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Adventures in Atropisomerism: Synthesis of a Reversible BTK Inhibitor and Ventures Into Ni Catalysis

Date: 
Tuesday, January 29, 2019 - 12:45 to 14:00
Speaker: 
Dr. Steven Wisniewski
Affiliation: 
Chemical and Synthetic Development, Bristol Meyer Squibb
Event Category: 
LMC - Lectures in Modern Chemistry
Location: 
Chemistry B250

Abstract:

BMS-986142-01, currently in clinical studies for the treatment of immunological diseases as a reversible inhibitor of the BTK enzyme, is a molecularly complex active pharmaceutical ingredient (API) due to the atypical presence of two atropisomeric bonds and an asymmetric tertiary alcohol, resulting in eight possible diastereomers. Because the higher energy C-C atropisomeric bond has a lowered risk of isomerization under 90 °C and most chemical conditions, setting this chiral axis first would serve as a chiral template for the lower energy C-N atropisomeric bond, thereby enabling a robust and efficient route to BMS-986142-01 with complete diastereomeric and enantiomeric control.