Water → 1-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-1H-[1,2,3]triazole-4-carboxylic acid

HRID 2067240Notes

Reaction equation

HRID 2067240 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([C:17](=[O:34])[C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=4[F:32])=[CH:20][C:19]=3[Cl:33])[CH:11]=2)[CH:9]=1)=[O:4].O.[Li+].[OH-].CCOC(C)=O>CO.Cl>[Cl:33][C:19]1[CH:20]=[C:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[CH:22]=[CH:23][C:18]=1[C:17]([C:12]1[CH:11]=[C:10]([N:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=[N:7]2)[CH:15]=[CH:14][C:13]=1[CH3:16])=[O:34]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 115402951-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

Product 1

HCID 115256511-{3-[2-Chloro-4-(2,4-difluoro-phenylamino)-benzoyl]-4-methyl-phenyl}-1H-[1,2,3]triazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A suspension of compound 132 (100 mg, 0.21 mmol) in MeOH (5.0 mL) was added H2O (0.6 mL) and LiOH (25 mg, 1.0 mmol) and the resulting reaction mixture was refluxed for 1 h. EtOAc was added to the reaction and pH adjuste to 1-2 with concentrated HCl (37%, 6 drops). The organic phase was separated and the aqueous layer was extracted with more EtOAc. The organic phases were collected and washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo to give the title compound as white solid.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 1 h
  3. customThe organic phase was separated
  4. extractionthe aqueous layer was extracted with more EtOAc
  5. customThe organic phases were collected
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76739d4de04f41649d3265a763ce7d95
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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