Initial process development and scale-up of the synthesis of a triple reuptake inhibitor ALB 109780

Organic Process Research and Development

Volumn 16, Issue 3, 2012, Pages 499-506

  Yang, Qiang ^a   Ulysse, Luckner G ^a   McLaws, Mark D ^a   Keefe, Daniel K ^a   Haney, Brian P ^a   Zha, Congxiang ^a   Guzzo, Peter R ^a   Liu, Shuang ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; CORE STRUCTURE; INITIAL PROCESS; MORPHOLINES; PALLADIUM-CATALYZED; PROCESS DEVELOPMENT; SCALE-UP; SIDE PRODUCTS;

CYCLIZATION;

EID: 84863364431     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op3000064     Document Type: Article

References (23)

1. The World Health Organization. The World Health Report 2004:Changing History, Annex Table 3: Burden of disease in DALYs by cause,sex, and mortality stratum in WHO regions, estimates for 2002. Geneva: WHO, 2004.
2. Kessler, R. C.; Chiu, W. T.; Demler, O.; Walters, E. E. Arch. Gen. Psychiatry 2005, 62 (6) 617
3. Greenberg, P. E.; Kessler, R. C.; Birnbaum, H. G.; Leong, S. A.; Lowe, S. W.; Berglund, P. A.; Corey-Lisle, P. K. J. Clin. Psychiatry (Memphis, TN U.S.) 2003, 64 (12) 1465
4. Walter, M. W. Drug Dev. Res. 2005, 65, 97
5. Liu, S.; Molino, B. F. Annu. Rep. Med. Chem. 2007, 42, 13
6. DAquila, P. S.; Collu, M.; Gessa, G. L.; Serra, G. Eur. J. Pharmacol. 2000, 405, 365
7. Molino, B. F.; Liu, S.; Guzzo, P. R.; Beck, J. P. U.S. Patent 7,541,357, 2009.
8. Ulysse, L. G.; Yang, Q.; McLaws, M. D.; Keefe, D. K.; Guzzo, P. R.; Haney, B. P. Org. Process Res. Dev. 2010, 14, 225
9. Yang, Q.; Ulysse, L. G.; McLaws, M. D.; Keefe, D. K.; Guzzo, P. R.; Haney, B. P. Org. Synth. 2012, 89, 44
10. Hu, M.; Guzzo, P. R.; Zha, C.; Nacro, K.; Yang, Y.-L.; Hassler, C.; Liu, S. Tetrahedron Lett. 2012, 53, 846
11. Christensen, H.; Kiil, S.; Dam-Johansen, K.; Nielsen, O.; Sommer, M. B. Org. Process Res. Dev. 2006, 10, 762
12. Christensen, H.; Kiil, S.; Dam-Johansen, K.; Nielsen, O. Org. Process Res. Dev. 2007, 11, 956
13. Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742
14. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
15. Calkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234
16. Hamada, T.; Chieff, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124 (7) 1261
17. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195
18. Grasa, G. A.; Colacot, T. J. Org. Process Res. Dev. 2008, 12, 522
19. Lim, J. O.; Jin, M. K.; Ryu, H. C.; Kang, D. W.; Lee, J.; Pearce, L. V.; Tran, R.; Toth, A.; Blumberg, P. M. Eur. J. Med. Chem. 2009, 44, 322
20. Lee, J.; Kim, J. Y.; Song, K. S.; Kim, J.; Ahn, K. W.; Kong, Y. PCT Int. Appl. 2011014003, 2011.
21. Robinson, D. I. Org. Process Res. Dev. 2010, 14, 946
22. Snodin, D. J. Org. Process Res. Dev. 2010, 14, 960
23. Teasdale, A.; Delaney, E. J.; Eyley, S. C.; Jacq, K.; Taylor-Worth, K.; Lipczynski, A.; Hoffmann, W.; Reif, V.; Elder, D. P.; Facchine, K. L.; Golec, S.; Oestrich, R. S.; Sandra, P.; David, F. Org. Process Res. Dev. 2010, 14, 999