BMS-794833

1174047-03-0

1174046-72-0

General procedure for the synthesis of N-(4-((2-amino-3-chloropyridin-4-yl)oxy)-3-fluorophenyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide from compound (CAS:1174047-03-0): at room temperature, N-(4-(3-chloro-2-(diphenylmethyleneamino)pyridin-4-yl oxy)-3-fluorophenyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide (410 mg, 0.65 mmol) solution in THF (10 mL) was slowly added to 2M HCl aqueous solution (0.81 mL, 1.62 mmol). The reaction mixture was stirred at room temperature for 1 hour and then concentrated under vacuum. The residue was cooled to room temperature and 5% aqueous cold hydrochloric acid solution (5 mL) was added. The precipitated solid was collected by filtration, washed sequentially with water and ether and finally dried under vacuum to give the target product (275 mg, 90% yield). The product was confirmed by 1H NMR (DMSO-d6) and mass spectrometry (ESI+): 1H NMR (DMSO-d6) δ 13.31 (s, 1H), 12.70 (br s, 1H), 8.63 (d, 1H, J = 1.30 Hz), 8.09 (d, 1H, J = 1.50 Hz), 8.02 (dd, 1H, J = 2.50, 13.10 Hz), 7.76 (d, 1H, J = 5.50 Hz), 7.71 (m, 2H), 7.44 (dd, 1H, J = 1.50, 8.80 Hz), 7.31 (t, 1H, J = 8.80 Hz), 7.27 (t, 2H, J = 8.80 Hz), 6.43 (br s, 2H), 5.96 (d, 1H, J = 5.60 Hz); MS (ESI+) m/z 469 (M + H)+.