Water → HCID 86696370, compound

Participants

Reaction Conditions

Reaction Steps

The solution of methyl aluminum (2.0 M in hexane, 0.31 mL, 0.62 mmol) in toluene (2 mL) was cooled to 0° C. Then to the stirring solution was respectively added dropwise ethane-1,2-diamine (37.4 mg, 0.62 mmol), and the solution of methyl 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoate (126 mg, 0.39 mmol) in toluene (1 mL). The resulting reaction was refluxed at 110° C. overnight, and then cooled to 0° C. To the solution was added dropwise water (0.05 mL), methanol (0.2 mL) and chloroform (0.2 mL). The resulting mixture was refluxed on a steam bath for 15 m, and then filtered over sodium sulfate and concentrated. The residue was purified by preparative HPLC to afford N-butyl-3-(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)imidazo[1,2-b]pyridazin-6-amine acetic acid salt (3.9 mg, 3% yield) as a yellow solid: 1H NMR (METHANOL-d4) δ: 8.46-8.59 (m, J=8.8 Hz, 2H), 8.01 (s, 1H), 7.93-7.98 (m, J=8.8 Hz, 2H), 7.67 (d, J=9.9 Hz, 1H), 6.80 (d, J=9.6 Hz, 1H), 4.13 (s, 4H), 3.42 (t, J=7.1 Hz, 2H), 1.86-2.05 (m, 6H), 1.74 (t, J=7.2 Hz, 2H), 1.39-1.61 (m, 2H), 1.03 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 335.4 [(M+H)+, calcd for C19H23N6 335.2].

Provenance & Evidence