Sodium Hydroxide → HCID 70664949, compound

HRID 1403363Notes

Reaction equation

HRID 1403363 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[CH:6]=[C:7]([C:9]3[C:18]([N:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:25])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:26]([O:28]C)=[O:27])[CH:15]=4)[N:10]=3)[O:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:31]=[CH:30][C:5]2[CH:6]=[C:7]([C:9]3[C:18]([N:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:25])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:26]([OH:28])=[O:27])[CH:15]=4)[N:10]=3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 60171728HCID 60171728, compound

Product 1

HCID 70664949HCID 70664949, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(6-fluoro-1-benzofuran-2-yl)-3-[(2S)-2-methylpiperidin-1-yl]quinoxaline-6-carboxylate (50 mg, 0.12 mmol) in methanol (25 mL) and water (5 mL) was added sodium hydroxide (14.4 mg, 0.36 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (30 mL), adjusted pH to 5 with HCl (3N) to give the precipitate, which was collected by filtration to afford 2-(6-fluoro-1-benzofuran-2-yl)-3-[(2S)-2-methylpiperidin-1-yl]quinoxaline-6-carboxylic acid (36.6 mg, 76%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (30 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-77c3e2ad5dfb4332ab48bfd2325f2e8a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…