Nitrogen → 1-(4-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)piperazin-1-yl)-3,3-dimethylbutan-1-one

Participants

Reaction Steps

To a rapidly stirred, ambient temperature, N2 blanketed, suspension of 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine (dihydrochloride (400.5 mg, 1.1 mmol) and 3,3-dimethylbutanoyl chloride [7065-46-5] (0.2 mL, 1.4 mmol) in ethyl acetate (50 mL) was added Hunig's base [7087-68-5] (0.8 mL, 4.6 mmol) and the reaction allowed to stir over night. Once complete, the reaction was washed with brine, dried (MgSO4), and crystallized from chilled ethyl acetate/heptane to afford 392.5 mg of white crystalline powder, mp. 170-171° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02 (s, 9H) 2.30 (s, 2H) 3.57 (d, J=7.06 Hz, 4H) 3.63-3.72 (m, 4H) 7.26 (d, J=9.92 Hz, 1H) 7.63 (s, 1H) 7.91 (d, J=9.92 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm 29.57, 30.81, 40.12, 43.50, 45.26, 45.34, 99.17, 110.56, 125.96, 131.44, 136.42, 154.89, 169.49. LRMS (ESI) m/z 380.1/382.1 [(M+H)]+, calc'd for C16H22BrN5O: 380.28.

Provenance & Evidence