Hydrochloric Acid → (S)-2-(2-methyl-1H-indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403502Notes

Reaction equation

HRID 1403502 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[C:20]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:27])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:28]([O:30]C)=[O:29])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]1[C:20]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:27])=[N:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:28]([OH:30])=[O:29])[CH:17]=3)[N:12]=1)=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70664932(S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70665116(S)-2-(2-methyl-1H-indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acidYield 9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of (S)-methyl 2-(2-methyl-1H-indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylate (142.1 mg, 0.34 mmol) in methanol (30 ml) was added NaOH (55 mg, 1.38 mmol) and water (2 ml). The resulting solution was stirred overnight at room temperature and concentrated under vacuum to give a residue, which was dissolved in water (20 ml), and the pH adjusted to 4 with HCl (3N). The solids were collected by filtration to afford (S)-2-(2-methyl-1H-indol-5-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (11.9 mg, 9%).

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a residue, which
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-8b25df08245843bb9c402466398933ab
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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