A Modified Approach to 2-(N-Aryl)-1,3-oxazoles: Application to the Synthesis of the IMPDH Inhibitor BMS-337197 and Analogues

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2091-2093

  Dhar, T G Murali ^a   Guo, Junqing ^a   Shen, Zhongqi ^a   Pitts, William J ^a   Gu, Henry H ^a   Chen, Bang Chi ^a   Zhao, Rulin ^a   Bednarz, Mark S ^a   Iwanowicz, Edwin J ^a  

^a BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BMS 337197; BMS-337197; ENZYME INHIBITOR; INOSINATE DEHYDROGENASE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

ENZYME INHIBITORS; IMP DEHYDROGENASE; OXAZOLES;

EID: 0037071922     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020073i     Document Type: Article

References (10)

1. Peshakova, L. S.; Kalcheva, V. B.; Simov, D. A. Chem. Heterocycl. Compd. 1982, 741-752.
2. Dhar, T. G. M.; Shen, Z.; Guo, J.; Liu, C.; Watterson, S. H.; Gu, H. H.; Pitts, W. J.; Fleener, C. A.; Rouleau, K.; Sherbina, N. Z.; Mcintyre, K. W.; Witmer, M.; Tredup, J. A.; Chen, B. C.; Zhao, R.; Bednarz, M. S.; Cheney, D.L.; MacMaster, J. F.; Miller, L. F.; Berry, K. K.; Harper, T. W.; Banish, J. C.; Hollenbaugh, D. L.; Iwanowicz, E. J. J. Med. Chem. 2002, 45, 2127-2130.
3. (a) Van Leusen, A. M.; Jeuring, H. J.; Wildeman, J.; Nispen van, P. J. M.S. J. Org. Chem. 1981, 2069-2072.
4. (b) Froyen, P. Phosphorous, Sulfur Silcon Relat. Elem. 1991, 60, 81-84.
5. (c) Molina, P.; Fresneda, P. M.; Almendros, P. Synthesis 1993, 54-56.
6. (d) Fukushima, K.; Ibata, T. Heterocycles 1995, 149-154.
7. Armistead, D. M.; Badia, M. C.; Bemis, G. W.; Bethiel, R. S.; Frank, C. A.; Novak, P. M.; Ronkin, S. M.; Saunders: J. O. Patent WO9740028, 1997.
8. + 490.2091, found 490.2087.
9. Although we did not experience any explosions while doing this reaction at 90 °C in dioxane, extreme care should be exercised while heating an azide solution because of the possibility of explosions.
10. All compounds were of >98% purity by LC/MS and analytical HPLC systems.