Potassium Carbonate → 3-(6-(aminomethyl)pyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine acetic acid salt

Participants

Reaction Conditions

Reaction Steps

To a mixture of (6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)boronic acid (36 mg, 0.15 mmol), (5-bromopyridin-2-yl)methanamine (35 mg, 0.18 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5 mg, 0.01 mmol) and potassium carbonate (31 mg, 0.23 mmol) was added 3:1 acetonitrile/water (3 mL). The resulting mixture was heated at 145° C. (microwave) for 800 s. The reaction was then filtered and concentrated. The residue was dissolved in methanol, and then filtered again. The filtration was finally purified by preparative HPLC to afford 3-(6-(aminomethyl)pyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine acetic acid salt (13 mg, 29% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.64 (d, J=8.3 Hz, 1H), 7.91 (s, 1H), 7.66 (d, J=9.6 Hz, 1H), 6.77 (d, J=9.9 Hz, 1H), 3.39 (t, J=7.1 Hz, 2H), 1.94 (s, 4H), 1.71 (t, J=7.3 Hz, 2H), 1.41-1.58 (m, 2H), 1.01 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 297.4 [(M+H)+, calcd for C16H21N6, 297.2].

Provenance & Evidence