5-Hydrazinocarbonylthiophene-2-carboxylic acid 2-picolylamide → 5-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic acid 2-picolylamide

HRID 2422805Notes

Reaction equation

HRID 2422805 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.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH:28][C:29]([C:31]1[S:32][C:33]([C:36]([NH:38][NH2:39])=[O:37])=[CH:34][CH:35]=1)=[O:30]>CS(C)=O>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH:28][C:29]([C:31]1[S:32][C:33]([C:36]([NH:38][N:39]=[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:37])=[CH:34][CH:35]=1)=[O:30]

Participants

4

Reactant 2

HCID 576881235-Hydrazinocarbonylthiophene-2-carboxylic acid 2-picolylamideHCID 602067901-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

Product 1

HCID 765978455-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic acid 2-picolylamideYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone (50 mg, 0.18 mmol) in dimethyl sulfoxide (1.0 mL) was heated with 5-hydrazinocarbonylthiophene-2-carboxylic acid 2-picolylamide (58 mg, 0.21 mmol) prepared in Reference Synthetic Example 2 at 110° C. for 21 hours. The solvent was evaporated, and the residue was washed with water and chloroform to give 79 mg of the desired product (yield 83%).

Workup

  1. customprepared in Reference Synthetic Example 2 at 110° C. for 21 hours
  2. customThe solvent was evaporated
  3. washthe residue was washed with water and chloroform

Sources & evidence

ORD record
ord-d09fa74d3af940f0a4f9f0dacb4a8441
Source dataset
uspto-grants-2011_06
Patent number
US07960425B2

Reaction notes

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