Ammonium Chloride → HCID 59331648, compound

Participants

Reaction Steps

To a solution of (S)—N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-3-nitro-5-(trifluoromethyl)benzamide (74 mg, 0.16 mmol) in ethanol (3 mL) was added a solution of ammonium chloride (85 mg, 1.6 mmol) in water (1.5 mL), then indium powder (73 mg, mesh 100, 0.64 mmol). The mixture was heated at reflux for 40 hours, was allowed to cool to room temperature and was filtered through Celite. The filter cake was washed with ethanol and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL) and water (30 mL), the phases separated and the organic phase washed with brine (30 mL), dried (Na2SO4) and concentrated under reduced pressure to give a yellow oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give (S)-3-amino-N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-5-(trifluoromethyl)benzamide (45 mg, 65%) as a pale yellow solid.

Provenance & Evidence