Sodium Hydroxide → (5-Chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetic acid

HRID 1372792Notes

Reaction equation

HRID 1372792 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:17])=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([O:11]CC)=[O:10])[CH:7]=1.[OH-].[Na+]>CO.Cl>[Cl:1][C:2]1[C:3]([NH:15][C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][N:19]=2)=[O:17])=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44606313Ethyl (5-chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetate

Product 1

HCID 17859254(5-Chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetic acidYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Ethyl (5-chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetate (531 mg, 1.41 mmol) was dissolved in methanol (50 ml). To the resulting solution was added 0.25N NaOH (12 ml, 3 mmol). The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was poured in 1N HCl (100 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure for 15 hours to give (5-chloro-2-fluoro-4-(3-indazolylcarbonylamino)phenyl)acetic acid (480 mg, 98%) as a colorless crystalline powder.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure for 15 hours

Sources & evidence

ORD record
ord-60251fd8e08b4f8a97d74fa488b643f8
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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