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Synthesis of [3H]CI-980, ethyl[5-anino-1,2-dihydro-2(S)-methyl-3(3-[3H]phenyl)pyrido[3,4-b]jpyrazin-7-YL] carbamate isethionate salt, a tubulin-binding, antimitotic, broad-spectrum antitumor agent

✍ Scribed by Helen T. Lee; Peter W. K. Woo

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
226 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

[^3^H]CI‐980 (10b) was synthesized in an eight‐step sequence with an overall yield of 2.4%. Reaction of m‐bromophenyl lithium (2) with N‐ethoxycarbonyl‐L‐alanine gave the chiral ketone 3. Reduction of 3 with sodium borohydride followed by alkaline N‐deprotection and condensation with ethyl 6‐amino‐4‐chloro‐5‐nitro‐2‐pyridine carbamate (6) gave 7. Chromium trioxide oxidation of 7 followed by reductive cyclization with iron‐acetic acid gave the key bromo intermediate 9. Palladium catalyzed ^3^H‐hydrogenolysis of 9 gave the free base form of [^3^H]CI‐980 (10a), which was converted to the isethionate salt (10b) before use.

📜 SIMILAR VOLUMES

Synthesis of [14C]CI-980, ethyl [5-amino
Synthesis of [14C]CI-980, ethyl [5-amino-1,2-dihydro-2(S)-methyl-3-[14C]phenylpyrido[3,4- 6]pyrazin-7-YL]carbamate isethionate salt, a tubulin-binding, antimitotic, broad-spectrum antitumor agent
✍ Peter W. K. Woo; Helen T. Lee 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 French ⚖ 408 KB

## Abstract [^14^C]CI‐980 (14b) was synthesized in eight steps starting from [U‐^14^C]benzene (5), which was converted to bromo[^14^C]benzene (6) in the presence of tetrabutylammonium bromide as catalyst. Reaction of 6 with the anion of __N__‐ethoxycarbonyl‐__N__′‐methoxy‐__N__′‐methyl‐L‐alaninamid