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

HRID 2422804Notes

Reaction equation

HRID 2422804 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.[CH2:21]([N:23]([CH2:35][CH3:36])[C:24]([C:26]1[S:27][C:28]([C:31]([NH:33][NH2:34])=[O:32])=[CH:29][CH:30]=1)=[O:25])[CH3:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C>[CH2:35]([N:23]([CH2:21][CH3:22])[C:24]([C:26]1[S:27][C:28]([C:31]([NH:33][N:34]=[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:32])=[CH:29][CH:30]=1)=[O:25])[CH3:36]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 57688164N,N-Diethyl-5-(hydrazinecarbonyl)thiophene-2-carboxamideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 731751295-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid DiethylamideYield 53.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (28 mg, 0.10 mmol, synthesized in accordance with WO2004/108683), 5-hydrazinocarbonylthiophene-2-carboxylic acid diethylamide (24 mg, 0.10 mmol) prepared in Reference Synthetic Example 1 and p-toluenesulfonic acid (6 mg) were heated with 2-propanol (4 mL) for 14 hours with reflux. After cooling, the solvent was evaporated, and the resulting solid was recrystallized from 2-propanol-diethyl ether-n-hexane to give 27 mg of the desired product (yield 53%).

Workup

  1. temperaturewith reflux
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customthe resulting solid was recrystallized from 2-propanol-diethyl ether-n-hexane

Sources & evidence

ORD record
ord-39ccdd806be14e8a84624b231308dd0b
Source dataset
uspto-grants-2011_06
Patent number
US07960425B2

Reaction notes

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