Synthesis of a naphthyridone p38 MAP kinase inhibitor

JYL Chung, RJ Cvetovich, M McLaughlin…

Index: Cvetovich, Raymond J.; Reamer, Robert A.; DiMichele, Lisa; Chung, John Y. L.; Chilenski, Jennifer R. Journal of Organic Chemistry, 2006 , vol. 71, # 22 p. 8610 - 8613

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Citation Number: 19

Abstract

Compound 1 is a p38 MAP kinase inhibitor potentially useful for the treatment of rheumatoid arthritis and psoriasis. A novel six-step synthesis suitable for large-scale preparation was developed in support of a drug development program at Merck Research Laboratories. The key steps include a tandem Heck-lactamization, N-oxidation, and a highly chemoselective Grignard addition of 4-(N-tert-butylpiperidinyl) magnesium chloride to a naphthyridone N- ...