Development of a scalable synthesis of oxadiazole based S1P1 receptor agonists

Organic Process Research and Development

Volumn 17, Issue 4, 2013, Pages 666-671

  Lukin, Kirill ^a   Kishore, Vimal ^a   Gordon, Thomas ^a  

^a ABBVIE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXADIAZOLES; SCALABLE SYNTHESIS; TRIPHENYLPHOSPHINE OXIDE;

EID: 84876592417     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op300345v     Document Type: Article

References (14)

1. Matloubian, M.; Lo, C. J.; Cinamon, G.; Lesneski, M. J.; Xu, Y.; Brinkman, V.; Allende, M. L.; Proia, R. L.; Cyster, J. G. Nature 2004, 427, 355
2. Martini, S.; Peters, H.; Bohler, T.; Budde, K. Expert Opin. Invest. Drugs 2007, 16, 505
3. Demont, E. H.; Andrews, B. I.; Bit, R. A.; Campbell, C. A.; Cooke, J. W. B.; Deeks, N.; Desai, S.; Dowell, S. J.; Gaskin, P.; Gray, J. R. J.; Haynes, A.; Holmes, D. S.; Kumar, U.; Morse, M. A.; Osborne, G. J.; Panchal, T.; Patel, B.; Perboni, A.; Taylor, S.; Watson, R.; Witherington, J.; Willis, R. ACS Med. Chem. Lett. 2011, 2, 444
4. For additional detailes on the oxadiazole formation mechanism see: Ooi, N. S.; Wilson, D. S. J. Chem. Soc. Perkin Trans. 2 1980, 1792
5. Pipik, B.; Ho, G.-J.; Williams, J. M.; Conlon, D. A. Synth. Commun. 2004, 34, 1863
6. Jochims, J. C. In Comprehensive Heterocyclic Chemistry II, Stor, R. C., Ed.; Pergamon Press: Oxford, 1996; Vol. 4, pp 179-228.
7. Cyclization of acylamidoximes into oxadiazoles was also accomplished in the presence of tetrabutylammonium fluoride: Gangloff, A. R.; Litvak, J.; Shelton, E. J.; Sperandio, D.; Wang, V. R.; Rice, K. D. Tetrahedron Lett. 2001, 42, 1441
8. Dieckmann, A.; Beniken, S.; Lorenz, C. D.; Doltsinis, N. L.; Kiedrowski, G. Chem.-Eur. J. 2011, 17, 468
9. Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326
10. Liek, C.; Machnitzki, P.; Nickel, T.; Schenk, S.; Tepper, M.; Stelzer, O. Z. Naturforsch. 1999, 54, 1532
11. Holman, N. J.; Koser, S. PCT Int. Appl. 1998 WO 1998007724. See also: Practical Process Research and Development; 2 nd ed., Anderson, N., Ed.; Academic Press, 2012.
12. Jenkins, J.; Mitsunobu, O. In E.R.O.S., Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 8, pp 5379-5390.
13. Borgulya, J.; Bernauer, K. Synthesis 1980, 545
14. Rawson, D. J.; Swain, N. A. PCT Int. Appl. 2007, WO2007063391.