p-Toluenesulfonic acid → 5-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid 2-propylamide

HRID 2422806Notes

Reaction equation

HRID 2422806 reaction equation
[OH:1][C:2]1[C:3]([C:18](=O)[CH3:19])=[N:4][N:5]([CH3:17])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[CH3:21][CH:22]([NH:24][C:25]([C:27]1[S:28][C:29]([C:32]([NH:34][NH2:35])=[O:33])=[CH:30][CH:31]=1)=[O:26])[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C>[CH3:23][CH:22]([NH:24][C:25]([C:27]1[S:28][C:29]([C:32]([NH:34][N:35]=[C:18]([C:3]2[C:2]([OH:1])=[C:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)[N:5]([CH3:17])[N:4]=2)[CH3:19])=[O:33])=[CH:30][CH:31]=1)=[O:26])[CH3:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 576881055-hydrazinocarbonylthiophene-2-carboxylic Acid 2-propylamideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 765978485-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid 2-propylamideYield 42%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (50 mg, 0.18 mmol, synthesized in accordance with WO2004/108683), 5-hydrazinocarbonylthiophene-2-carboxylic acid 2-propylamide (40 mg, 0.18 mmol) prepared in Reference Synthetic Example 3 and p-toluenesulfonic acid (6 mg) were heated with 2-propanol (1.8 mL) for 14 hours with reflux. After cooling, the solvent was evaporated, and the resulting solid was washed with 2-propanol to give 36 mg of the desired product (yield 42%).

Workup

  1. temperaturewith reflux
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. washthe resulting solid was washed with 2-propanol

Sources & evidence

ORD record
ord-e346505770644f7ca2c6077e3fb0e8f8
Source dataset
uspto-grants-2011_06
Patent number
US07960425B2

Reaction notes

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