Water → HCID 60198477, compound

HRID 1403433Notes

Reaction equation

HRID 1403433 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]4[CH3:26])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:27]([O:29]C)=[O:28])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].O>CO.C(Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]4[CH3:26])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:27]([OH:29])=[O:28])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665083HCID 70665083, compound

Product 1

HCID 60198477HCID 60198477, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-methyl 2-(1H-indol-5-yl)-3-(3-methylmorpholino)quinoxaline-6-carboxylate (110 mg, 0.27 mmol) in methanol (15 mL) and CHCl3 (5 mL) was added NaOH (32.4 mg, 0.81 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 to pH 5 with hydrochloric acid (1N). The solids were collected by filtration to afford (S)-2-(1H-indol-5-yl)-3-(3-methylmorpholino)quinoxaline-6-carboxylic acid as a yellow solid (81 mg, 76%).

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-1f9d319c49644be8a21f29d40a773b68
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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