Water → HCID 70664689, compound

HRID 1403635Notes

Reaction equation

HRID 1403635 reaction equation
[CH:1]([N:4]([CH3:29])[C:5]1[C:6]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2].[OH-].[Na+].O>O1CCCC1>[CH:1]([N:4]([CH3:29])[C:5]1[C:6]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:27])([F:28])[F:26])=[CH:21][CH:20]=2)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665132HCID 70665132, compound

Product 1

HCID 70664689HCID 70664689, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(4-(trifluoromethyl)phenyl)quinoxaline-6-carboxylate (158.0 mg, 0.39 mmol) in tetrahydrofuran (20 mL) was added sodium hydroxide (47.0 mg, 1.18 mmol) and water (2 mL), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (20 mL) and adjusted to pH 5 with hydrochloric acid (1N). The solids were collected by filtration to afford 3-(isopropyl(methyl)amino)-2-(4-(trifluoromethyl)phenyl)quinoxaline-6-carboxylic acid as a light yellow solid (89 mg, 58%). LC/MS (ES, m/z): [M+H]+ 390.0

Workup

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

Sources & evidence

ORD record
ord-b8337c9ebc4a4258a2ff46cfa62f4a40
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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