Water → 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid

HRID 1403494Notes

Reaction equation

HRID 1403494 reaction equation
[CH:1]([N:4]([CH3:29])[C:5]1[C:6]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][CH:23]=[C:22]3[CH3:28])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[CH:1]([N:4]([CH3:29])[C:5]1[C:6]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][CH:23]=[C:22]3[CH3:28])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664626methyl 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate

Product 1

HCID 706650623-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acidYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate (80 mg, 0.21 mmol) in MeOH (10 mL) was added sodium hydroxide (52 mg, 0.29 mmol) and water (1 mL). The resulting solution was stirred for 2 h at room temperature and concentrated under vacuum. The residue was dissolved in water (3 mL) and adjusted to pH 6 with hydrochloric acid (1N). The solids were collected by filtration to afford 3-(isopropyl(methyl)amino)-2-(3-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid as a yellow solid (45.8 mg, 59%).

Workup

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

Sources & evidence

ORD record
ord-cc200d1865894eb29d93620d481890ba
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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