4-Chloroaniline → HCID 58674407, compound

Participants

Reaction Steps

A solution of 3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanoic acid (400 mg, 1.49 mmol), HATU (681 mg, 1.79 mmol), DIPEA (0.5 mL, 2.98 mmol), and 4-chloroaniline (209 mg, 1.63 mmol) in DMF (5 mL) was stirred overnight at rt. The reaction mixture was diluted with EtOAc and washed with 1N HCl, 1N NaOH and brine, dried over Na2SO4 and concentrated. The resulting solid was triturated with DCM and filtered to give A-21 (187 mg, 33%). 1H NMR (300 MHz, d6-DMSO): δ 10.02 (s, 1H), 8.56 (dd, J1=0.50 Hz, J2=5.8 Hz, 1H), 7.57-7.63 (m, 3H), 7.31-7.40 (m, 4H), 7.10-7.17 (m, 3H), 2.95 (t, J=7.5 Hz, 2H), and 2.65 (t, J=7.8 Hz, 2H).

Provenance & Evidence