3-Amino-4-chlorophenol → N-(2-chloro-5-hydroxyphenyl)-3-oxo-2-(4-pyrazol-1-ylbenzyl)butyramide

HRID 1922093Notes

Reaction equation

HRID 1922093 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C(S[C:15](=[O:32])[CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[CH:30][CH:29]=[N:28]2)=[CH:23][CH:22]=1)[C:17](=[O:19])[CH3:18])(C)(C)C>COCCOC.FC(F)(F)C([O-])=O.[Ag+]>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=1[NH:1][C:15](=[O:32])[CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[CH:30][CH:29]=[N:28]2)=[CH:23][CH:22]=1)[C:17](=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 50700783-Amino-4-chlorophenolHCID 866423723-oxo-2-(4-pyrazol-1-ylbenzyl)thiobutyric acid S-tert-butyl ester

Product 1

HCID 86642371N-(2-chloro-5-hydroxyphenyl)-3-oxo-2-(4-pyrazol-1-ylbenzyl)butyramideYield 61.4%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Silver trifluoroacetate (1.5 g) was added, over a period of 1 hour, to a stirred solution of 3-amino-4-chlorophenol (0.67 g) and 3-oxo-2-(4-pyrazol-1-ylbenzyl)thiobutyric acid S-tert-butyl ester (1.7 g) in 1,2-dimethoxyethane (10 mL) at room temperature, and the resulting mixture was stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 3:1 by volume) to afford title compound as a brown solid (1.1 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 3:1 by volume)

Sources & evidence

ORD record
ord-3e948d9712f640d1932622b879fa0661
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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