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Synthesis of 6‐[[(hydroxyimino)phenyl]methyl]‐1‐[(1‐methylethyl)sulfonyl]‐1 H ‐imidazo[4,5‐ b ]pyridin‐2‐amine. An aza analogue of enviroxime
Author(s) -
Kelley James L.,
Mclean Ed W.,
Davis Ronda G.,
Crouch Ronald
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270656
Subject(s) - chemistry , moiety , sulfonyl , hydroxylamine , amine gas treating , ketone , medicinal chemistry , phosphorus pentachloride , nitro , pyridine , stereochemistry , organic chemistry , alkyl
6‐[[(Hydroxyimino)phenyl]methyl]‐1‐[(1‐methylethyl)sulfonyl]‐1 H ‐imidazo[4,5‐ b ]pyridin‐2‐amine ( 1 ), an aza analogue of enviroxime, was synthesized in eight steps from 6‐hydroxynicotinic acid ( 2 ). Acid 2 was nitrated, chlorinated with phosphorus pentachloride, and subjected to Friedel‐Crafts aroylation to give 6‐chloro‐5‐nitro‐3‐pyridyl phenyl ketone ( 5 ). Amination of 5 was followed by reduction of the nitro group and condensation with ethoxycarbonylisothiocyanate to give 6‐benzyl‐2‐ethoxycarbonylamino‐1 H ‐imidazo[4,5‐ d ]pyridine ( 8 ). The ethoxycarbonyl moiety of 8 was cleaved, N‐1 was isopropylsulfonylated, and the carbonyl moiety was condensed with hydroxylamine to give 1 . Compound 1 was inactive against rhinovirus 1B and poliovirus type 1 .