1088993-98-9Relevant articles and documents
Convergent kilogram-scale synthesis of dual orexin receptor antagonist
Girardin, Melina,Ouellet, Stephane G.,Gauvreau, Danny,Moore, Jeffrey C.,Hughes, Greg,Devine, Paul N.,O'Shea, Paul D.,Campeau, Louis-Charles
, p. 61 - 68 (2013/03/13)
MK-6096 is an orexin receptor antagonist in clinical trials for the treatment of insomnia. Herein we describe its first kilogram-scale synthesis. Chirality on the α-methylpiperidine core was introduced in a biocatalytic transamination using a three-enzyme system with excellent enantioselectivity (>99% ee). Low diastereoselectivity of the lactam reduction was overcome by development of a camphor sulfonic acid salt formation and dr upgrade. A chemoselective O-alkylation with 5-fluoro-2-hydroxypyridine was optimized and developed. Overall, 1.2 kg of MK-6069 was prepared in nine steps and 13% overall yield.
PROCESS FOR THE PREPARATION OF AN OREXIN RECEPTOR ANTAGONIST
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, (2009/12/27)
The present invention is directed to processes for preparing a pyridyl piperidine compound which is an antagonist of orexin receptors, and which is useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved.