Improved synthesis of 3-substituted-4-amino-[3,2-c]-thienopyridines

Journal of Organic Chemistry

Volumn 74, Issue 10, 2009, Pages 3849-3855

  Engstrom, Kenneth M ^a   Baize, Amanda L ^a   Franczyk, Thaddeus S ^a   Kallemeyn, Jeffrey M ^a   Mulhern, Mathew M ^a   Rickert, Robert C ^a   Wagaw, Seble ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; HIGH TEMPERATURE; REDUCTIVE CYCLIZATION;

AMINATION; AMINES; CHEMICAL COMPOUNDS; CYANIDES; FRIEDEL-CRAFTS REACTION;

SYNTHESIS (CHEMICAL);

4 AMINO[3,2 C]THIENOPYRIDINE; ALKENE DERIVATIVE; AZIDE; NITRILE; THIENOPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; FRIEDEL CRAFTS REACTION; REACTION OPTIMIZATION; REDUCTION; SUBSTITUTION REACTION; TEMPERATURE;

CARBON DIOXIDE; CYCLIZATION; HALOGENS; METALS; OXIDATION-REDUCTION; PYRIDINES; THIOPHENES;

EID: 65949097064     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9003772     Document Type: Article

References (29)

1. Litvinov, V. P.; Dotsenko, V. V.; Krivokolysko, S. G. Adv. Het. Chem. 2007, 93, 117-178.
2. Heyman, H. R.; Frey, R. R.; Bousquet, P. F.; Cunha, G. A.; Moskey, M. D.; Ahmed, A. A.; Soni, N. B.; Marcotte, P. A.; Pease, L. J.; Glaser, K. B.; Yates, M.; Bouska, J. J.; Albert, D. H.; Black-Schaefer, C. L.; Dandliker, P. J.; Stewart, K. D.; Rafferty, P.; Davidsen, S. K.; Michaelides, M. R.; Curtin, M. L. Bioorg. Med. Chem. Lett. 2007, 17, 1246-1249.
3. For a review on the synthesis of thienopyridines, see ref 1. Barker, J. M. Adv. Heterocycl. Chem. 1977, 21, 65-118.
4. (a) Ikeura, Y.; Tanaka, T.; Kiyota, Y.; Morimoto, S.; Ogina, M.; Ishimaru, T.; Kamo, I.; Doi, T.; Natsugari, H. Chem. Pharm. Bull. 1997, 45, 1642-1652.
5. (b) Molina, P.; Fresneda, P. M.; Hurtado, F. Synthesis 1987, 1, 45-48.
6. (c) Farnier, M.; Soth, S.; Fournari, P. Can. J. Chem. 1976, 54, 1066-1073.
7. (a) New, J. S.; Christopher, W. L.; Yevich, J. P.; Butler, R.; Schlemmer, R. F.; VanderMaelen, C. P.; Cipollina, J. A. J. Med. Chem. 1989, 32, 1147-1156.
8. (b) Eloy, F.; Deryckere, A. Bull. Soc. Chim. Belges 1970, 79, 301-312.
9. For the use of catalytic iodine to lower the isomerization reaction temperature, see: (a) Miyazaki, Y.; Nakano, M.; Sato, H.; Truesdale, A. T.; Stuart, J. D.; Nartey, E. N.; Hightower, K. E.; Kane-Carson, L. Bioorg. Med. Chem. Lett. 2007, 17, 250-254.
10. For the use of tributylamine as an additive, see: (a) Abbott, L.; Betschmann, P.; Burchat, A.; Calderwood, D. J.; Davis, H.; Hrnciar, P.; Hirst, G. C.; Li, B.; Morytko, M.; Mullen, K.; Yang, B. Bioorg. Med. Chem. Lett. 2007, 17, 1167-1171.
11. (a) Wikel, J. H.; Denney, M. L.; Vasileff, R. T. J. Heterocyclic Chem. 1993, 30, 289-290.
12. (b) Herz, W.; Tsai, L. J. Am. Chem. Soc. 1953, 75, 5122-5123.
13. Gronowitz, S.; Timari, G. J. Het. Chem. 1990, 27, 1127-1129.
14. Beaton, H.; Hamley, P.; Tinker, A. C. Tetrahedron Lett. 1998, 39, 1227-1230.
15. (a) Steinkopf, W.; Jacob, H.; Penz, H. Just. Leib. Ann. Der Chem. 1934, 512, 136-156.
16. (b) Lawesson, S. Ark. Kemi 1957, 11, 325-336.
17. (c) Hawkins, D. W.; Iddon, B.; Longthorne, D. S.; Rosyk, P. J. J. Chem. Soc. Perkin Trans. 1 1994, 19, 2735-2744.
18. For a one-step synthesis of 13 from 3,4-dibromothiophene using copper (I) cyanide, see: Gonzalez, I. C.; Davis, L. N.; Smith, C. K. Bioorg. Med. Chem. Lett. 2004, 14, 4037-4043.
19. For a three-step synthesis of 13 from 3,4-dibromothiophene involving dehydration of 4-bromothiophene-3-carbaldehyde oxime, see: Fournari, P.; Guillard, R.; Person, M. Bull. Chim. Soc. Fr. 1967, 11, 4115-4120.
20. Kametani, T.; Yamanaka, T.; Ogasawara, K. J. Chem. Soc. C 1969, 385-387.
21. Gowda, D. C.; Mahesh, B.; Gowda, S. Indian J. Chem. 2001, 40B, 75-77.
22. (a) Hamid, A.; Elomri, A.; Daich, A. Tetrahedron Lett. 2006, 47, 1777-1781.
23. (b) Wang, Y. D.; Boschelli, D. H.; Johnson, S.; Honores, E. Tetrahedron 2004, 60, 2937-2942.
24. (c) Althius, T. H.; Kadin, S. B.; Czuba, L. J.; Moore, P. F.; Hess, H. J. J. Med. Chem. 1980, 23, 262-269.
25. Ranu, B. C.; Sarkar, A.; Guchhait, S. K.; Ghosh, K. J. Indian Chem. Soc. 1998, 75, 690-694.
26. For reduction of α,β-unsaturated nitroalkenes to aldoximes using tin (II) chloride, see: Kabalka, G. W.; Goudgaon, N. M. Synth. Commun. 1988, 18, 693-697.
27. Compagnone, R. S.; Suarez, A. I.; Zambrano, J. L.; Pina, I. C.; Dominguez, J. N. Synth. Commun. 1997, 27, 1631-1641.
28. Siegrist, U.; Baumeister, P.; Blaser, H.-U.; Studer, M.; The Selective Hydrogenation of Functionalized Nitroarenes: New Catalytic Systems. In Catalysis of Organic Reactions; Herkes, F. E., Ed. Marcel Dekker, Inc.: New York, 1998; Vol 75, pp 207-219.
29. 2 systems is currently under investigation and will be reported in due course.