Triethylamine → N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]pyridine-3-carboxamide

Participants

Reaction Steps

To a solution of 5-aminomethyl-4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (245 mg, 0.97 mmole) and triethylamine (202 mg, 2 mmole) in 10 mL of anhydrous DMF was added nicotinoyl chloride (178 mg, 1.0 mmol) in 7 mL of anhydrous DMF. The reaction was stirred at ambient temperature for 1 hour, and then mixed with saline and ethyl acetate. The title compound was purified by column chromatography (CH2Cl2:CH3OH=13:1) to yield 119 mg of the title compound as a yellow powder. MS (m/z, ES−): 356 (M−1, 20%); 1H NMR (ppm, 400 MHz, DMSO-d6) □δ 11.86 (br s, 1H), 9.04 (brs, 1H), 9.01 (s, 1H), 8.67 (d, 1H), 8.19 (d, 1H), 7.71 (dd, 1H), 7.57 (m, 1H), 7.47 (m, 2H), 7.11 (br s, 2H), 4.69 (s, 2H).

Provenance & Evidence