Reaction Steps
A solution of 4-[({[3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoic acid (0.213 g, 0.5 mmol) and phenylenediamine (0.108 g, 1.0 mmol) in DMF (10 ml) was cooled to 0° C. Triethylamine (0.40 ml, 2.87 mol), 1-hydroxybenzotriazole (0.101 g, 0.75 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.144 g, 0.75 mmol) were added subsequently, and the mixture was stirred for 2 h at 0° C., and for an additional 96 h at room temperature. Ethyl acetate (40 ml) was added, and the obtained solution was washed with water (7 ml), Na2S2O3 1N (7 ml, aqueous solution), water (7 ml), NaHCO3 (7 ml, saturated aqueous solution), and NaCl (7 ml, saturated aqueous solution), dried over Na2SO4 and evaporated under reduced pressure, to obtain 0.142 g (0.27 mmol) of N-(4-{[(2-aminophenyl)amino]carbonyl}benzyl)-3-(4-methoxyphenyl)-5-Phenyl-1H-pyrrole-2-carboxamide: Yield 55%; m.p. 142-143° C. (dec); IR 3407, 3296, 1627, 1530, 1493, 1246 cm−1; 1H-NMR (300 MHz, δ ppm, DMSO-d6) 11.54 (s, 1H), 9.61 (s, 1H), 7.95 (d, J=7.8 Hz, 3H), 7.80 (d, J=7.4 Hz, 2H), 7.45-7.38 (m, 6H), 7.26 (t, J=7.3 Hz, 1H), 7.17 (d, J=7.7 Hz, 1H), 6.97 (dt, J=8.0 Hz, J′=1.4 Hz, 1H), 6.90 (d, J=8.7 Hz, 2H), 6.79 (dd, J=7.9 Hz, J′=1.1 Hz, 1H), 6.67 (d, J=2.6 Hz, 1H), 6.60 (dt, J=7.5 Hz, J′=1.0 Hz, 1H), 4.86 (s, 2H), 4.49 (d, J=5.7 Hz, 2H), 3.77 (s, 3H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 165.0, 161.1, 157.9, 143.0, 142.9, 133.1, 132.9, 131.5, 129.9, 128.6, 127.9, 127.8, 127.7, 127.1, 126.7, 126.6, 126.4, 124.5, 123.3, 122.6, 116.2, 116.1, 113.4, 108.3, 55.0, 42.1.
