Tetrahydrofuran → HCID 178521456, compound

Participants

Reaction Steps

2-Chloro-1-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-ethanone (26 mg, 0.09 mmol, prepared in accordance with Example 4), trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanol (26 mg, 0.09 mmol, prepare in accordance with Example 5), and sodium hydride (10 mg, 60% in oil, 0.26 mmol) were placed under an inert atmosphere. Tetrahydrofuran (1 mL) was added under stirring. Next, dimethylformamide (300 μL) was added under stirring. The resulting mixture was stirred for 40 min at room temperature and then diluted with dichloromethane (5 mL). The mixture was washed with water (5 mL) and then washed with saturated aqueous sodium hydrogencarbonate (5 mL). The organic phase was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum. The crude product was purified by preparative HPLC. Following lyophilization of the fractions of interest, the desired product was isolated as a yellow solid (21 mg, 43% yield). The structure was confirmed using Protocol II-A. Calculated mass=575; observed mass=575; HPLC retention time=4.51 min.

Provenance & Evidence