Triethylamine → 1-(5-tert-Butyl-isoxazol-3-yl)-3-(4-{7-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-benzyl)-urea

Participants

Reaction Conditions

Reaction Steps

Combine {4-[3-(4-aminomethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone, bis hydrochloride (0.30 g, 0.56 mmol), (5-tert-butyl-isoxazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (0.2 g, 0.63 mmol) and triethylamine (0.4 mL, 2.9 mmol) in DMSO (10 mL). Heat the mixture to 70° C., stir five hours, and cool to room temperature. Filter the solution through 10 g SCX column eluting with methanol→2 N ammonia in methanol. Concentrate fractions containing product to give a residue. Purify by chromatography (5% methanol in dichloromethane→10% methanol in dichloromethane→10% 2 N ammonia methanol in dichloromethane) to afford product (0.048 g, 15%). MS(ES), m/z 592 (M+1).

Provenance & Evidence