Diisopropylethylamine → HCID 24947293, compound

Participants

Reaction Steps

To a solution of 4-[bis(2-anilino-2-oxoethyl)amino]benzoic acid (40 mg, 0.099 mmol) in 2:1 CH2Cl2/DMF was added BOP (66 mg, 0.149 mmol), Hunigs base (26 μL, 0.149 mmol) and tert-butyl (3-aminobipheyl-4-yl)carbamate (56 mg, 0.199 mmol) and the reaction was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (20 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, MeOH-d4) δ 7.93 (d, J=8.9 Hz, 2H), 7.66 (dt, J=8.6, 1.5 Hz, 4H), 7.52 (d, J=7.2 Hz, 2H), 7.44 (s, 1H), 7.30 (m, 8H), 7.10 (t, J=7.8 Hz, 2H), 6.96 (d, J=7.8 Hz, 1H), 6.74 (d, J=9.1 Hz, 2H), 6.53 (t, J=7.2 Hz, 1H), 4.79 (s, 2H), 4.42 (s, 4H); MS: cal'd 570.2 (MH+), exp 570.2 (MH+).

Provenance & Evidence