5-(hydrazinecarbonyl)-N-(pyridine-4-ylmethyl)thiophene-2-carboxamide → 5-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid 4-picolylamide

HRID 2422809Notes

Reaction equation

HRID 2422809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=O)[CH3:16])[C:10]=2[OH:18])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([C:34]([NH:36][NH2:37])=[O:35])=[CH:32][CH:33]=2)=[O:28])=[CH:21][CH:20]=1>CS(C)=O>[N:19]1[CH:20]=[CH:21][C:22]([CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([C:34]([NH:36][N:37]=[C:15]([C:11]3[C:10]([OH:18])=[C:9]([C:4]4[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=4)[N:13]([CH3:14])[N:12]=3)[CH3:16])=[O:35])=[CH:32][CH:33]=2)=[O:28])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 576881445-(hydrazinecarbonyl)-N-(pyridine-4-ylmethyl)thiophene-2-carboxamideHCID 602067801-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone

Product 1

HCID 765978495-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidenehydrazinocarbonyl}thiophene-2-carboxylic Acid 4-picolylamideYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-[5-(3,4-Dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (40 mg, 0.14 mmol) in dimethyl sulfoxide (1.0 mL) was mixed with 5-hydrazinocarbonylthiophene-2-carboxylic acid 4-picolylamide (39 mg, 0.14 mmol) prepared in Reference Synthetic Example 4 and left at 100° C. for 10.5 hours. The solvent was evaporated, and the residue was dissolved in chloroform (1.0 mL). After addition of n-hexane (2.0 mL), the resulting crystals were recovered by filtration to give 40 mg of the desired product (yield 53%).

Workup

  1. customprepared in Reference Synthetic Example 4
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in chloroform (1.0 mL)
  4. additionAfter addition of n-hexane (2.0 mL)
  5. filtrationthe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-0ff30061994047c8b0a7446172daecc5
Source dataset
uspto-grants-2011_06
Patent number
US07960425B2

Reaction notes

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