Tetrahydrofuran → (5-Chloro-2-fluoro-4-((2-methyl-3-indazolylcarbonyl)amino)phenyl)acetic acid

HRID 1372743

Reaction equation

HRID 1372743 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][C:16]([C:18]2[N:19]([CH3:27])[N:20]=[C:21]3[C:26]=2[CH:25]=[CH:24][CH:23]=[CH:22]3)=[O:17])=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([O:11]CC)=[O:10])[CH:7]=1.C1COCC1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[C:3]([NH:15][C:16]([C:18]2[N:19]([CH3:27])[N:20]=[C:21]3[C:26]=2[CH:25]=[CH:24][CH:23]=[CH:22]3)=[O:17])=[CH:4][C:5]([F:14])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58778670Ethyl (5-chloro-2-fluoro-4-((2-methyl-3-indazolylcarbonyl)amino)phenyl)acetate

Product 1

HCID 17859380(5-Chloro-2-fluoro-4-((2-methyl-3-indazolylcarbonyl)amino)phenyl)acetic acidYield 340%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To ethyl (5-chloro-2-fluoro-4-((2-methyl-3-indazolylcarbonyl)amino)phenyl)acetate (390 mg, 1.00 mmol) were added THF (10 ml) and 0.25N NaOH (6.00 ml, 1.50 mmol). The resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was poured in 1N HCl (1.5 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (5-chloro-2-fluoro-4-((2-methyl-3-indazolylcarbonyl)amino)phenyl)acetic acid (1.23 g, 95%) as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-fb42eba0e7c840a88088eb6d27343210
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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