Patent ID: 9718779
Date: 2017-08-01
CPC Classifications: C07B,C07C,C07D

Claim:
1. A process for the preparation of 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl) phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide compound of formula-1, comprising: a) reacting 4-iodoaniline compound of formula-2 b) cyclizing the compound of formula-3 in presence of sodium tertiary butoxide in toluene to provide 1-(4-iodophenyl)piperidin-2-one compound of formula-4, c) reacting the compound of formula-4 with phosphorous pentachloride in dichloromethane to provide 3,3-dichloro-1-(4-iodophenyl)piperidin-2-one compound of formula-5, d) treating the compound of formula-5 with lithium carbonate and sodium chloride in dimethylformamide to provide 3-chloro-1-(4-iodophenyl)-5,6-dihydropyridin-2(1H)-one compound of formula-6, further purifying the obtained compound using methanol to provide pure compound of formula-6, e) reacting the compound of formula-6 with morpholine in toluene to provide 1-(4-iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one compound of formula-7, f) reacting the compound of formula-7 with piperidin-2-one in presence of copper iodide and potassium carbonate in o-xylene to provide 3-morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one compound of formula-8, g) condensing the compound of formula-8 with (Z)-ethyl 2-chloro-2-(2-(4-methoxyphenyl) hydrazono)acetate compound of formula-9 in presence of sodium carbonate in acetone to provide ethyl 1-(4-methoxyphenyl)-7a-morpholino-7-oxo-6-(4-(2-oxopiperidin-1-yl) phenyl)-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate compound of formula-10, h) treating the compound of formula-10 in-situ with dilute HCl to provide ethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate compound of formula-11, i) reacting the compound of formula-11 with formamide in presence of sodium methoxide in isopropanol to provide apixaban compound of formula-1, optionally purifying the compound with methanol to provide pure compound of formula-1, and j) purifying the compound of formula-1 using dichloromethane and methanol followed by isopropanol to provide pure apixaban compound of formula-1.