Water → HCID 60198404, compound

HRID 1403350Notes

Reaction equation

HRID 1403350 reaction equation
[S:1]1[C:5]([C:6]2[C:15]([N:16]([CH:18]([CH3:20])[CH3:19])[CH3:17])=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:21]([O:23]C)=[O:22])[CH:12]=3)[N:7]=2)=[CH:4][C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2.[OH-].[Na+].O>O1CCCC1>[S:1]1[C:5]([C:6]2[C:15]([N:16]([CH:18]([CH3:20])[CH3:19])[CH3:17])=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:21]([OH:23])=[O:22])[CH:12]=3)[N:7]=2)=[CH:4][C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665308HCID 70665308, compound

Product 1

HCID 60198404HCID 60198404, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(benzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (140 mg, 0.36 mmol) in tetrahydrofuran (25 mL) was added sodium hydroxide (43.2 mg, 1.08 mmol) and water (2 mL) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (20 mL) and adjusted to pH 5 with hydrochloric acid (3 N). The solids were collected by filtration to afford 2-(benzo[b]thiophen-2-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a yellow solid (80 mg, 59%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (20 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-434e8436c6ac464b9ae267d69f793ff0
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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