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Model reactions targeted at the synthesis of carbon‐14 labeled CI‐996, a potent antagonist of angiotensin II receptor (1)
Author(s) -
Ekhato I. Victor,
Huang Che C.
Publication year - 1994
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.2580340303
Subject(s) - chemistry , tetrazole , imidazole , methylene bridge , alkylation , mesylate , methylene , biphenyl , coupling reaction , stereochemistry , chemical synthesis , angiotensin ii , medicinal chemistry , combinatorial chemistry , organic chemistry , receptor , catalysis , in vitro , biochemistry
A reaction sequence suitable for the preparation of an analog of 2‐propyl‐1‐[2′‐(1H‐tetrazol‐5‐yl)[1,1′‐biphenyl]‐4‐yl]methyl‐4‐[2‐(trifluoroacetyl)‐1H‐pyrrol‐1‐yl]‐1H‐imidazole‐5‐carboxylic acid, with 14 C at the methylene bridge was developed. The would‐be labeled fragment (12) was derived from 4‐iodobenzenemethanol (6) , which itself was constructed from 1,4‐dibromobenzene by the application of silicon chemistry. Pd° catalyzed coupling of TBDMS protected 6 and a tetrazole borate 10 gave the compound 12 which upon further transformation to the mesylate 13 , N‐alkylated an imidazole to furnish target compound.