Cyclohexylamine → (3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydropyran-4-yl)-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-6-fluoroimidazo[1,2-b]pyridazine (1.1 g, 5.0 mmol), cyclohexylamine (0.86 mL, 7.5 mmol), cesium carbonate (3.3 g, 10 mmol), and DMF (10 mL) was maintained at 40° C. for 6 h, then cooled to RT and partitioned between ethyl acetate (100 mL) and H2O (100 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (4×40 mL). The combined organic layers were washed with H2O (100 mL) and brine (100 mL), then dried (MgSO4), filtered and concentrated to afford a residue that was purified by flash chromatography (SiO2) to afford 3-bromo-N-(tetrahydro-pyran-4-yl)imidazo[1,2-b]pyridazin-6-amine (1.1 g, 73%) as a light yellow solid: 1H NMR (400 MHz, MeOD) δ 7.53 (d, J=9.6 Hz, 1H), 7.39 (s, 1H), 6.68 (d, J=9.9 Hz, 1H), 3.68-3.87 (m, 1H), 2.14 (dd, J=12.6, 3.3 Hz, 2H), 1.82 (dt, J=13.3, 3.7 Hz, 2H), 1.70 (dt, J=12.8, 3.7 Hz, 1H), 1.38-1.52 (m, 2H), 1.23-1.38 (m, 3H); LCMS (ESI) m/e 295.2 [(M+H)+, calcd for C12H15BrN4 295.1].

Provenance & Evidence