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13C- and 14C-labelling of N-[1-(4-chlorophenyl)-1H-pyrrol-2-yl-methyleneamino] guanidinium acetate

✍ Scribed by Maria Almeida; Petra Johannesson; Arne Boman; Torbjörn Lundstedt

Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
101 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

N‐[1‐(4‐chlorophenyl)‐1H‐pyrrol‐2‐yl‐^13^C~4~‐methyleneamino]guanidinium acetate has been synthesized by a four‐step procedure. This involved reduction of the Weinreb amide N,N′‐dimethyl‐N,N′‐dimethyloxybutane‐1,4‐diamide‐1,2,3,4‐^13^C~4~ by Dibal‐H to give the corresponding unstable dialdehyde which is reacted in situ with 4‐chloroaniline to form 1‐(4‐chlorophenyl)‐1H‐pyrrole‐^13^C~4~. This pyrrole analogue underwent a Vilsmeyer acylation with POCl~3~/DMF followed by final reaction with aminoguanidine bicarbonate to produce the desired labelled compound with 99% atom ^13^C. By using DMF [α‐^14^C] a radio‐labelled analogue was synthesized with a specific activity of 60 mCi/mmol. Copyright © 2005 John Wiley & Sons, Ltd.

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