Development and scale-up of an optimized route to the ALK inhibitor CEP-28122

Organic Process Research and Development

Volumn 16, Issue 1, 2012, Pages 148-155

  Allwein, Shawn P ^a   Roemmele, Renee C ^a   Haley, James J ^a   Mowrey, Dale R ^a   Petrillo, Daniel E ^a   Reif, James J ^a   Gingrich, Diane E ^b   Bakale, Roger P ^a  

^a Cephalon Inc   (United States)

^b CEPHALON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANAPLASTIC LYMPHOMA KINASE; BIOLOGICAL SCREENING; ENZYMATIC RESOLUTIONS; HYDROCHLORIDE SALTS; IN-SITU; MEDICINAL CHEMISTRY; NITRO-GROUP REDUCTIONS; ONE POT; OPTIMIZED PROCESS; REDUCTIVE AMINATION; RESEARCH AND DEVELOPMENT; SCALE-UP; TO EFFECT; TRANSFER HYDROGENATIONS;

BIOLOGY; NITRATION;

OPTIMIZATION;

EID: 84856155968     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200313v     Document Type: Article

References (20)

1. Morris, S. W.; Kirstein, M. N.; Valentine, M. B.; Dittmer, K. G.; Shapiro, D. N.; Saltman, D. L.; Look, A. T. Science 1994, 263, 1281-1284
2. Grande, E.; Bolos, M.; Arriola, E. Mol. Cancer Ther. 2011, 10 (4) 569-571
3. Shaw, A. T.; Solomon, B. Clin. Cancer Res. 2011, 17, 2081-2086
4. Mosse, Y. P.; Wood, A.; Maris, J. M. Clin. Cancer Res. 2009, 15, 5608-5614
5. Gingrich, D. E.; Lisko, J. G.; Curry, M. A.; Cheng, M.; Quail, M.; Albom, M. S.; Angeles, T. S.; Aimone, L. D.; Haltiwanger, R. C.; Wells-Knecht, K.; Ott, G. R.; Ator, M. A.; Ruggeri, B.; Dorsey, B. D. J. Med. Chem. Submitted for publication.
6. Kraus, G. A.; Choudhury, P. K. J. Org. Chem. 2002, 67, 5857-5859
7. Yoshii, F.; Nakamura, T.; Hirono, S.; Shimizu, Y.; Hoshi, T.; Ando, M.; Hagiwara, H. Helv. Chim. Acta 2001, 84, 2051-2063
8. Chandrasekhar, S.; Babu, B. N.; Prabhakar, A.; Sudhakar, A.; Reddy, M. S.; Kiran, M. U.; Jagadeesh, B. Chem. Commun. 2006, 14, 1548-1550
9. Ott, G. R.; Tripathy, R.; Cheng, M.; McHugh, R.; Anzalone, A. V.; Underiner, T. L.; Curry, M. A.; Quail, M. R.; Lu, L.; Wan, W.; Angeles, A. S.; Albom, A. S.; Aimone, L. D.; Ator, M. A.; Ruggeri, B. A.; Dorsey, B. D. ACS Med. Chem. Lett. 2010, 1, 493-498
10. Goldberg, Y.; Bensimon, C.; Alper, H. J. Org. Chem. 1992, 57, 6374-6376
11. Goldberg, Y.; Alper, H. J. Org. Chem. 1993, 58, 3072-3075
12. Watson, W. D. J. Org. Chem. 1985, 50, 2145-2148
13. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491-3494
14. Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129-170
15. Moriconi, E. J.; Crawford, W. C. J. Org. Chem. 1968, 33, 370-378
16. Forro, E.; Fülöp, F. Tetrahedron: Asymmetry 2004, 15, 573-575
17. Forro, E.; Fülöp, F. Tetrahedron: Asymmetry 2004, 15, 2875-2880
18. Kirk, O.; Christensen, M. W. Org. Process Res. Dev. 2002, 6, 446-451
19. Argade, A. Chemoenzymatic synthesis of stereoisomerically enriched β-lactams using lipase B. U.S. Patent 7,459,301 B2, December 2, 2008
20. Chem. Abstr. 2006, 144, 487353.