon, J.-J. J. Org. Chem. 2002, 67, 8063.
18. (a) Kobe, J.; Robins, R. K.; O'Brien, D. E. J. Heterocycl. Chem. 1974, 199.
19. (b) Tam, S. Y.-K.; Klein, R. S.; Wempen, I.; Fox, J. J. J. Org. Chem. 1979, 44, 4547.
20. (c) Vogel, A.; Troxler, F. Helv. Chim. Acta 1975, 58, 761.
21. (a) Raboisson, P.; Schultz, D.; Lugnier, C.; Bourguignon, J.-J. Tetrahedron Lett. 2002, 43, 9501.
22. (b) Raboisson, P.; Schultz, D.; Lugnier, C.; Mathieu, R.; Bourguignon, J.-J. Tetrahedron Lett. 2003, 44, 703.
23. Liu, Y.; Li, K. Macromol. Rapid Commun. 2002, 23, 739.
24. Bernard, P.; Raboisson, P.; Joseph, B. PCT Int. Appl. WO 2004011464, Chem. Abstr. 2004, 140, 146171.