Development of a scaleable synthesis of a 3-aminopyrazinone acetamide thrombin inhibitor

Organic Process Research and Development

Volumn 8, Issue 2, 2004, Pages 192-200

  Ashwood, Michael S ^a   Alabaster, Ramon J ^a   Cottrell, Ian F ^a   Cowden, Cameron J ^b   Davies, Antony J ^a   Dolling, Ulf H ^b   Emerson, Khateeta M ^a   Gibb, Andrew D ^a   Hands, David ^a   Wallace, Debra J ^b   Wilson, Robert D ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [3 [[2,2 DIFLUORO 2 (2 PYRIDYL)ETHYL]AMINO] 6 CHLORO 2 OXOHYDROPYRAZINYL] N [3 FLUORO (2 PYRIDYL)METHYL]ACETAMIDE; 2 AMINOMETHYL 3 FLUOROPYRIDINE; 2,2 DIFLUORO 2 (2 PYRIDYL)ETHYLAMINE; CYANIDE; ETHYLAMINE; PYRIDINE DERIVATIVE; SODIUM AZIDE; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; STRUCTURE ANALYSIS;

EID: 11144353615     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0341420     Document Type: Article

References (18)

1. Burgey, C. J.; Robinson, K. A.; Lyle, T. A. et al. J. Med. Chem. 2003, 46, 461-473.
2. Cowden, C. J.; Cooper, V. B.; Rush, D. J.; Frech, R. Patent WO 2001092234.
3. Dolling, U. H.; Alabaster, R. J.; Ashwood, M. S.; Cottrell, I. F.; Cowden, C. J.; Davies, A. J.; Hands, D.; Wallace, D. J.; Wilson, R. D. Patent WO 2002046160.
4. Sakamoto, T.; Kaneda, S.-I.; Nishimura, S.; Yamanaka, H. Chem. Pharm. Bull. 1985, 33, 565-571.
5. Marsaia, F.; Gueguiner, G. Tetrahedron 1983, 39, 2009.
6. Lecomte, L.; Gueguiner, G.; Turck, A. French Patent 2 686 340, 1992.
7. Emerson, K. H.; Ashwood, M. S.; Hands, D.; Wilson, R. D.; Cottrell, I. F.; Brands, K. M. J. Synth. Commun. 2003, 33, 4231-4236.
8. Barriere, J.; Bacque, E.; Puchault, G.; Quenet, Y.; Molherat, C.; Cassayre, J.; Paris, J. Tetrahedron 1998, 54, 12859-12883.
9. Rhee, J.; Lim, J.; Im, W.; Yang, J. Bull. Korean Chem. Soc. 1993, 14 (4), 301-302.
10. Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048-7054.
11. Taguch, T.; Kitajawa, O.; Monkawa, T.; Nishiwaki, T.; Uehara, H.; Endo, H.; Kobayashi, Y. Tetrahedron Lett. 1986, 27, 6103-6106.
12. Sato, K.; Kawata, R.; Ama, F.; Omote, M.; Ando, A.; Kumadaki, I. Chem. Pharm. Bull. 1999, 47, 1013-1016.
13. Eto, H.; Kaneko, Y.; Sakamoto, T. Chem. Pharm. Bull. 2000, 48, 982-990.
14. Ashwood, M. S.; Cottrell, I. F.; Cowden, C. J.; Wallace, D. J.; Davies, A. J., Kennedy, D. J.; Dolling, U. H. Tetrahedron Lett. 2002, 43, 9271-73.
15. Jpn. Kokai Tokkyo Koho, 06219994 1994.
16. Cheeseman, G. W. H.; Freestone, A. J.; Godwin, R. A.; Hough, T. L. J. Chem. Soc., Perkin Trans. 1 1975, 1888-1891.
17. Fleitz, F. J.; Lyle, T. A.; Zheng, N.; Armstrong, J. D.; Volante, R. P. Synth. Commun. 2000, 30, 3171-3180.
18. Flakes of copper 1 μ thick with a very high surface area purchased from Sigma-Aldrich Chemical Co.