Water → (S)-2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403539Notes

Reaction equation

HRID 1403539 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[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:23][C@@H:22]3[CH3:33])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:34]([O:36]C)=[O:35])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2.[OH-].[Na+].O>CO>[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[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:23][C@@H:22]3[CH3:33])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:34]([OH:36])=[O:35])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664686(S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664873(S)-2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acidYield 30.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylate (150 mg, 0.30 mmol) in methanol (20 ml) was added sodium hydroxide (36 mg, 0.90 mmol) and water (1 ml) The resulting solution was stirred overnight at room temperature and the mixture was concentrated under vacuum dissolved in water (30 ml), adjusted to pH 5 with hydrochloric acid (3N) to give the precipitate, which was collected by filtration to afford (S)-2-(2-methyl-1H-indol-5-yl)-3-(2-methyl-4-(pyridin-2-yl)piperazin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (44 mg, 30%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 ml)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a0208c4e0d744dea937d9aa64cbd061a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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