3-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine → HCID 136378623, compound

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Reaction Steps

Following the Suzuki coupling conditions described in example 5.6.45 from (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine (213.1 mg, 0.8 mmol), and 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one (308.2 mg, 1.1 mmol) to provide 70.9 mg of 3-[4-(6-butylamino-imidazo[1,2-b]pyridazin-3-yl)-phenyl]-4H-[1,2,4]oxadiazol-5-one as white crystalline powder, mp. 253-254° C. (dec.). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (t, J=7.33 Hz, 3H) 1.44 (sxt, J=7.38 Hz, 2H) 1.65 (quin, J=7.26 Hz, 2H) 3.26-3.35 (m, 2H) 6.75 (d, J=9.85 Hz, 1H) 7.15 (t, J=5.31 Hz, 1H) 7.77 (d, J=9.60 Hz, 1H) 7.88 (m, J=8.84 Hz, 2H) 8.05 (s, 1H) 8.44 (m, J=8.59 Hz, 2H). 13C NMR (100 MHz, DMSO-d6) δ ppm 13.73, 19.89, 30.15, 40.81, 112.82, 120.91, 125.38, 125.50, 126.11, 131.05, 133.01, 137.80, 153.62, 157.06, 159.94. LRMS (ESI) m/z 351.2 [(M+H)]+, calc'd for C18H18N6O2: 350.38.

Provenance & Evidence