Dichloromethane → N-(3-ethyl-1-((1-(2-(piperazin-1-yl)ethyl)-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide trihydrochloride

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-(3-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)-1H-pyrazol-1-yl)ethyl)piperazine-1-carboxylate (21.5 mg; 0.0360 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (1 mL). The mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was dissolved in a mixture of methanol and dichloromethane. Ammonium hydroxide solution was added to neutralize. The material was purified by preparative thin layer chromatography on silica, eluting with 15% methanol in dichloromethane containing 0.5% ammonium hydroxide solution. The isolated product was dissolved in a mixture of methanol and ethyl acetate and treated with hydrogen chloride (1 mL; 2M in ether). Removal of solvent under reduced pressure followed by high vacuum gave N-(3-ethyl-1-((1-(2-(piperazin-1-yl)ethyl)-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide trihydrochloride (9.5 mg). MS (APCI), positive scan, m/z=498.3 (M+H).

Provenance & Evidence