3-n-Butyl-1-[5-(ethoxycarbonyl)-2-(trifluoromethyl)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile → 3-n-Butyl-1-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile

HRID 257582Notes

Reaction equation

HRID 257582 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23](=[O:26])(=[O:25])[NH2:24])=[CH:13][C:12]=2[F:27])=[C:8]([C:28]#[N:29])[N:7]([C:30]2[CH:35]=[C:34]([C:36](OCC)=[O:37])[CH:33]=[CH:32][C:31]=2[C:41]([F:44])([F:43])[F:42])[N:6]=1)[CH2:2][CH2:3][CH3:4]>C(N)CCC>[CH2:1]([C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23](=[O:25])(=[O:26])[NH2:24])=[CH:13][C:12]=2[F:27])=[C:8]([C:28]#[N:29])[N:7]([C:30]2[CH:35]=[C:34]([C:36](=[O:37])[NH:6][CH2:5][CH2:1][CH2:2][CH3:3])[CH:33]=[CH:32][C:31]=2[C:41]([F:42])([F:44])[F:43])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 197831793-n-Butyl-1-[5-(ethoxycarbonyl)-2-(trifluoromethyl)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile

Product 1

HCID 197832183-n-Butyl-1-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A solution of 3-n-butyl-1-[5-(ethoxycarbonyl)-2-(trifluoromethyl)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile (from Step K) in n-butylamine (approximately 10 mL of amine per mmole of ester) is heated in a sealed tube at 120° C. overnight. Volatiles are removed by evaporation, and the residue is chromatographed on silica gel (elution with CH2Cl2 --MeOH) to provide the title compound.

Workup

  1. customVolatiles are removed by evaporation
  2. customthe residue is chromatographed on silica gel (elution with CH2Cl2 --MeOH)

Sources & evidence

ORD record
ord-bed78f84266d4a1185e9094513e3930d
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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