2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → 5-amino-1-(3-methanesulfonyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1024605Notes

Reaction equation

HRID 1024605 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][NH2:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C(O[CH:16]=[C:17]([C:23]#[N:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>CCO>[CH2:21]([O:20][C:18]([C:17]1[CH:16]=[N:12][N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)[C:23]=1[NH2:24])=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 22034382(3-Methanesulfonylphenyl)hydrazine

Product 1

HCID 578994295-amino-1-(3-methanesulfonyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the above crude (3-methanesulfonyl-phenyl)-hydrazine (0.86 g, 4.6 mmol) and ethyl (ethoxymethylene)cyanoacetate (0.78 g, 4.6 mmol) in EtOH (23 mL) is heated at 80° C. for 2 h before removal of the solvent. The residue is purified by silica gel chromatography to provide 5-amino-1-(3-methanesulfonyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester as a light yellow solid; HPLC-MS calculated for C13H15N3O4S (M+H+) 310.1, found 310.1.

Workup

  1. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-cd03a9139ebc491f8465bfed61c425a5
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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