Triethylamine → 1-((1R,2S)-2-(((3-(4-fluorophenyl)propyl)(methyl)amino)methyl)cyclohexyl)-3-(3-(1-methyl-1H-tetrazol-5-yl)phenyl)urea

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Reaction Steps

A solution of (1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine (72 mg, 259 μmol) in acetonitrile (2 mL) was treated with triethylamine (72 μL, 517 μmol) and [3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (76 mg, 259 μmol). The mixture was stirred at room temperature for 15.5 hours and then was concentrated under vacuum. The residue was dissolved in ethyl acetate, and the solution was washed sequentially with 1.0 M aqueous sodium hydroxide, water and saturated aqueous sodium chloride. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 4% methanol in dichloromethane containing 0.4% aqueous ammonium hydroxide, to provide a white amorphous solid (75 mg, 60%).

Provenance & Evidence