4-Methoxycarbonyl-3-nitrobenzhydrazide → methyl 4-[[1-[1-(4-tert-butylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethylamino]carbamoyl]-2-nitrobenzoate

HRID 555621Notes

Reaction equation

HRID 555621 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([OH:16])=[C:14]([C:17](=O)[CH3:18])[C:13]([CH3:20])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][C:26]=1[N+:35]([O-:37])=[O:36])=[O:24]>CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14](=[C:17]([NH:32][NH:31][C:29](=[O:30])[C:28]3[CH:33]=[CH:34][C:25]([C:23]([O:22][CH3:21])=[O:24])=[C:26]([N+:35]([O-:37])=[O:36])[CH:27]=3)[CH3:18])[C:13]([CH3:20])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 669863564-Methoxycarbonyl-3-nitrobenzhydrazideHCID 178466979HCID 178466979, compound

Product 1

HCID 178498002methyl 4-[[1-[1-(4-tert-butylphenyl)-3-methyl-5-oxopyrazol-4-ylidene]ethylamino]carbamoyl]-2-nitrobenzoateYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF solution (2.0 mL) of 1-(1-(4-tert-butylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-ethanone (54.5 mg, 0.20 mmol) and 4-methoxycarbonyl-3-nitrobenzhydrazide (47.8 mg, 0.20 mmol) was heated at 110° C. for 6 hours After removing solvent, the residue was purified by column chromatography to give the title compound (53.8 mg, 55%) as a brown solid.

Workup

  1. customAfter removing solvent
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a584e8e67c2f42baa29df2864aa4f2c0
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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