Practical synthesis of a potent bradykinin B1 antagonist via enantioselective hydrogenation of a pyridyl N-acyl enamide

Journal of Organic Chemistry

Volumn 74, Issue 12, 2009, Pages 4547-4553

  O'Shea, Paul D ^a   Gauvreau, Danny ^a   Gosselin, Francis ^a   Hughes, Greg ^a   Nadeau, Christian ^a   Roy, Amélie ^a   Shultz, C Scott ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDATION; CHEMICAL EQUATIONS; CROSS-COUPLING; EFFICIENT SYNTHESIS; ENAMIDE; ENANTIOSELECTIVE HYDROGENATION; PYRIDYL;

FLUORINE; PYRIDINE; STEREOCHEMISTRY;

HYDROGENATION;

5 BROMO 3 FLUOROPYRIDINE 2 CARBONITRILE; BRADYKININ B1 RECEPTOR ANTAGONIST; FLUORINE; N [1 (5 BROMO 3 FLUOROPYRIDIN 2 YL)VINYL]ACETAMIDE; N[ 1 (5 BROMO 3 FLUOROPYRIDIN 2 YL)ETHYL]ACETAMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; NITRATION; PRODUCTIVITY; STEREOCHEMISTRY;

AMIDES; AMINES; AZOLES; BORONIC ACIDS; HYDROCARBONS, FLUORINATED; HYDROGENATION; METHYLATION; PYRIDINES; RECEPTOR, BRADYKININ B1; STEREOISOMERISM;

EID: 67249089670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802772d     Document Type: Article

References (45)

1. Bock, M. G.; Longmore, J. Curr. Opin. Chem. Biol. 2000, 4, 401.
2. Regoli, D.; Barabé, J. Pharmacol. Rev. 1980, 32, 1.
3. Bock, M. G.; Hess, J. F.; Pettibone, D. J. In Annual Reports in Medicinal Chemistry; Doherty, A. M., Ed.; Elsevier: New York, 2003; Vol.38, p 111.
4. (a) Calixto, J. B.; Cabrini, D. A.; Ferreira, J.; Campos, M. M. Pain 2000, 87, 1.
5. (b) Calixto, J. B.; Cabrini, D. A.; Ferreira, J.; Campos, M. M. Curr. Opin. Anaesthesiol. 2001, 14, 519.
6. (c) Marceau, F. Immunopharmacology 1995, 30, 1.
7. Feng, D.-M.; DiPardo, R. M.; Wai, J. M.; Chang, R. K.; Di Marco, C. N.; Murphy, K. L.; Ransom, R. W.; Reiss, D. R.; Tang, C.; Prueksaritanont, T.; Pettibone, D. J.; Bock, M. G.; Kuduk, S. D. Bioorg. Med. Chem. Lett. 2008, 18, 682.
8. Pearson, D. E.; Wysong, R. D.; Breder, C. V. J. Org. Chem. 1967, 32, 2358.
9. Knochel, P.; Dohle, W.; Kneisel, F. F.; Kopp, K.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302.
10. (a) Sugimoto, O.; Mori, M.; Tanji, K.-I. Tetrahedron Lett. 1999, 40, 7477.
11. (b) Sugimoto, O.; Mori, M.; Tanji, K.-I. Helv. Chim. Acta 2001, 84, 1112.
12. Kato, Y.; Okada, S.; Tomimoto, K.; Mase, T. Tetrahedron Lett. 2001, 42, 4849.
13. Quallich, G. J.; Fox, D. E.; Friedmann, R. C.; Murtiashaw, C. W. J. Org. Chem. 1992, 57, 761.
14. Ellis, G. T.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779.
15. Fukuhara, T.; Yoneda, N.; Suzuki, A. J. Fluorine Chem. 1987, 38, 435.
16. (a) Roe, A.; Hawkins, G. F. J. Am. Chem. Soc. 1947, 69, 2443.
17. (b) Hawkins, G. F.; Roe, A. J. Org. Chem. 1949, 14, 328.
18. (c) Link, W. J.; Borne, R. F.; Sethiff, F. L. J. Heterocycl. Chem. 1967, 4, 641.
19. (d) Milner, D. J. Synth. Commun. 1992, 22, 73.
20. (a) Finger, G. C.; Kruse, C. W. J. Am. Chem. Soc. 1956, 78, 6034.
21. (b) Adams, D. J.; Clark, J. H.; Nightingale, D. J. Tetrahedron 1999, 55, 7725.
22. Kuduk, S. D.; DiPurdo, R. M.; Bock, M. G. Org. Lett. 2005, 7, 577.
23. Chelucci, G.; Baldino, S.; Chessa, S. Tetrahedron 2006, 62, 619.
24. Skupinska, K. A.; McEachern, E. J.; Baird, I. R.; Skerlj, R. T.; Bridger, G. J. J. Org. Chem. 2003, 68, 3546.
25. Chelucci, G. Tetrahedron: Asymmetry 2005, 16, 2353.
26. (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
27. (b) Zeng, Q. H.; Hu, X. P.; Duan, Z. C.; Liang, X. M.; Zheng, Z. J. Org. Chem. 2006, 71, 393.
28. (c) Enthaler, S.; Hagemann, B.; Junge, K.; Erre, G.; Beller, M. Eur. J. Org. Chem. 2006, 2912.
29. (d) Stemmler, R. T.; Bolm, C. Tetrahedron Lett. 2007, 48, 6189.
30. (a) Cataviela, C.; Mayoral, J. A.; Meléndez, E.; Oro, L. A.; Pinillos, M. T.; Uson, R. J. Org. Chem. 1984, 49, 2503.
31. (b) Bozell, J. J.; Vogt, C. E.; Gozum, J. J. Org. Chem. 1991, 56, 2584.
32. (c) Döbler, C.; Kreuzfeld, H. J.; Michalik, M.; Krause, H. W. Tetrahedron: Asymmetry 1996, 7, 117.
33. (d) Wang, B.; Wang, T. Patent WO2006/123113, 2006.
34. Savarin, C. G.; Boice, G. N.; Murry, J. A.; Corley, E.; DiMichele, L.; Hughes, D. Org. Lett. 2006, 18, 3903.
35. Harrison, P.; Meek, G. Tetrahedron Lett. 2004, 45, 9277.
36. Brace, G. N.; Holmes, I. P. Synthesis 2005, 3229.
37. (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
38. (b) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567.
39. Burk, M. J.; Fraster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653.
40. Holz, J.; Zayas, O.; Jiao, H.; Baumann, W.; Spannenberg, A.; Monsees, A.; Riermeier, T. H.; Almena, J.; Kadyrov, R.; Börner, A. Chem. - Eur. J. 2006, 12, 5001.
41. (a) Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
42. (b) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
43. Miyazaki, T.; Sugaware, M.; Danjo, H.; Imamoto, T. Tetrahedron Lett. 2004, 45, 9341.
44. Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612.
45. Schlewer, G.; Krogsgaard-Larsen, P. Acta Chem. Scand., Ser. B 1984, B38, 815.