Formaldehyde → HCID 57929979, compound

Participants

Reaction Steps

The 6-(3-(2,4-difluorophenyl)-1-(piperidin-4-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine (0.10 g, 0.24 mmol; Example #Q.2.1) was suspended in DCE (5 mL) and then formaldehyde (30% solution in water, 0.12 g, 1.18 mmol) and sodium triacetoxyborohydride (0.10 g, 0.47 mmol) were added. After about 1 h, the mixture was concentrated under reduced pressure, dissolved in DMF/HOAc, and purified by RP-HPLC (Table 1, Method d). The appropriate fractions were combined and concentrated under reduced pressure and then the mixture was basified with 2 N NaOH and extracted with EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated under reduced pressure. Evaporation several times with Et2O/heptane gave a white solid which was collected by filtration and dried under vacuum to give the title compound (0.042 g, 41%): LC/MS (Table 1, Method a) Rt=1.83 min; MS m/z: 438.2 (M+H)+.

Provenance & Evidence