Dimethyl Sulfoxide → 5-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid

HRID 2422807Notes

Reaction equation

HRID 2422807 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.N1C=CC(CN[C:29]([C:31]2[S:32][C:33]([C:36]([NH:38][NH2:39])=[O:37])=[CH:34][CH:35]=2)=[O:30])=CC=1.CS(C)=[O:42]>>[OH:1][C:2]1[C:3]([C:18](=[N:39][NH:38][C:36]([C:33]2[S:32][C:31]([C:29]([OH:30])=[O:42])=[CH:35][CH:34]=2)=[O:37])[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

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 576881445-(hydrazinecarbonyl)-N-(pyridine-4-ylmethyl)thiophene-2-carboxamideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 723600145-{1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic AcidYield 56%

Procedure

1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (50 mg, 0.18 mmol) in dimethyl sulfoxide (0.88 mL) was heated with 5-hydrazinocarbonylthiophene-2-carboxylic acid 4-picolylamide prepared in Reference Synthetic Example 4 at 100° C. for 24 hours. The solvent was evaporated, and the residue was washed with water and chloroform to give 54 mg of the desired product (yield 56%).

Workup

  1. customprepared in Reference Synthetic Example 4 at 100° C. for 24 hours
  2. customThe solvent was evaporated
  3. washthe residue was washed with water and chloroform

Sources & evidence

ORD record
ord-5caac0f08cdc4151879f5ad32e867764
Source dataset
uspto-grants-2011_06
Patent number
US07960425B2

Reaction notes

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