Potassium Carbonate → HCID 57929852, compound

Participants

Reaction Conditions

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 (0.15 g, 0.35 mmol; Example #Q.1.2) was dissolved in DMF (4 mL) and then the K2CO3 (0.10 g, 0.71 mmol) and 1-bromo-2-methoxyethane (0.075 g, 0.53 mmol) were added. The mixture was heated at about 65° C. in an oil bath for about 1 h then another portion of 1-bromo-2-methoxyethane (0.075 g, 0.53 mmol) was added. After about 1 h, a third portion of 1-bromo-2-methoxyethane (0.075 g, 0.53 mmol) was added. The mixture was heated for about 1 h longer then cooled and concentrated under reduced pressure. The material was purified by RP-HPLC (Table 1, Method d). The appropriate fractions were concentrated and then basified with 2N NaOH and then extracted with EtOAc. Drying over MgSO4 and evaporating gave an oil which was purified further by flash chromatography on silica with DCM/MeOH (9:1) as an eluent. Concentration of the appropriate fractions followed by trituration with Et2O/heptane resulted in a solid which was collected by filtration to provide the title compound (0.086 g, 50%): LC/MS (Table 1, Method a) Rt=1.90 min; MS m/z: 482.2 (M+H)+.

Provenance & Evidence