Synthesis of [carbonyl-14C]- and (methoxy-d3)-labeled N-[(2RS, 3RS)-1-benzyl-2-methyl-3-pyrrolidinyl] −5-chloro-2-methoxy-4-(methylamino) benzamide (YM-09151-2). A new potent neuroleptic agent

✍ Scribed by Kazuharu Tamazawa; Hideki Arima

• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: French
• Weight: 485 KB
• Volume: 21
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580210507

✦ Synopsis

Abstract

A new potent neuroleptic agent YM‐09151‐2, N‐[(2RS, 3RS)‐1‐benzyl‐2‐methyl‐3‐pyrrolidinyl]‐5‐chloro‐2‐methoxy‐4‐ (methylamino) benzamide (10c), was labeled with carbon‐14 and deuterium for biochemical studies such as metabolism and 14 pharmacokinetics. The synthesis of [carbonyl‐^14^C]YM‐09151‐2 (10a) from 4‐amino‐2‐hydroxy‐[carboxyl‐^14^C] benzoic acid (1a) in six stages is described. Overall radiochemical yield was 79.1% at a specific activity of 21.18 mCi/mmol. (Methoxy‐d~3~)YM‐09151‐2 (10b) was prepared from methyl 2‐(methoxy‐d~3~)‐4‐(N‐methyl‐N‐tosylamido) benzoate (5b) which was obtained by the reaction of methyl 2‐hydroxy‐4‐(N‐methyl‐N‐tosylamido) benzoate (4c) with iodomethane‐d~3~. Overall yield of 10b was 60.8% from iodomethane‐d~3~.