4-Chloro-3-(trifluoromethyl)aniline → HCID 58674357, compound

Participants

Reaction Steps

A solution of 3-(4-{[2-(aminocarbonyl)pyridin-4-yl]oxy}phenyl)-propanoic acid (200 mg, 0.70 mmol), HATU (319 mg, 0.84 mmol), DIPEA (0.24 mL, 1.4 mmol), and 4-chloro-3-(trifluoromethyl)aniline (136 mg, 0.70 mmol) in DMF (5 mL) was stirred overnight at rt. EtOAc was added to the reaction and the mixture was washed with 1N HCl, 1N NaOH, and brine, dried over Na2SO4 and concentrated. Purification by column chromatography (SiO2, 20-100% EtOAc in hexane) followed by recrystallization in EtOAc/hexane provided A-3 (37 mg, 11%). 1H NMR (300 MHz, d6-DMSO) δ: 10.36 (s, 1H), 8.48 (d, J=5.7 Hz, 1H), 8.18 (d, J=2.5 Hz, 1H), 8.09 (bs, 1H), 7.81 (dd, J1=2.5 Hz, J2=8.8, 1H), 7.7 (bs, 1H), 7.64 (d, J=8.8 Hz, 1H), 7.35-7.40 (m, 3H), 7.12-7.16 (m, 3H), 2.97 (t, J=7.3 Hz, 2H), and 2.70 (t, J=7.8 Hz, 2H).

Provenance & Evidence