Methyl iodide → HCID 86696462, compound

Participants

Reaction Steps

To a solution of (S)-1-(2-(((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)methyl)pyrrolidin-1-yl)-3-methylbutan-1-one (380 mg, 1.0 mmol) in THF (10 mL) was added sodium hydride (120 mg, 3.0 mmol) at rt. After stirring for 15 min, methyl iodide was added dropwise. The reaction was stirred at it for overnight and worked up with ammonium chloride solution, extracted with ethyl acetate, concentrated and purified by ISCO column chromatography (10% MeOH/DCM) to give non-pure product. It was further purified by Prep HPLC (neutral) to give (S)-1-(2-(((3-bromoimidazo[1,2-b]pyridazin-6-yl)(methyl)amino)methyl)pyrrolidin-1-yl)-3-methylbutan-1-one as oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.65-7.75 (m, 1H), 7.44-7.52 (m, 1H), 7.04-7.22 (m, 1H), 4.45-4.61 (m, 1H), 3.45-3.92 (m, 4H), 3.19-3.23 (m, 3H), 1.90-2.32 (m, 7H), 0.78-0.92 (m, 6H); LRMS (ESI) m/e 394.1 [(M+H)+, calcd for C17H25BrN5O 395.3].

Provenance & Evidence