O-Phenylenediamine → N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-1H-benzo[d]imidazol-2-amine

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반응 단계

5-chloro-2-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-isothiocyanato-2-phenylethyl)pyridine (0.036 g, 0.083 mmol) in dichloroethane (1 mL) in a two drum vial was added phenylenediamine (12 mg, 0.108 mmol) and TEA (13 mL, 0.091 mmol). The reaction was heated at 80° C. for 2 hours. EDCI (24 mg, 0.124 mmol) was added and the reaction was continued to be heated at 80° C. overnight. The reaction was concentrated and the crude mixture was purified by ISCO chromatography (12 g column) using hexanes/EtOAc (0-40% over 25 min) to give N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-1H-benzo[d]imidazol-2-amine as a white solid (20 mg, 47% yield). LCMS: 3.2 min [M+1] 511.22 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CD3OD) d ppm 4.01-4.10 (m, 1H), 4.51 (d, J=13.21 Hz, 1H), 6.48 (d, J=7.34 Hz, 2H), 6.93-7.04 (m, 5H), 7.22 (dd, J=5.50, 3.06 Hz, 2H), 7.34 (d, J=8.31 Hz, 1H), 7.51-7.58 (m, 1H), 7.71-7.77 (m, 2H), 7.82 (dd, J=8.56, 2.45 Hz, 1H), 8.41 (d, J=2.45 Hz, 1H).

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