Potassium Phosphate, Tribasic → 3-(4-(aminomethyl)phenyl)-N-butylimidazo[1,2-b]pyridazin-6-amine mono acetic acid salt

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (190 mg, 0.71 mmol), (4-(aminomethyl)phenyl)boronic acid (331 mg, 1.76 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (26 mg, 0.036 mmol) and tripotassium phosphate (452 mg, 2.13 mmol) was added 1:1 dimethoxyethane/water (10 mL). The resulting mixture was heated at 160° C. (microwave) for 6 min. The reaction was then filtered and diluted with a mixture of 1:1:1 methanol/water/acetonitrile, and then filtered again. The filtration was finally purified by preparative HPLC (acidic) to afford 3-(4-(aminomethyl)phenyl)-N-butylimidazo[1,2-b]pyridazin-6-amine mono acetic acid salt (21 mg, 10% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.25-8.29 (m, 2H), 7.80 (s, 1H), 7.63 (d, J=9.6 Hz, 1H), 7.54 (d, J=8.3 Hz, 2H), 6.74 (s, 1H), 6.72 (s, 1H), 4.11 (s, 2H), 3.39 (t, J=7.1 Hz, 2H), 1.93 (s, 3H), 1.68-1.76 (m, 2H), 1.46-1.55 (m, 2H), 1.02 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 296.4 [(M+H)+, calcd for C17H22N5 296.2].

Provenance & Evidence