Sodium Hydroxide → HCID 70664944, compound

HRID 1403637Notes

Reaction equation

HRID 1403637 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH3:31])[C:10]2[C:11]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][C:16]([C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=3)[CH2:5][CH2:4]1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH3:31])[C:10]2[C:11]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=3)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70664915HCID 70664915, compound

Product 1

HCID 70664944HCID 70664944, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[(1-ethylpiperidin-4-yl)(methyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylate (53 mg, 0.12 mmol) in methanol (30 mL) was added sodium hydroxide (26.5 mg, 0.66 mmol), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (10 mL), and adjusted to pH 5 with HCl (3N) to give the precipitate, which was collected by filtration to afford 3-[(1-ethylpiperidin-4-yl)(methyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid as a light yellow solid (35.2 mg, 69%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (10 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-01debfdf3f1842b7a14d7aaaa59fa176
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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