p-Toluenesulfonic acid monohydrate → 5-[[1-[1-(3,4-dimethylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethylamino]carbamoyl]-N-propan-2-ylthiophene-2-carboxamide

HRID 913376Notes

Reaction equation

HRID 913376 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH:8]=2)[N:5]=[C:4]([CH3:15])[C:3]=1[C:16](=O)[CH3:17].[CH3:19][CH:20]([NH:22][C:23]([C:25]1[S:26][C:27]([C:30]([NH:32][NH2:33])=[O:31])=[CH:28][CH:29]=1)=[O:24])[CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH:20]([NH:22][C:23]([C:25]1[S:26][C:27]([C:30]([NH:32][NH:33][C:16](=[C:3]2[C:2](=[O:1])[N:6]([C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH:8]=3)[N:5]=[C:4]2[CH3:15])[CH3:17])=[O:31])=[CH:28][CH:29]=1)=[O:24])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576881055-hydrazinocarbonylthiophene-2-carboxylic Acid 2-propylamideHCID 178466978HCID 178466978, compound

Product 1

HCID 1784338705-[[1-[1-(3,4-dimethylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethylamino]carbamoyl]-N-propan-2-ylthiophene-2-carboxamideYield 43%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

1-(5-Hydroxy-3-methyl-1-(3,4-dimethylphenyl)-1H-pyrazol-4-yl)-ethanone (30 mg, 0.123 mmol, synthesized in accordance with patent document 25), 5-hydrazinocarbonyl-thiophene-2-carboxylic acid 2-propylamide prepared in Reference Synthetic Example 1 and p-toluenesulfonic acid monohydrate (2 mg) in isopropanol (1 mL) were heated at 90° C. overnight under reflux. After cooling, chloroform-ether was added, and the resulting crystals were collected by filtration, washed with chloroform-ether and dried to give 24 mg of the desired product (yield 43%).

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with chloroform-ether
  5. customdried

Sources & evidence

ORD record
ord-a6713ef7ea584f5a98e104e4ce0a5af2
Source dataset
uspto-grants-2011_09
Patent number
US08026368B2

Reaction notes

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