Water → HCID 70665105, compound

HRID 1403413Notes

Reaction equation

HRID 1403413 reaction equation
[S: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]=[CH:2]1.[OH-].[Na+].O>CO>[S: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]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665169HCID 70665169, compound

Product 1

HCID 70665105HCID 70665105, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(1,3-benzothiazol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (100 mg, 0.25 mmol) in methanol (15 mL) was added sodium hydroxide (30.0 mg, 0.75 mmol) and water (1 mL). The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (15 mL) and adjusted pH to 5 with hydrochloric acid (3 N). The solids were collected by filtration to afford 2-(1,3-benzothiazol-5-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid as a yellow solid (80 mg, 82%).

Workup

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

Sources & evidence

ORD record
ord-597c2f9c73b74840a579b38727052b9a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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