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Synthesis of [carbonyl‐ 14 C]‐ and (methoxy‐d 3 )‐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
Author(s) -
Tamazawa Kazuharu,
Arima Hideki
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210507
Subject(s) - benzamide , chemistry , yield (engineering) , benzoic acid , carbon 14 , metabolism , stereochemistry , metabolite , chemical synthesis , medicinal chemistry , organic chemistry , in vitro , biochemistry , materials science , physics , quantum mechanics , metallurgy
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 .