Acetyl chloride → N-butyl-3-(isoindolin-5-yl)imidazo[1,2-b]pyridazin-6-amine hydrochloride

Participants

Reaction Steps

The solution of tert-butyl 5-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)isoindoline-2-carboxylate (38 mg, 0.09 mmol) was cooled to 0° C. and treated with acetyl chloride (220 mg, 2.8 mmol). The reaction was maintained at room temperature for overnight. The resulting solution was concentrated under reduced pressure to afford N-butyl-3-(isoindolin-5-yl)imidazo[1,2-b]pyridazin-6-amine hydrochloride (12 mg, 35% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.26 (s, 1H), 8.17-8.21 (m, 2H), 7.98 (d, J=10.1 Hz, 1H), 7.65 (d, J=8.6 Hz, 1H), 7.27 (d, J=9.9 Hz, 1H), 4.76 (s, 4H), 3.36-3.45 (m, 2H), 1.63-1.81 (m, 2H), 1.40-1.56 (m, 2H), 1.00 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 308.4 [(M+H)+, calcd for C18H22N5 308.2].

Provenance & Evidence