1,2-Dichloroethane → HCID 66691716, compound

Participants

Reaction Steps

A mixture of 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylic acid (363 mg, 1.558 mmol, Preparation A), 4-chloro-2-nitro-5-(piperazin-1-yl)aniline (400 mg, 1.558 mmol, prepared as described in [El-Abadelah, M. M.; Nazer, M. Z.; El-Abadla, N. S.; Awadallah, A. M. Asian Journal of Chemistry 1999, 11(4), 1463-1468.]), EDC (448 mg, 2.337 mmol), and N,N-dimethylpyridin-4-amine (571 mg, 4.67 mmol) in DCM (5 mL)/DMF (3 mL) was stirred overnight. The solution was diluted with DCM, then washed with water for three times. Purification via flash chromatography with 20% EtOAc in DCM provided the title compound (286 mg, 0.606 mmol, 38.9% yield). 1H-NMR (CDCl3, 400 MHz): δ8.11 (1H, s), 7.59 (1H, d, J=7.53 Hz), 7.47 (1H, t, J=8.53 Hz), 7.08 (1H, t, J=7.53 Hz), 6.99 (1H, d, J=7.28 Hz), 6.03 (1H, s), 3.80 (3H, s), 3.8 (2H, s) 3.22 (2H, s), 3.01 (2H, s), 2.57 (3H, s), 2.46 (2H, s).

Provenance & Evidence