Sodium Hydroxide → 5-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

HRID 522110Notes

Reaction equation

HRID 522110 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[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+]>Cl>[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[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 118497085ethyl 5-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 1184971125-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of ethyl 5-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Example 117A, 15.0 g, 32.3 mmol) in IMS (150 mL), was added 2M aqueous sodium hydroxide solution (83 mL) and the reaction stirred at room temperature for 3 hours. Aqueous hydrochloric acid solution (90 mL, 2 M) was then added. The resulting solid was collected by filtration, washed with water (10 mL) and dried under vacuum to give the title compound (12.7 g, 90%).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-681f56e0d89a49cbbf2402dadf632860
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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