Ammonium Chloride → 2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)-4-(pyrazolo[1,5-a]pyridin-3-ylmethylamino)pyridazin-3(2H)-one

Participants

Reaction Steps

To the solution of 3-(bromomethyl)pyrazolo[1,5-a]pyridine (3) (4 mL, 0.27 mmol, 0.0675 mmol/ml) in DCM (4 mL) was added TEA (33 mg, 0.33 mmol) and 4-amino-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyridazin-3(2H)-one (50 mg, 0.165 mmol) at room temperature and stirred for 1 h, then 10 mL sat. NH4Cl was added, extracted with EtOAc (3×10 mL). The combined organic phase were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by reverse phase chromatography (X bridge Prep C18OBD, 40-60% acetonitrile in water with 10 mmol NH4HCO3 modifier) to afford the compound as an oil. 1H NMR (400 MHz, MeOD) δ 8.47 (d, 1H), 8.03 (d, 1H), 7.96 (s, 1H), 7.67 (d, 1H), 7.26-7.11 (m, 3H), 6.87-6.84 (m, 1H), 5.85 (s, 1H), 4.50 (s, 2H), 4.17-4.13 (m, 1H), 4.02-3.97 (m, 1H), 3.82 (s, 3H), 3.59 (s, 3H), 2.06-2.02 (m, 1H), 1.75-1.71 (m, 1H), 1.17-1.13 (m, 1H) 1.02-0.99 (m, 1H); LRMS m/z (M+H) 433.1 found, 433.15 required.

Provenance & Evidence