22934-23-2Relevant articles and documents
Innovative approaches to the imidazo[4,5-b]pyridine ring system. Development of an efficient process for industrial-scale production of a key intermediate for potent angiotensin II receptor antagonists
Stucky, Gerhard C.,Roduit, Jean-Paul,Schmidt, Beat
, p. 280 - 282 (2007/10/03)
Two syntheses of 2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (3), an important intermediate for the synthesis of several potent angiotensin II antagonists, have been investigated. The first route involves conversion of 1,1-bis(methylthio)-2-nitroethene (17) to 2-ammo-4,6-dimethyl-3-nitropyridine (6); catalytic hydrogenation of 6 in propionic acid gave 3 in high yield. In the second synthesis, propionitrile is converted to imidate hydrochloride 15·HCl which is neutralised and reacted with aminoacetonitrile in the presence of acetylacetone to give 3 in 55% overall yield. The propionitrile route was scaled up to produce 3 in the pilot plant.
Polyfunctional pyridines from nitroacetamidine and β-diketones. A useful synthesis of substituted imidazo[4,5-b]pyridines and related compounds
Batt,Houghton
, p. 963 - 969 (2007/10/02)
Nitroacetamidine undergoes a useful cyclocondensation with β-diketones to produce substituted 2-amino-3-nitropyridines. Use of an acylpyruvate generates hitherto unreported 2-amino-3-nitropyridine-4-carboxylates. These may be converted easily to functionalized imidazo[4,5-b]pyridines and oxazolo[5,4-b]pyridines.
Angiotensin II antagonists incorporating a substituted thiophene or furan
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, (2008/06/13)
There are disclosed substituted thiophene and furan derivatives of Formula I which are useful as angiotensin II antagonists. STR1