2,4,6-Trichlorobenzoyl chloride → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium 7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (89.1 mg, 0.278 mmol) in NMP (6 mL) at 0° C. was added 2,4,6-trichlorobenzoyl chloride (43.5 μL, 0.278 mmol). The reaction mixture was stirred for 30 minutes. 1-((1,5-Dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine (50 mg, 0.186 mmol) was added and the mixture was heated at 87° C. for 3 hours. The reaction mixture was cooled to ambient temperature, and diluted with 10% NaOH aqueous solution (5 mL) and EtOAc (20 mL). The organic phase was washed with water and brine and then concentrated under reduced pressure. The residue was triturated with Et2O to give final product (71 mg). MS (ES+APCI) m/z=556 (M+H).

Provenance & Evidence