Sodium Hydroxide → HCID 60198405, compound

HRID 1403380Notes

Reaction equation

HRID 1403380 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]2[CH:6]=[C:7]([C:9]3[C:18]([N:19]4[CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:24])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:25]([O:27]C)=[O:26])[CH:15]=4)[N:10]=3)[O:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:30]=[CH:29][C:5]2[CH:6]=[C:7]([C:9]3[C:18]([N:19]4[CH2:23][CH2:22][CH2:21][C@@H:20]4[CH3:24])=[N:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:25]([OH:27])=[O:26])[CH:15]=4)[N:10]=3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664729HCID 70664729, compound

Product 1

HCID 60198405HCID 60198405, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(6-fluoro-1-benzofuran-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (78 mg, 0.19 mmol) in methanol (25 mL) and water (5 mL) was added sodium hydroxide (23 mg, 0.57 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (10 mL), adjusted to pH 5 with HCl (3N) to give the precipitate, which was collected by filtration to afford (S)-2-(6-fluorobenzofuran-2-yl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid (37.3 mg, 52%).

Workup

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

Sources & evidence

ORD record
ord-ed6adee1d2c849d98f62be9f543cd299
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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