1,2-Dichloroethane → 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carbonyl)-N-phenylhydrazinecarboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carboxylic acid (204.5 mg, 0.732 mmol), 4-phenylsemicarbazide (111 mg, 0.732 mmol), EDC (140 mg, 0.732 mmol), and HOBT (112 mg, 0.732 mmol) in DMF (3.5 mL) was stirred at 25° C. for 3 h. DIPEA (0.255 mL, 1.464 mmol) was added and the resulting mixture was stirred at 25° C. for 2 h. Additional 4-phenylsemicarbazide (111 mg, 0.732 mmol), HOBT (112 mg, 0.732 mmol), and EDC (140 mg, 0.732 mmol) were sequentially added, and the resulting mixture was stirred at 25° C. for 17 h. The mixture was diluted with H2O (40 mL), and the precipitated solid was collected by vacuum filtration, sequentially washed with H2O (2×30 mL) and Et2O (2×15 mL), and dried in vacuo to provide 2-(3-(6-cyclopropylpyrazin-2-yl)-1H-indole-5-carbonyl)-N-phenylhydrazinecarboxamide (262 mg, 0.635 mmol, 87%) as a tan solid: MS (ESI, pos. ion) m/z: 413.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.90-11.97 (1H, m), 10.19-10.25 (1H, m), 8.97-9.00 (1H, m), 8.94-8.97 (1H, m), 8.84 (1H, s), 8.36 (1H, s), 8.32 (1H, d, J=2.7 Hz), 8.15 (1H, s), 7.79 (1H, d, J=8.4 Hz), 7.51-7.55 (1H, m), 7.50 (2H, d, J=8.0 Hz), 7.27 (2H, t, J=7.7 Hz), 6.96 (1H, t, J=7.3 Hz), 2.18-2.27 (1H, m), 1.16-1.22 (2H, m), 1.04-1.13 (2H, m).

Provenance & Evidence