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

HRID 582018Notes

Reaction equation

HRID 582018 reaction equation
[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].[C:17]([C:20]1[CH:21]=[C:22]([NH:26][NH2:27])[CH:23]=[CH:24][CH:25]=1)([OH:19])=[O:18].C(N(CC)CC)C.C(O)(=O)C>C(Cl)Cl.CO>[NH2:2][C:1]1[N:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:17]([OH:19])=[O:18])[CH:21]=2)[N:27]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27365213-Hydrazinobenzoic acidHCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Product 1

HCID 543577715-Amino-1-(3-carboxyphenyl)-3-(4-tolyl)pyrazole-4-carboxamideYield 50.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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%);

Sources & evidence

ORD record
ord-7709073fabb34bf5a310bc1bf99266e9
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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