N-methyl-2-pyrrolidone → HCID 67976263, compound

Participants

Reaction Steps

A vial containing lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (0.171 g, 0.550 mmol) and NMP (3.0 mL) was warmed to provide a homogeneous solution and then cooled to ambient temperature. 2,4,6-Trichlorobenzoyl chloride (0.0803 mL, 0.513 mmol) was added and the dark solution was stirred at ambient temperature for 0.5 hours. 7-Chloro-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (0.100 g, 0.367 mmol) was added as a NMP (3.0 mL) solution and the mixture was heated to 80° C. with stirring overnight. The reaction was equilibrated to ambient temperature and the mixture was diluted with EtOAc (30 mL) and saturated aqueous NaHCO3 (10 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (15% IPA/CHCl3 adding 1% 7N NH3/MeOH) to provide N-(7-chloro-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide. This product was dissolved in MeOH (4.0 mL) and CH2Cl2 (1.0 mL), and HCl (3.67 mL, 7.33 mmol, 2.0M Et2O) was added. The mixture was stirred for 2 hours and then concentrated. The resulting solid was then washed with Et2O and finally with hexanes and dried under vacuum overnight to provide 0.140 g (50%) of the title compound. MS (ES+APCI) m/z=559 (M+H-3HCl).

Provenance & Evidence