Diisopropylethylamine → Methyl 4-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]phenyl}methyl)amino]carbonyl}benzoate

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Methyl 4-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]phenyl}methyl)amino]carbonyl}benzoate was prepared in a similar manner as described herein from 3-{[5-(aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile (0.05 g, 0.17 mmol), methyl 4-(chlorocarbonyl)benzoate (0.05 g, 0.25 mmol) and DIPEA (0.05 mL, 0.25 mmol). The crude material was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were lyophilized, neutralized and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.035 g, 45%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 9.22 (s, 1H), 7.98-8.06 (m, 2H), 7.92-7.98 (m, 2H), 7.80 (s, 1H), 7.60 (d, 1H), 7.45 (s, 1H), 7.38 (t, 1H), 7.25 (s, 1H), 7.23 (d, 1H), 4.47 (d, 2H), 3.86 (s, 3H). MS: m/z 455.0 (M+1).

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