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One-pot synthesis of 3-(1-methylethyl)-2-(4-methoxyphenyl)-3H-naphth-[1,2-d] [2-14C] imidazole

✍ Scribed by G. Odasso; E. Toja

Publisher
John Wiley and Sons
Year
1983
Tongue
French
Weight
137 KB
Volume
20
Category
Article
ISSN
0022-2135

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✦ Synopsis

A one-pot synthesis of 3-(l-methylethyl)-2-(4-methoxyphenyl)-3H-naphth [1,2-d] [ 2 -C] imidazole (i), a nonacidic antiinflammatory and analgesic agent, is described. The starting material, 2-isopropylamino-1-nitronaphthalene ( 3 ) was hydrogenated, the resulting diamine (4) reacted with p-[carbonyl-C] anisaldehyde and the intermediate imidazoline ( 5 ) finally dehydrogenated to give (1) in a radiochemical yield of 63.4% with a radiochemical purity > 99%. The labelled compound has been used in pharmacokinetics and metabolism studies.

(1, -Scheme I) is a novel nonacidic antiinflammatory and analgesic agent devoid of gastroulcerogenic effects .

The unlabelled compound was prepared on a large scale from 2-isopropylamino-lnitrosonaphthalene (2) through the route shown i n Scheme I (I). This method however is less suitable for preparing the labelled compound required for pharmacokinetics and metabolism studies. Indeed (21, in the solid state and at r o o m temperature, undergoes a rapid degradation to a number of unidentified compounds (1)

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