Theodore S. T. Wang, R. Fawwaz, R. Heertum
Apr 1, 1995
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Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
1-Methyl-4-[4-(7-chloro-4-quninolyl-[3- 14 C]-amino)-benzoyl]piperazine (V) was prepared for pharmacokinetic and pharmacodynamic evaluation. The synthesis of V was accomplished first by a modified Claisen ester condensation reaction of diethyl-[2- 14 C]-malonate, triethyl orthoformate, and acetic anhydride in the presence of ZnCl 2 to form ethyl ethoxymethylene-[2- 14 C]-malonate (1), which was further condensed with m-chloroaniline to yield 7-chloro-4-hydroxy-3-[ 14 C]-quinoline-ethyl-carboxylate (II). Saponification of II yielded the corresponding carboxylic acid (III). Decarboxylation of the acid group upon heating and a substitution of the 4-OH group of compound 111 into chlorine atom with POCl 3 produced 4,7-dichloro-[3- 14 C]-quinoline (IV), which then was reacted with 1 -methyl-4-(p-amino-benzoyl)piperazine to form the title compound V. There were a total of five steps of reaction, with a overall yield of 34.3%. The specific activity was 1,74 mCi/mmol