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Synthesis of N‐(3‐azido‐4‐chlorophenyl)‐N′‐[ 3 H‐methyl] thiourea, an efficient photoaffinity probe for the urea carrier
Author(s) -
Lamotte Herve,
Degeilh Francoise,
Neau Philippe,
Ripochet Pierre,
Rousseau Bernard
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.2580340312
Subject(s) - chemistry , methylamine , thiourea , urea , medicinal chemistry , sodium acetate , nuclear chemistry , organic chemistry
Starting from commercial 4‐chloro‐3‐nitroaniline, through a 5 step synthesis, was prepared 3‐azido‐4‐chlorophenylisothiocyanate 5 which was reacted with [ 3 H]‐methylamine. The latter was obtained by three methods: i‐ [ 3 H]‐LiAlT 4 reduction of benzylcarbamate gave rise to [ 3 H]‐methylamine (S.A.: >70 Ci/mmol). ii‐ Catalytic reduction of HCN with 3 H 2 lead to [ 3 H]‐CH 3 NH 2 (S.A.: 0.7 Ci/mmol). iii‐ Schmidt rearrangement of [ 3 H]‐sodium acetate gave [ 3 H]‐CH 3 NH 2 (S.A.: 29 Ci/mmol).Compound 7 at the highest specific activity had a self radiolysis rate precluding its practical use in biological studies whilst 29 Ci/mmol [ 3 H]‐7 was satisfactory.