1,3-Propanediamine → HCID 86696379, compound

Participants

Reaction Conditions

Reaction Steps

The solution of methyl aluminum (2.0 M in hexane, 0.32 mL, 0.64 mmol) in toluene (2 mL) was cooled to 0° C. Then to the stirring solution was respectively added dropwise propane-1,3-diamine (48 mg, 0.64 mmol), and the solution of methyl 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoate (130 mg, 0.4 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-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)imidazo[1,2-b]pyridazin-6-amine acetic acid salt (23.3 mg, 17% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.42-8.56 (m, J=8.6 Hz, 2H), 7.96 (s, 1H), 7.75-7.86 (m, J=8.6 Hz, 2H), 7.66 (d, J=9.6 Hz, 1H), 6.78 (d, J=9.9 Hz, 1H), 3.64 (t, J=5.8 Hz, 4H), 3.41 (t, J=7.1 Hz, 2H), 2.16 (t, J=5.7 Hz, 2H), 1.94 (s, 5H), 1.73 (t, J=7.2 Hz, 2H), 1.42-1.58 (m, 2H), 1.02 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 349.5 [(M+H)+, calcd for C20H24N6 349.2].

Provenance & Evidence