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Synthesis of N ‐(2‐chloro‐5‐methylthiophenyl)‐ N ′‐(3‐methyl‐thiophenyl)‐ N ′‐[ 3 H 3 ]methylguanidine, {[ 3 H 3 ]CNS‐5161}
Author(s) -
Gibbs Andrew R.,
Morimoto Hiromi,
VanBrocklin Henry F.,
Williams Philip G.,
Biegon Anat
Publication year - 2002
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.561
Subject(s) - cyanamide , chemistry , yield (engineering) , guanidine , hydrochloride , sodium hydride , high performance liquid chromatography , tritium , sodium , medicinal chemistry , organic chemistry , materials science , metallurgy , physics , nuclear physics
Abstract The preparation of the title compound, [ 3 H 3 ]CNS‐5161, was accomplished in three steps starting with the production of [ 3 H 3 ]iodomethane (CT 3 I). The intermediate N ‐[ 3 H 3 ]methyl‐3‐(thiomethylphenyl)cyanamide was prepared in 77% yield by the addition of CT 3 I to 3‐(thiomethylphenyl)cyanamide, previously treated with sodium hydride. Reaction of this tritiated intermediate with 2‐chloro‐5‐thiomethylaniline hydrochloride formed the guanidine compound [ 3 H 3 ]CNS‐5161. Purification by HPLC gave the desired labeled product in an overall yield of 9% with >96% radiochemical purity and a final specific activity of 66 Ci mmol −1 . Copyright © 2002 John Wiley & Sons, Ltd.