FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing a compound of formula: , where R1 is an optionally substituted phenyl; L is a binding group of formula: -(CR7a R7b)n-, where R7a and R7b are hydrogen; R8 is hydrogen; and index n equals 1; or a pharmaceutically acceptable salt thereof, involving: A) reaction of boric acid or ester thereof of formula: , where Y is OR20, R20 is hydrogen, with 3,5-dihalo-2-cyanopyridine presented by formula: , each Z independently represents chlorine or bromine, in presence of a catalyst to form optionally substituted in position 5 phenyl-3-halo-2-cyanopyridine of formula: ; B) reaction of optionally substituted in position 5 phenyl-3-halo-2-cyanopyridine obtained at step (A), with an alkoxide anion of formula: , where R2 is C1-C-6alkyl, to form a 5 optionally substituted in position 5 phenyl-3-alkoxy-2-cyanopyridine, presented by formula: ; C) reaction of optionally substituted in position 5 phenyl-3-alkoxy-2-cyanopyridine, obtained at step (B), with an acid to produce optionally substituted in position 5 phenyl-3-hydroxy-2-carboxypyridine of formula: ; D) reacting optionally substituted in position 5 phenyl-3-hydroxy-2-carboxypyridine, obtained at step (C), with an amino acid, represented by formula: where X is -OR3; R3 is C1-C6alkyl; and e) hydrolysis of compound obtained at step D). Invention also relates to a method of producing a compound of formula: .
EFFECT: technical result is obtaining [(3-hydroxypyridine-2-carbonyl)amino]alkanoic acids, esters and amides thereof using a novel simplified method.
12 cl, 3 dwg, 5 ex
Authors
Dates
2016-11-10—Published
2012-06-05—Filed