Premium
Synthesis of [ 14 C]‐labelled 3‐[N‐(4‐bromophenyl)carbamoyl]‐7‐chloro‐4‐hydroxycoumarin and 3‐[N‐[5‐(trifluoromethyl)‐1,3,4‐thiadiazol‐2‐yl]carbamoyl]‐7‐chloro‐4‐hydroxycoumarin
Author(s) -
Lee Byung H.,
Clothier Michael F.
Publication year - 1993
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.2580330905
Subject(s) - chemistry , 4 hydroxycoumarin , trifluoromethyl , malonate , chloride , medicinal chemistry , aniline , diethyl malonate , stereochemistry , organic chemistry , catalysis , alkyl
The novel [ 14 C]‐labelled 3‐carbamoyl‐4‐hydroxycoumarins were prepared in two steps from 4‐chloro‐acetylsalicyloyl chloride ( 3 ). The isotope was incorporated by the reaction of diethyl malonate‐1,3‐ 14 C with 4‐chloro‐acetylsalicyloyl chloride ( 3 ). Subsequent condensation of the resulting 3‐ethoxycarbonyl‐4‐hydroxy‐7‐chlorooumarin ( 5a ) with 4‐bromo‐aniline gave 3‐[N‐(4‐bromophenyl)carbamoyl‐7]‐chloro‐4‐hydroxycoumarin ( 1a ) with a specific activity of 0.7 mCi/mmol. Condensation of ( 5a ) with 2‐amino‐5‐trifluoromethyl‐1,3,4‐thiadiazole gave 3‐[N‐[5‐(trifluoromethyl)‐1,3,4‐thiadiazol‐2‐yl]carbamoyl]‐7‐chloro‐4‐ hydroxycoumarin ( 2a ) with a specific activity of 0.6mCi/mmol.