Tetrahydrofuran → (3-Chloro-4-((1-methyl-3-indazolylcarbonyl)amino)phenyl)acetic acid

HRID 1372745

Reaction equation

HRID 1372745 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([O:24]C)=[O:23])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[N:12]=1)=[O:10].C1COCC1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[N:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58778393Methyl (3-chloro-4-((1-methyl-3-indazolylcarbonyl)amino)phenyl)acetate

Product 1

HCID 17858964(3-Chloro-4-((1-methyl-3-indazolylcarbonyl)amino)phenyl)acetic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To methyl (3-chloro-4-((1-methyl-3-indazolylcarbonyl)amino)phenyl)acetate (1.08 g, 3.02 mmol) were added THF (30 ml) and 0.25N NaOH (18.1 ml, 4.53 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was poured in 1N HCl (5.0 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give (3-chloro-4-((1-methyl-3-indazolylcarbonyl)amino)phenyl)acetic acid (0.99 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-cfdf65ddbf564163a331a71c8e55848f
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

Loading…