Triethylamine → HCID 67260151, compound

Participants

Reaction Steps

N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(3-hydroxypropyl)imidazo[1,2-a]pyridine-3-carboxamide (77 mg, 0.16 mmol) was dissolved in tetrahydrofuran (0.8 mL) and treated with triethylamine (66 μL, 0.48 mmol) followed by dropwise addition of methanesulfonyl chloride (38 mL, 0.49 mmol). The mixture was stirred at ambient temperature for 2.5 hours. 1-Methyl piperazine (365 μL, 3.3 mmol) was added and the mixture was heated to 60° C. for 10 hours. The mixture was quenched with the addition of saturated sodium bicarbonate solution and extracted with dichloromethane 3 times. The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography (silica, 2 mm) eluting with 10% methanol/dichloromethane with 0.2% ammonium hydroxide to give N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(3-(4-methylpiperazin-1-yl)propyl) imidazo[1,2-a]pyridine-3-carboxamide (10 mg). MS m/z 551.4 (M+1, APCI+).

Provenance & Evidence