Convenient synthesis of 2-alkylamino-6-carboxy-5,7-diarylcyclopenteno[1,2- b]pyridines via direct acylamination with imidoyl chlorides

Tetrahedron

Volumn 61, Issue 14, 2005, Pages 3473-3481

  Takahashi, Hirobumi ^a   Fukami, Takehiro ^a   Kojima, Hisaki ^a   Yamakawa, Takeru ^a   Takahashi, Hiroyuki ^a   Sakamoto, Toshihiro ^a   Nishimura, Teruyuki ^a   Nakamura, Masayuki ^a   Yosizumi, Takashi ^a   Niiyama, Kenji ^a   Ohtake, Norikazu ^a   Hayama, Takashi ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Acylamination; Cyclopenteno 1,2 b pyridines; ETA antagonist; Imidoyl chloride

Indexed keywords

2 (1 BENZOYL 1 ISOPROPYLAMINO) 6 TERT BUTOXYCARBONYL 7 [2 (2 METHOXYCARBONYLPROPYL) 4 METHOXYPHENYL] 5 (3,4 METHYLENEDIOXYPHENYL) CYCLOPENTENO[1,2 B]PYRIDINE; 6 TERT BUTOXYCARBONYL 7 [2 (2 METHOXYCARBONYLPROPYL) 4 METHOXYPHENYL] 5 (3,4 METHYLENEDIOXYPHENYL)CYCLOPENTENO[1,2 B]PYRIDINE; 6 TERT BUTOXYCARBONYL 7 [2 (2 METHOXYCARBONYLPROPYL) 4 METHOXYPHENYL] 5 (3,4 METHYLENEDIOXYPHENYL)CYCLOPENTENO[1,2 B]PYRIDINE N OXIDE; 7 [2 (2 CARBOXYPROPYL) 4 METHOXYPHENYL] 5 (3,4 METHYLENEDIOXYPHENYL) 2 ISOPROPYLAMINOCYCLOPENTENO[1,2 B]PYRIDINE 6 CARBOXYLIC ACID; CHLORIDE; PYRIDINE 1 OXIDE; PYRIDINE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 20144379893     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.003     Document Type: Article

References (34)

