1,2-Dichloroethane → HCID 57857117, compound

Participants

Reaction Steps

To a solution of 4-[bis(2-anilino-2-oxoethyl)amino]benzoic acid (20 mg, 0.050 mmol) in DMF was added EDC (28 mg, 0.149 mmol), HOBt (20 mg, 0.149 mmol) and phenylenediamine (27 mg, 0.248 mmol) and the reaction was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (25 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and gave the desired N-(2-aminophenyl)-4-[bis(2-anilino-2-oxoethyl)amino]benzamide: 1H NMR (600 MHz, DMSO-d6) δ 10.90 (s, 2H), 9.31 (s, 1H), 7.83 (d, J=9.0 Hz, 2H), 7.64 (dd, J=8.6, 1.0 Hz, 4H), 7.33 (m, 4H), 7.07 (m, 3H), 6.89 (t, J=7.8 Hz, 1H), 6.70 (d, J=7.8 Hz, 1H), 6.60 (d, 9.1 Hz, 1H), 6.53 (t, J=7.2 Hz, 1H), 4.79 (s, 2H), 4.42 (s, 4H); MS: cal'd 494.2 (MH+), exp 494.2 (MH+).

Provenance & Evidence