Water → Racemic-(trans)-2-[4-({[4-(2-pyridinyl)phenyl]methyl}amino)phenyl]cyclopropanecarboxamide

Participants

Reaction Steps

HATU (0.11 g, 0.29 mmol) and racemic-(trans)-2-[4-({[4-(2-pyridinyl)phenyl]methyl}amino)phenyl]cyclopropanecarboxylic acid (I-2c) (0.077 g, 0.22 mmol) in DMF (5 mL) were stirred at RT for 10 min, then ammonium hydroxide (2 mL) was added. The solution was stirred at RT for 16 h, then water (50 mL) and dichloromethane (50 mL) were added and the organic layer was separated, washed with water (50 mL), dried over Na2SO4, filtered and concentrated to give the title compound as a white powder (0.029 g, 38%). 1H NMR (400 MHz, DMSO) δ8.64 (d, J=3.8 Hz, 1H), 8.02 (d, J=8.1 Hz, 2H), 7.92 (d, J=8.0 Hz, 1H), 7.86 (t, J=7.9 Hz, 1H), 7.49 (s, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.33 (t, J=5.3 Hz, 1H), 6.81-6.79 (m, 3H), 6.50 (d, J=8.4 Hz, 2H), 6.19 (t, J=6.1 HZ, 1H), 4.30 (d, J=6.0 Hz, 2H), 2.05-2.00 (m, 1H), 1.64-1.60 (m, 1H), 1.20-1.15 (m, 1H), 1.03-0.98 (m, 1H). ES-MS m/z 344.2 (MH+).

Provenance & Evidence