Phosphorus oxychloride → HCID 67976348, compound

Participants

Reaction Conditions

Reaction Steps

7-(2-(4-Methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (0.072 g, 0.21 mmol) was added to DMA (1 mL) and cooled to 0° C. Phosphorus oxychloride (0.038 mL, 0.41 mmol) was added and the reaction mixture was stirred for 30 minutes. 3-((4-Amino-1H-indazol-1-yl)methyl)-1-methylpyridin-2 (1H)-one (0.035 g, 0.14 mmol) was added and the reaction mixture was stirred at ambient temperature overnight. The reaction was concentrated and then suspended in 2 M LiOH (2 mL). The resulting mixture was stirred for 30 minutes and then diluted with CHCl3 and saturated aqueous NaHCO3. The layers were separated and the aqueous phase was extracted with CHCl3. The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by preparative thin layer chromatography (1:6 2.3 M NH3 in MeOH:CH2Cl2), added to MeOH (2 mL) and reacted with HCl (2 M in Et2O, 2 mL). The mixture was stirred for 60 minutes and then concentrated. The resulting solids were suspended in Et2O and filtered to provide N-(1-((1-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (0.035 g, 41% yield) as a solid. MS (ES+APCI) m/z=541 (M+H-2HCl).

Provenance & Evidence