An Efficient, Direct Bis-ortho-chlorination of 4-(Difluoromethoxy) aniline and Its Application to the Synthesis of BMS-665053, a Potent and Selective Pyrazinone- …

J Li, D Smith, S Krishnananthan, RA Hartz…

文献索引：Li, Jianqing; Smith, Daniel; Krishnananthan, Subramaniam; Hartz, Richard A.; Dasgupta, Bireshwar; Ahuja, Vijay; Schmitz, William D.; Bronson, Joanne J.; Mathur, Arvind; Barrish, Joel C.; Chen, Bang-Chi Organic Process Research and Development, 2012 , vol. 16, # 1 p. 156 - 159

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被引用次数: 4

摘要

An efficient scale-up synthesis of (S)-5-chloro-1-(1-cyclopropylethyl)-3-(2, 6-dichloro-4- (difluoromethoxy) phenylamino)-pyrazin-2 (1 H)-one, 1 (BMS-665053), is described. This new process features a one-step direct bis-ortho-chlorination of 4-(difluoromethoxy) aniline with HCl and H2O2, and a palladium-catalyzed coupling of 2, 6-dichloro-4-(difluoromethoxy) aniline 2 and (S)-3, 5-dichloro-1-(1-cyclopropylethyl) pyrazin-2 (1 H)-one 3. The process ...