2-Amino-4-phenylphenol → 2-(4-{[(4-hydroxybiphenyl-3-yl)amino]carbonyl}phenyl)-N,N'-diphenylmalonamide

Participants

Reaction Steps

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (33 mg, 0.088 mmol) in DMF (1 mL) at room temperature was added EDCI (13 mg, 0.094 mmol) and HOBT (19 mg, 0.14 mmol). The solution was stirred for 30 min and 2-amino-4-phenylphenol (33 mg, 0.18 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h and purified directly by reverse phase HPLC (40% to 95% MeCN in water) to give 2-(4-{[(4-hydroxybiphenyl-3-yl)amino]carbonyl}phenyl)-N,N′-diphenylmalonamide (27 mg, 57%) as a white solid: 1H NMR (600 MHz, DMSO-d6) δ 10.27 (s br, 2H), 9.96 (s br, 1H), 9:58 (s br, 1H), 8.01-7.97 (m, 3H), 7.59-7.55 (m, 8H), 7.41 (t, J=7.9 Hz, 2H), 7.35-7.27 (m, 6H), 7.04 (t, J=7.0 Hz, 2H), 6.98 (d, J=8.2 Hz, 1H), 4.97 (s, 1H); ESIMS calcd 542.2 (M++H), found 542.1 (M++H).

Provenance & Evidence