1. M. Yanagisawa, H. Kurihara, S. Kimura, Y. Tomobe, M. Kobayashi, Y. Mitsui, Y. Yazaki, K. Goto, and T. Masaki Nature 332 1988 411 415
2. K. Hosoda, K. Nakao, H. Arai, O. Nagakawa, K. Hosoda, S. Suga, S. Nakanishi, and H. Imura FEBS Lett. 287 1991 23 26
3. A selective antagonist. (a) M. Winn, T.W. Geldern, T.J. Opgenorth, H. Jae, A.S. Tasker, S.A. Boyd, J.A. Kester, R.A. Mantei, R. Bal, B.K. Sorensen, J.R. Wu-Wong, W.J. Chiou, D.B. Dixon, E.I. Novosad, L. Hernadez, and K.C. Marsh J. Med. Chem. 38 1996 1039 1048
4. C. Wu, M.F. Chan, F. Stavros, I. Okun, S. Mong, K.M. Keller, T. Brock, T.P. Kogan, and R.A.F. Dixon J. Med. Chem. 40 1997 1690 1697
5. G. Liu, K.J. Henry Jr., B.G. Szczepankiewicz, M. Winn, N.S. Kozmina, S.A. Boyd, J. Wasicak, T.W. von Geldern, J.R. Wu-Wong, W.J. Chiou, D.B. Dixon, B. Nguyen, K.C. Marsh, and T.J. Opgenorth J. Med. Chem. 41 1998 3261 3275
6. P.C. Astles, T.J. Brown, F. Halley, C.M. Handscombe, N.V. Harris, T.N. Majid, C. McCarthy, A. McLay, B. Porter, A.G. Roach, C. Sargent, C. Smith, and R.J.A. Walsh J. Med. Chem. 43 2000 900 910
7. C. Wu, E.R. Decker, N. Blok, J. Li, A.R. Bourgoyne, H. Bui, K.M. Keller, V. Knowles, W. Li, F.D. Stavros, G.W. Holland, T.A. Brock, and R.A.F. Dixon J. Med. Chem. 44 2001 1211 1216
8. H. Morimoto, N. Ohashi, H. Shimadzu, E. Kushiyama, H. Kawanishi, T. Hosaka, Y. Kawase, K. Yasuda, K. Kikkawa, R. Yamauchi-Kohno, and K. Yamada J. Med. Chem. 44 2001 3369 3377
9. N. Ishizuka, K. Matsumura, K. Sakai, M. Fujimoto, S. Mihara, and T. Yamamori J. Med. Chem. 45 2002 2041 2055
10. N. Murugesan, Z. Gu, S. Spergel, M. Young, P. Chen, A. Mathur, L. Leith, M. Hermsmeier, E.C.-K. Liu, R. Zhang, E. Bird, T. Waldron, A. Marino, B. Koplowitz, W.G. Humphreys, S. Chong, R.A. Morrison, M.L. Webb, S. Moreland, N. Trippodo, and J.C. Barrish J. Med. Chem. 46 2003 125 137
11. B selective antagonist. (a) J.L. Balwierczak, C.W. Bruseo, D. Del Grande, A.Y. Jeng, P. Savage, and S.S. Shetty J. Cardiovasc. Pharmacol. 26 Suppl. 3 1995 S393 S396
12. M.F. Chan, A. Kois, E.J. Verner, B.G. Raju, R.S. Castillo, C. Wu, I. Okun, F.D. Stavros, and V.N. Balaji Bioorg. Med. Chem. 6 1998 2301 2316
13. G. Liu, N.S. Kozmina, M. Winn, T.W. von Geldern, W.J. Chiou, D.B. Dixon, B. Nguyen, K.C. Marsh, and T.J. Opgenorth J. Med. Chem. 42 1999 3679 3689
14. W.W.K.R. Mederski, M. Osswald, D. Dorsch, M. Christadler, C.-J. Schmitges, and C. Wilm Bioorg. Med. Chem. Lett. 9 1999 619 622
15. B balanced antagonist. (a) M. Clozel, V. Breu, G.A. Gray, B. Kalina, B. Loffler, K. Burri, J. Cassal, G. Hirth, M. Muller, W. Neidhart, and H. Ramuz J. Pharmacol. Exp. Ther. 270 1994 228 235
16. J.D. Elliot, M.A. Lago, R.D. Cousins, A. Gao, J.D. Leber, K.F. Erhard, P. Nambi, N.A. Elshourbagy, C. Kumar, J.A. Lee, J.W. Bean, C.W. Debrosse, D.S. Eggleston, D.P. Brooks, G. Feuerstein, R.R. Ruffolo, J. Weinstock, J.G. Gleason, C.E. Peishoff, and E. Ohlstein J. Med. Chem. 37 1994 1553 1557
