Premium
Synthesis of carbon‐14 labelled (3‐{[(Z)‐5‐chloro‐2,3‐dihydro‐3‐(hydroxy‐2‐thienylmethylene)‐2‐oxo‐1 H ‐indol‐1‐yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage‐targeted antirheumatic drug
Author(s) -
Giraud Isabelle,
Rapp Maryse,
Dupuy JeanMichel,
Maurizis JeanClaude,
Madelmont JeanClaude
Publication year - 2000
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/(sici)1099-1344(20000315)43:3<297::aid-jlcr317>3.0.co;2-#
Subject(s) - chemistry , chloride , yield (engineering) , indole test , carbonate , medicinal chemistry , thiophene , methylene , barium carbonate , carboxamide , nuclear chemistry , stereochemistry , organic chemistry , raw material , materials science , metallurgy
A [ 14 C]‐labelled form of (3‐{[(Z)‐5‐chloro‐2,3‐dihydro‐3‐(hydroxy‐2‐thienylmethyl‐ene)‐2‐oxo‐1 H ‐indol‐1‐yle]carbonylamino}propyl)trimethylammonium chloride, a potential cartilage‐targeted antirheumatic drug, was required for pharmcokinetic studies. This compound, labelled with [ 14 C] located in the C‐3 methylene position, was prepared in four steps starting from N ‐[3‐(dimethylamino)propyl]‐5‐chloro‐2,3‐dihydro‐2‐oxo‐1 H ‐indole‐1‐carboxamide and 2‐thiophene‐[ 14 C]carbonyl chloride, previously synthesized by a two‐step sequence from barium [ 14 C]‐carbonate and 2‐thienyllithium. The desired product was obtained with a specific activity of 359 MBq/mmol (9.7 mCi/mmol). The overall radiochemical yield was 50% based on barium [ 14 C]‐carbonate. Copyright © 2000 John Wiley & Sons, Ltd.