Acetic Acid → 5-Amino-1-(3-carboxyphenyl)-3-(4-tolyl)pyrazole-4-carboxamide

Participants

Reaction Steps

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acrylamide (464 mg, 2.0 mmol), 3-carboxyphenylhydrazine (304 mg, 2.0 mmol) and triethylamine (2 ml) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 2% acetic acid, 5% methanol in CH2Cl2) to give the title compound as a light yellow solid (340 mg) m.p. 232-235°. δH (d6DMSO) 8.14 (1H, s), 7.93 (1H, d, J 7.9 Hz), 7.86 (1H, d, J 9.0 Hz), 7.64 (1H, t, J 7.8 Hz), 7.47 (2H, d, J 8.1 Hz), 7.30 (2H, d, J 8.1 Hz), 6.55 (1H, br s), 6.53 (1H, br s) and 2.36 (3H, s), carboxyl proton and amino protons not observed. MS (ES, +27V) 337 (MH+, 100%);

Provenance & Evidence