Dichloromethane → N-(3-ethyl-1-((6-(piperazin-1-yl)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide trihydrochloride

Participants

Reaction Steps

To a solution of tert-butyl 4-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl)piperazine-1-carboxylate (12 mg, 0.021 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1 mL). The mixture was stirred for 1 hour at ambient temperature. The solution was concentrated under reduced pressure. The residue was re-dissolved in a mixture of dichloromethane and methanol and neutralized by the addition of ammonium hydroxide solution. The solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica, eluting with 15% methanol in dichloromethane containing 1% ammonium hydroxide solution. The isolated product was dissolved in a mixture of ethyl acetate, methanol and dichloromethane. Concentrated hydrochloric acid (2 drops) was added. Concentration under reduced pressure followed by high vacuum gave N-(3-ethyl-1-((6-(piperazin-1-yl)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide trihydrochloride (5.0 mg). MS (APCI), positive scan, m/z=481.3 (M+H).

Provenance & Evidence