Sodium Hydroxide → 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid

HRID 1403459Notes

Reaction equation

HRID 1403459 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[C:20]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:27]([O:29]C)=[O:28])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[C:20]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:27]([OH:29])=[O:28])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70665283methyl 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate

Product 1

HCID 706648652-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acidYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (140 mg, 0.35 mmol) in methanol (30 mL) and water (2 mL) was added sodium hydroxide (56 mg, 1.40 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (30 mL) and adjusted to pH 5 with acetic acid. The solids were collected by filtration to afford 2-(2-methyl-1H-indol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid as a light yellow solid (100 mg, 74%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-bfd259ebc12547c5b3d42cf3d4e18045
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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