Sodium Sulfate → HCID 86724970, compound

Participants

Reaction Steps

Under a nitrogen gas atmosphere, anhydrous sodium sulfate (1.4 g) was added at room temperature to a solution of (7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde (synthesized with reference to WO2009/1126; 167 mg, 0.765 mmol) and 6-[(4R)-4-(aminomethyl)-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (200 mg, 0.765 mmol) in dichloromethane (3 ml)/N,N-dimethylformamide (1 ml) and the mixture was stirred at the same temperature for 2 hours. Dichloromethane (3 ml) was added to the reaction solution, sodium triacetoxyborohydride (243 mg, 1.15 mmol) was subsequently added thereto and the mixture was stirred at the same temperature for 15 hours. Water (10 ml) was added to the reaction solution to dissolve the insoluble material and then a mixture of dichloromethane and a saturated sodium hydrogen carbonate aqueous solution was poured thereinto and the resultant was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol) to yield 321 mg (90%) of the title compound in the form of a light yellow amorphous solid.

Provenance & Evidence