Hydrochloric Acid → 2-(6-Chloro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid

HRID 1403378Notes

Reaction equation

HRID 1403378 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[CH:6]=[C:7]([C:9]3[C:18]([N:19]([CH3:23])[CH:20]([CH3:22])[CH3:21])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:24]([O:26]C)=[O:25])[CH:15]=4)[N:10]=3)[O:8][C:4]=2[CH:3]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[CH:6]=[C:7]([C:9]3[C:18]([N:19]([CH3:23])[CH:20]([CH3:22])[CH3:21])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:24]([OH:26])=[O:25])[CH:15]=4)[N:10]=3)[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70665053Methyl 2-(6-chloro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate

Product 1

HCID 706648942-(6-Chloro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acidYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl 2-(6-chloro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (60 mg, 0.15 mmol) in methanol (20 mL) and water (1 mL) was added sodium hydroxide (16 mg, 0.40 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure to afford a residue, which was dissolved in water (20 mL), adjusted the pH to 6 with 3N HCl and filtered to give 2-(6-chloro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid as a light yellow solid (25.2 mg, 43%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto afford a residue, which
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c50737226ffe458daa99224059b0b4fc
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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