Hydrochloric Acid → HCID 178433614, compound

Participants

Reaction Steps

To a solution of 3-[methyl(propan-2-yl)amino]-2-[2-methyl-3-(2,2,2-trifluoroacetyl)-1H-indol-5-yl]quinoxaline-6-carbonitrile (160 mg, 0.35 mmol) in DMSO (20 ml) was added ZnBr2 (38 mg, 0.17 mmol) and NaN3 (91 mg, 1.40 mmol) in water (2 ml). The resulting solution was heated to reflux overnight and diluted with water (200 ml), adjusted to pH 3 with HCl (2N), extracted with ethyl acetate (5×50 ml), and the organic layers combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (15% dichloromethane in methanol) to afford 2,2,2-trifluoro-1-(5-(3-(isopropyl(methyl)amino)-6-(1H-tetrazol-5-yl)quinoxalin-2-yl)-2-methyl-1H-indol-3-yl)ethanone as a yellow solid (38.6 mg, 27%).

Provenance & Evidence