Triethylamine → N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-N'-((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)urea

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A mixture of N-(2RS)-{[(1S,2R)-2-aminocyclohexyl]methyl}-6-fluoro-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine (60 mg, 206 μmol), phenyl[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]carbamate (52 mg, 206 μmol), triethylamine (57 μL, 412 μmol) and acetonitrile (2 mL) was stirred at room temperature for 16 hours. The mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with aqueous sodium hydroxide (1.0 N), dried over sodium sulfate, and concentrated. The residue was purified by flash column chromatography, eluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonia, to provide an amorphous solid (40 mg, 37%) which was a mixture of two diastereomers by NMR.

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