Process development and pilot-scale synthesis of new cyclization conditions of substituted phenylacetamides to tetrahydroisoquinoline-2-ones using Eaton's reagent

Organic Process Research and Development

Volumn 14, Issue 1, 2010, Pages 225-228

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

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77149175417     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op9002533     Document Type: Article

References (23)

1. For general reviews see: (a) Wenner, W. J. Med. Chem. 1965, 8, 125.
2. (b) Klutschko, S.; Blankley, C. J.; Fleming, R. W.; Hinkley, J. M.; Werner, A. E.; Nordin, I.; Holmes, A.; Hoefle, M. L.; Cohen, D. M.; Essenburg, A. D.; Kaplan, H. R. J. Med. Chem. 1986, 29, 1953.
3. Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030.
4. Eaton, P. E.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071.
5. Farcasiu, D.; Cao, H. J. Mol. Catal. 1994, 87, 215.
6. Hansen, K. B.; Balsells, J.; Dreher, S.; Hsiao, Y.; Kubryk, M.; Palucki, M.; Rivera, N.; Steinhuebel, D.; Armstrong, J. D.; Askin, D.; Grabowski, E. J. J. Org. Process Res. Dev. 2005, 9, 634.
7. Zewge, D.; Chen, C. Y.; Deer, C.; Dormer, P. G.; Hughes, D. L. J. Org. Chem. 2007, 72, 4276.
8. Skalitzky, D. J.; Marakovits, J. T.; Maegley, K. A.; Ekker, A.; Yu, X. H.; Hostomsky, Z.; Webber, S. E.; Eastman, B. W.; Almassy, R.; Li, J. J. Med. Chem. 2003, 46, 210.
9. Dorow, R. L.; Herrinton, P. M.; Hohler, R. A.; Maloney, M. T.; Mauragis, M. A.; McGhee, W. E.; Moeslein, J. A.; Strohbach, J. W.; Veley, M. F. Org. Process Res. Dev. 2006, 10, 493.
10. Pandit, C. R.; Polniaszek, R. P.; Thottathil, J. K. Synth. Commun. 2002, 32, 2427.
11. Zhao, D.; Hughes, D. L.; Bender, D. R.; DeMarco, A. M.; Reider, P. J. J. Org. Chem. 1991, 56, 3001.
12. Kano, S.; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Chem. Pharm. Bull. 1985, 33, 340.
13. Gala, D.; Dahanukar, V. H.; Eckert, J. M.; Lucas, B. S.; Schumacher, D. P.; Zavialov, I. A. Org. Process Res. Dev. 2004, 8, 754.
14. Chae, J.; Buchwald, S. L. J. Org. Chem. 2004, 69, 3336.
15. This purity was sufficient for the downstream chemistry; thus, further upgrade of product purity was not attempted.
16. Talanov, V. S.; Garmestani, K.; Regino, C. A. S.; Milenic, D. E.; Plascjak, P. S.; Waldmann, T. A.; Brechbiel, M. W. Nucl. Med. Biol. 2006, 33, 469.
17. Shapiro, S. L.; Parrino, V. A.; Freedman, L. J. Am. Chem. Soc. 1959, 81, 3728.
18. Chan, H. S.; Kuo, S. C.; Liu, S. C.; Liu, C. H.; Hsu, S. L. Cancer Lett. (Shannon, Ireland) 2002, 186, 211.
19. Hosseinzadeh, R.; Golchoubian, H.; Masoudi, M. J. Chin. Chem. Soc. (Taipei, Taiwan) 2008, 55, 649.
20. Misra, V. S.; Husain, M. I. J. Indian Chem. Soc. 1959, 36, 270.
21. IPC sample was prepared by quenching a sample of the reaction mixture into aqueous methylamine solution.
22. Molino, B. F.; Liu, S.; Guzzo, P. R.; Beck, J. P. U.S. Patent 7, 541, 357, 2009.
23. Tamura, Y.; Uenishi, J.; Maeda, H.; Choi, H.; Ishibashi, H. Synthesis 1981, 7, 534.