Premium
Preparation of carbon‐14 labeled N‐(2‐ethyl‐3‐chloro‐4‐pyridinyl)‐4‐(4‐chlorophenoxy)phenylacetamide
Author(s) -
Pearson N. R.
Publication year - 1998
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(199802)41:2<151::aid-jlcr64>3.0.co;2-r
Subject(s) - chemistry , amine gas treating , amination , ammonia , organic chemistry , reductive amination , transformation (genetics) , medicinal chemistry , stereochemistry , catalysis , biochemistry , gene
A 4‐step modified route has been developed for the synthesis of N‐(2‐ethyl‐3‐chloro‐4‐pyridinyl‐2‐[ 14 C])‐4‐(4‐chlorophenoxy)phenylacetamide ([ 14 C]‐ 1 ). The key transformation in the sequence is an amination/cyclization pair of reactions that furnished 2‐[ 14 C]‐4‐amino‐2‐ethylpyridine ( 4 ) from 5‐[ 14 C]‐1‐methoxyhept‐1‐en‐3‐yn‐5‐one ( 3 ) and ammonia. Amine 4 was then selectively chlorinated to provide 2‐[ 14 C]‐4‐amino‐3‐chloro‐2‐ethylpyridine ( 5 ) which was then coupled with 4‐(4‐chlorophenoxy)phenylacetic ethylformic anhydride ( 6 ) in a reaction mediated by trimethylaluminum to furnish the desired, radiolabeled phenylacetamide [ 14 C]‐ 1 . © 1998 John Wiley & Sons, Ltd.