Sodium Hydroxide → (S)-2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403577Notes

Reaction equation

HRID 1403577 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([O:26]C)=[O:25])[CH:14]=3)[N:9]=2)=[C:4]([CH3:28])[CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]([OH:26])=[O:25])[CH:14]=3)[N:9]=2)=[C:4]([CH3:28])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664963(S)-methyl 2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664770(S)-2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acidYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (S)-methyl 2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (120 mg, 0.32 mmol) in methanol (20 mL) and water (1 mL) was added sodium hydroxide (50.7 mg, 1.27 mmol,) and the reaction was stirred overnight at room temperature. The resulting mixture was concentrated in vacuo, adjusted to pH 6 with aqueous HCl (3N), collected by filtration to afford (S)-2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (85.7 mg, 74%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b5128e727a7a48cc8a4e6ab8581bda9d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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