Hydrochloric Acid → 2-(Benzofuran-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid

HRID 1403297Notes

Reaction equation

HRID 1403297 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[C:19]([N:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:25]([O:27]C)=[O:26])[CH:16]=3)[N:11]=2)=[CH:2]1.[OH-].[Na+].Cl>O1CCCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[C:19]([N:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:25]([OH:27])=[O:26])[CH:16]=3)[N:11]=2)=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 60171603Methyl 2-(benzofuran-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 601983322-(Benzofuran-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acidYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(benzofuran-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (100 mg, 0.27 mmol) in tetrahydrofuran (20 mL) and water (1 mL) was added sodium hydroxide (105 mg, 2.62 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure to afford a residue, which was dissolved in water (10 mL), the pH was adjusted to 6 with HCl (3N) and filtered to give 2-(benzofuran-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (35.7 mg, 37%).

Workup

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

Sources & evidence

ORD record
ord-bef92e6906424c71a434bc2a69e16c29
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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