Selection of an Enantioselective Process for the Preparation of a CGRP Receptor Inhibitor

…, D Lin, RL Parsons, Y Pendri, RB Nielsen…

Index: Cann, Reginald O.; Chen, Chung-Pin H.; Gao, Qi; Hanson, Ronald L.; Hsieh, Daniel; Li, Jun; Lin, Dong; Parsons, Rodney L.; Pendri, Yadagiri; Nielsen, R. Brent; Nugent, William A.; Parker, William L.; Quinlan, Sandra; Reising, Nathan P.; Remy, Brenda; Sausker, Justin; Wang, Xuebao Organic Process Research and Development, 2012 , vol. 16, # 12 p. 1953 - 1966

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Citation Number: 6

Abstract

(R)-N-(3-(7-Methyl-1 H-indazol-5-yl)-1-(4-(1-methylpiperidin-4-yl) piperazine-1-yl)-1- oxopropan-2-yl)-4-(2-oxo-1, 2-dihydroquinolin-3-yl) piperidine-1-carboxamide (1) is a potent calcitonin gene-related peptide (CGRP) receptor antagonist. We have developed a convergent, stereoselective, and economical synthesis of the hydrochloride salt of 1 and demonstrated the synthesis on a multikilogram scale. Two different routes to the chiral ...