Dimethyl Sulfoxide → (S)-1-(2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)-2-(1H-1,2,4-triazol-5-yl)ethanone

Participants

Reaction Steps

A solution of (S)-5-(3-benzylpiperazin-1-yl)-8-methoxy-2-(trifluoromethyl)quinoline (Example 65, Compound 153) (100.0 mg, 0.25 mmol), (4H-[1,2,4]triazol-3-yl)-acetic acid ethyl ester (83 mg, 0.50 mmol), sodium cyanide (24 mg, 0.50 mmol), and DMSO (2 mL). The reaction mixture was heated in a heat block at 100 C for 24 h then cooled to room temperature, diluted with EtOAc, and washed with water followed by brine. The organic portion was dried over MgSO4, filtered, evaporated and purified by silica gel flash chromatography to afford product as a colorless solid (0.9 mg, 0.7%). LC/MS (Method B) 3.32 min, [m/z=510.9].

Provenance & Evidence