Patent ID: 7384939

Claim:
A process for producing a carboxamide pyridine compound of the formula: said method comprising: (a) reacting a pyridinium salt of the formula: with an α-cyano-β-aryl acrylate compound of the formula: to produce a pyridinium zwitter ionic compound of the formula: (b) reacting the pyridinium zwitter ionic compound with a reagent selected from the group consisting of POCl 3 , PBr 3 , and (F 3 CSO 2 ) 2 O, to form a cyanopyridine compound of formula: (c) reacting the cyanopyridine compound of formula VIII with an amine compound of the formula HNR 2 R 3 to form a tetra-substituted pyridine compound of the formula: (d) hydrogenating the tetra-substituted pyridine compound formula IX in the presence of a hydrogenation catalyst to form a tri-substituted pyridine compound of the formula: and (e) hydrolyzing the tri-substituted pyridine compound to form the carboxamide compound of Formula I, wherein each R 1 is independently lower alkyl, lower alkoxy, halogen, cyano or alkylamino; a is an integer from 0 to 2; R 2 is hydrogen, C 3-6 cycloalkyl, aralkyl, lower alkyl, hydroxylalkyl, —S(O) 2 -lower alkyl, —S(O) 2 —Ar 1 , (optionally substituted N-heterocyclyl)alkyl, —C(═O)R 3 , where Ar 1 is aryl; R 3 is hydrogen, C 3-6 cycloalkyl, aralkyl or lower alkyl; or R 2 and R 3 together with the nitrogen atom to which they are attached to form optionally substituted N-heterocyclyl; or R 2 and R 3 together form ═C(R 5 )—R 6 —NR 7 R 8 ; where R 5 is lower alkyl, or hydrogen; R 6 is alkylene, or a bond; and each of R 7 and R 8 is independently hydrogen, C 3-6 cycloalkyl, aralkyl, or lower alkyl; R 9 is lower alkyl; X 1 is halide or trifluoromethanesufonate; and X is halide.