Sodium Hydroxide → 4-Chloro-3-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]benzoic acid

HRID 1946314Notes

Reaction equation

HRID 1946314 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[CH2:12][N:13]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[O:20])=[N:14]1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:12][N:13]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[O:20])=[N:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59547941Methyl 4-chloro-3-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]benzoate

Product 1

HCID 595479654-Chloro-3-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-chloro-3-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]benzoate (for a preparation see Intermediate 23)(0.95 g, 2.34 mmol) in methanol (20 ml) was added sodium hydroxide (2.4 ml, 4.80 mmol). The reaction was stirred for 4 h, under nitrogen, at ambient temperature. The solvent was evaporated in vacuo, and the residue partitioned between diethyl ether (60 ml) and 2N aqueous HCl (50 ml). The residue was insoluble and the diethyl ether was removed in vacuo. The aqueous suspension was filtered through a hydrophobic frit, and the residue washed with ether and dried under vacuum to give the title compound as a white solid (0.651 g);

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between diethyl ether (60 ml) and 2N aqueous HCl (50 ml)
  3. customthe diethyl ether was removed in vacuo
  4. filtrationThe aqueous suspension was filtered through a hydrophobic frit
  5. washthe residue washed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-16ece75a2abb4b6d940a2acfbac51123
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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