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The synthesis of the carbonyl‐ 14 C analog of zatosetron maleate, a potent, long‐acting, orally effective 5‐HT 3 receptor antagonist
Author(s) -
O'Ban Douglas D.,
Wheeler William J.
Publication year - 1991
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.2580290603
Subject(s) - chemistry , antagonist , medicinal chemistry , stereochemistry , chemical synthesis , d 1 , diketone , bicyclic molecule , receptor , in vitro , biochemistry
Endo ‐5‐chloro‐2,3‐dihydro‐2,2‐dimethyl‐N‐(8‐methyl‐8 ‐azabicyclo‐[3.2.1.]‐oct‐3‐yl‐7‐benzofurancarboxamide‐[carbonyl‐ 14 C] (Z)‐2‐butenedioate (zatosetron‐[ 14 C] maleate, 1 ), has been prepared from 5‐chloro‐7‐bromo‐2,3‐dihydro‐2,2‐dimethylbenzofuran ( 5 ) in four radiochemical steps with the reaction of 5 with K 14 CN/CuCN as the key step. The synthesis of 5 from 2‐bromo‐4‐chlorophenol is also outlined.