Water → (S)-2-(2,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403572Notes

Reaction equation

HRID 1403572 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([N:19]2[CH2:23][CH2:22][CH2:21][C@@H:20]2[CH3:24])=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:25]([O:27]C)=[O:26])[CH:15]=2)[N:10]=1.[OH-].[Na+].O>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([N:19]2[CH2:23][CH2:22][CH2:21][C@@H:20]2[CH3:24])=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:25]([OH:27])=[O:26])[CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665337(S)-methyl 2-(2,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664901(S)-2-(2,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-(2,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (100 mg, 0.39 mmol) in MeOH (20 mL) was added sodium hydroxide (63 mg, 1.57 mmol) and water (2 mL). The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (2 mL) and adjusted to pH 6 with hydrochloric acid (1N). The solids were collected by filtration to afford (S)-2-(2,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid as a brown solid (82.4 mg, 86%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (2 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-abf32194b49b45239689445a7e591279
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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