Dimethylformamide → HCID 89761899, compound

Participants

Reaction Steps

A vial was charged with 1-(2-chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide (INTERMEDIATE V, 0.045 g, 0.072 mmol) and DMF (0.719 mL). Sodium hydride (60% in mineral oil) (4.31 mg, 0.108 mmol) was added to give a dark brown solution. Acetic anhydride (0.014 mL, 0.144 mmol) was added dropwise, and the mixture lightened significantly and thickened up. After stirring for 30 minutes at room temperature, additional acetic anhydride (0.014 mL, 0.144 mmol) was added and the reaction was heated to 50° C. and stirred for one hour. Additional sodium hydride (60% in mineral oil) (4.31 mg, 0.108 mmol) and acetic anhydride (0.014 mL, 0.144 mmol) were added and the reaction was stirred at 70° C. for one hour. The mixture was diluted with water and EtOAc, then with brine to break up an emulsion. The layers were separated, and the aqueous layer was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, and concentrated. The material was purified via silica gel chromatography (12 g column, gradient elution 0 to 100% EtOAc:Heptane) to afford 4-acetyl-1-(2-chloro-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)-1,2,3,4-tetrahydroquinoxaline-6-sulfonamide as a white solid. m/z (ESI) 667.7 (M+H)+.

Provenance & Evidence