17. B balanced antagonist. (a) Clozel, M.; Breu, V.; Gray, G. A.; Kalina, B.; Loffler, B.; Burri, K.; Cassal, J.; Hirth, G.; Muller, M.; Neidhart, W.; Ramuz, H. J. Pharmacol. Exp. Ther. 1994, 270, 228-235. (b) Elliot, J. D.; Lago, M. A.; Cousins, R. D.; Gao, A.; Leber, J. D.; Erhard, K. F.; Nambi, P.; Elshourbagy, N. A.; Kumar, C.; Lee, J. A.; Bean, J. W.; Debrosse, C. W.; Eggleston, D. S.; Brooks, D. P.; Feuerstein, G.; Ruffolo, R. R.; Weinstock, J.; Gleason, J. G.; Peishoff, C. E.; Ohlstein, E. J. Med. Chem. 1994, 37, 1553-1557. (c) Walsh, T. F.; Fitch, K. J.; Chakravarty, P. K.; Williams, D. L.; Murphy, K. A.; Nolan, N. A.; O'Brien, J. A.; Lis, E. V.; Pettibone, D. J.; Kivlighn, S. D.; Gabel, R. A.; Zingaro, G. J.; Krause, S. M.; Siegl, P. K. S.; Clineschmidt, B. V.; Greenlee, W. J. Abstracts of American Chemical Society National Meeting, Washington, DC, August 21-25, 1994, American Chemical Society: Washington, DC, 1994; MEDI 145. (d) Jae, H.-S.; Winn, M.; Dixon, D. B.; Marsh, K. C.; Nguyen, B.; Opgenorth, T. J.; von Geldern, T. W. J. Med. Chem. 1997, 40, 3217-3227. (e) Amberg, W.; Hergenröder, S.; Hillen, H.; Jansen, R.; Kettschau, G.; Kling, A.; Klinge, D.; Raschack, M.; Riechers, H.; Unger, L. J. Med. Chem. 1999, 42, 3026-3032.
18. H.-S. Jae, M. Winn, D.B. Dixon, K.C. Marsh, B. Nguyen, T.J. Opgenorth, and T.W. von Geldern J. Med. Chem. 40 1997 3217 3227
19. W. Amberg, S. Hergenröder, H. Hillen, R. Jansen, G. Kettschau, A. Kling, D. Klinge, M. Raschack, H. Riechers, and L. Unger J. Med. Chem. 42 1999 3026 3032
20. K. Niiyama, H. Takahashi, T. Nagase, H. Kojima, Y. Amano, K. Katsuki, T. Yamakawa, S. Ozaki, M. Ihara, M. Yano, T. Fukuroda, M. Nishikibe, and K. Ishikawa Bioorg. Med. Chem. Lett. 12 2002 3041 3045
21. K. Niiyama, T. Mase, H. Takahashi, A. Naya, K. Katsuki, T. Nagase, S. Ito, T. Hayama, A. Hisaka, S. Ozaki, M. Ihara, M. Yano, T. Fukuroda, K. Noguchi, M. Nishikibe, and K. Ishikawa Bioorg. Med. Chem. 10 2002 2461 2470
22. R.A. Abramovitch, and G.M. Singer J. Am. Chem. Soc. 91 1969 5672 5673
23. R.A. Abramovitch, and R.B. Rogers Tetrahedron Lett. 22 1971 1951 1954
24. R.A. Abramovitch, and G.M. Singer J. Org. Chem. 39 1974 1795 1802
25. R.A. Abramovitch, and R.B. Rogers J. Org. Chem. 39 1974 1802 1807
26. R.A. Abramovitch, R.B. Rogers, and G.M. Singer J. Org. Chem. 40 1975 41 47
27. R.A. Abramovitch, and T.D. Bailey J. Heterocycl. Chem. 12 1975 1079 1080
28. R.A. Abramovitch, D.A. Abramovitch, and P. Tomasik J. Chem. Soc., Chem. Commun. 21 1979 956 957
29. R.A. Abramovitch, J. Pilski, A. Konitz, and P. Tomasik J. Org. Chem. 48 1983 4391 4393
30. Recently, one pot method for the generation of imidoyl chloride and in situ reaction with pyridine N-oxide was described. P.J. Manley, and M.T. Bilodeau Org. Lett. 4 2002 3127 3129
31. 3 solution, Scheme 5).
32. H. Takahashi, N. Ohtake, T. Sakamoto, T. Iino, N. Kawanishi, M. Nakamura, T. Yoshizumi, K. Niiyama, S. Ozaki, H. Okada, A. Kano, H. Takahashi, Y. Ishii, M. Okada, M. Saito, Y. Sawazaki, T. Hayama, and M. Nishikibe Bioorg. Med. Chem. Lett. 14 2004 1503 1507
33. T. Yoshizumi, H. Takahashi, N. Ohtake, H. Jona, Y. Sato, H. Kishino, T. Sakamoto, S. Ozaki, H. Takahashi, Y. Shibata, Y. Ishii, M. Saito, M. Okada, M. Okada, T. Hayama, and M. Nishikibe Bioorg. Med. Chem. 12 2004 2139 3150
34. J.C. Brindly, J.M. Caldwell, G.D. Meakins, S.J. Plackett, and Price J. Chem. Soc., Perkin Trans. 1 1987 1153 1158