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Convergent synthesis of two 14 C‐labeled β 3 ‐adrenergic receptor agonists
Author(s) -
Czeskis Boris A.,
Wheeler William J.,
Clodfelter Dean K.
Publication year - 2006
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.1086
Subject(s) - chemistry , potassium cyanide , amide , cyanation , amine gas treating , hydrogen peroxide , cyanide , stereochemistry , combinatorial chemistry , agonist , chemical synthesis , receptor , medicinal chemistry , organic chemistry , biochemistry , catalysis , in vitro
The synthesis of β 3 ‐adrenergic receptor agonists A and B with radiolabeled amide fragment, required for drug disposition studies, was accomplished based on initial formation of 2‐(4‐(2‐amino‐2‐methylpropyl)phenoxy)‐5‐[ 14 C]‐cyanopyridine by the reaction of 2‐bromo‐5‐iodopyridine with para ‐substituted phenol, and following cyanation of aromatic iodide with potassium cyanide‐[ 14 C]. After the coupling of the resulted amine with glycidyl derivatives of 4‐hydroxyindole and 4‐hydroxycarbazole, the corresponding nitriles were hydrolyzed with basic hydrogen peroxide to obtain target amides A and B . Copyright © 2006 John Wiley & Sons, Ltd.