Water → HCID 178461408, compound

HRID 1403529Notes

Reaction equation

HRID 1403529 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([N:20]4[CH2:24][CH2:23][CH2:22][C@@H:21]4[CH3:25])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:26]([O:28]C)=[O:27])[CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[N:3]=[N:2]1.[OH-].[Na+].O>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]([N:20]4[CH2:24][CH2:23][CH2:22][C@@H:21]4[CH3:25])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:26]([OH:28])=[O:27])[CH:16]=4)[N:11]=3)=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178497313HCID 178497313, compound

Product 1

HCID 178461408HCID 178461408, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-(1H-benzo[d][1,2,3]triazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (130 mg, 0.33 mmol) in methanol (30 mL) was added sodium hydroxide (40.2 mg, 1.00 mmol) and water (1 mL) with stirring for overnight at room temperature. The resulting mixture was concentrated under vacuum and dissolved in water (25 mL), and adjusted to pH 4 with HCl (3N) to give the precipitate, which was collected by filtration to afford (S)-2-(1H-benzo[d][1,2,3]triazol-5-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (90.3 mg, 72%).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutiondissolved in water (25 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a110521f8b8d436a9154b3adfaefb9b8
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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