Water → HCID 136414049, compound

HRID 1403517Notes

Reaction equation

HRID 1403517 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])[C:8]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[CH:15]4)=[N:9]2)=[CH:4][C:3]=1[C:27]([O:29]C)=[O:28].[OH-].[Na+].O>CO>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])[C:8]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[CH:15]4)=[N:9]2)=[CH:4][C:3]=1[C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 136414048HCID 136414048, compound

Product 1

HCID 136414049HCID 136414049, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 7-hydroxy-2-(1H-indazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (120 mg, 0.30 mmol) in methanol (10 ml) was added NaOH (48 mg, 1.27 mmol) and water (1 ml). The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (15 ml) and adjusted to pH 5 with hydrochloric acid (1N). The solids were collected by filtration to afford (S)-7-hydroxy-2-(1H-indazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (65.6 mg, 56%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (15 ml)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-cf84243f70f74e49a1b2dc9b9a121303
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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