Acetonitrile → (2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine (150 mg, 0.28 mmol) and NaOAc.3H2O (77.6 mg, 0.57 mmol) in methanol was added cyanogen bromide in acetonitrile (5.0 M, 0.1 mL, 0.5 mmol). The slurry was stirred at room temperature overnight. The mixture was loaded onto a samplet and purified by chromatography over 25+S Biotage silica column (eluted with 0-30% ethyl acetate in heptane) to afford the title compound (144.1 mg, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-1.19 (m, 6H) 1.41-1.53 (m, 1H) 1.62 (d, J=7.88 Hz, 2H) 1.71-1.79 (m, 1H) 1.96 (d, J=12.45 Hz, 1H) 3.16 (s, 3H) 4.00 (d, J=7.47 Hz, 1H) 4.32 (d, J=14.11 Hz, 1H) 4.32 (s, 2H) 4.40 (d, J=14.11 Hz, 1H) 7.50 (d, J=8.30 Hz, 1H) 7.54 (s, 1H) 7.63 (d, J=8.30 Hz, 1H) 7.78 (s, 2H) 7.91 (s, 1H). MS (ES−) Calc: 552.2, Found: 551.5 (M−1).

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