O-Phenylenediamine → HCID 11988294, compound

Participants

Reaction Steps

To a solution of 4-(2-[(3-chlorophenyl)amino]-1-{[(3-chlorophenyl)amino]carbonyl}-2-oxoethyl)benzoic acid (61 mg, 0.14 mmol) in DMF (3 mL) at room temperature was added EDCI (31 mg, 0.16 mmol) and HOBT (22 mg, 0.16 mmol). The solution was stirred for 30 min and 1,2-phenylenediamine (45 mg, 0.42 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h and purified directly by reverse phase HPLC (20% to 80% MeCN in water) to give 2-(4-{[(2-aminophenyl)amino]carbonyl}phenyl)-N,N′-bis(3-chlorophenyl)malonamide (46 mg, TFA salt, 52%) as a white solid: 1H NMR (600 MHz, CD3OD) δ 8.06 (d, J=8.2 Hz, 2H), 7.79 (t, J=2.1 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.44 (dd, J=8.2, 1.2 Hz, 2H), 7.36 (d, J=7.9 Hz, 1H), 7.33-7.24 (m, 5H), 7.11 (dd, J=7.9, 0.8 Hz, 2H); ESIMS calcd 533.1 (M++H), found 533.0 (M++H).

Provenance & Evidence