Sodium Hydroxide → 5-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

HRID 522108Notes

Reaction equation

HRID 522108 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[C:24]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([O:20]CC)=[O:19])[CH:8]=1)=[O:5].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:26]=[C:25]([Cl:27])[C:24]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[C:9]([C:18]([OH:20])=[O:19])[CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118497079ethyl 5-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 1184970945-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 5-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Example 116, 822 mg, 1.65 mmol) in ethanol (15 mL) was added 2M aqueous sodium hydroxide (4.1 mL, 8.23 mmol) and the reaction was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo. The residue was diluted with water (25 mL) and neutralised with 2M aqueous hydrochloric acid. The resultant solid was filtered, washed with water and dried in vacuo to afford the title compound as a white solid (700 mg, 90%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with water (25 mL)
  3. filtrationThe resultant solid was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bd9183d09069478ab6c5ad9986c2fdcf
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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