Water → (S)-2-(5-fluorobenzofuran-2-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid

HRID 1403543Notes

Reaction equation

HRID 1403543 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]4[CH3:26])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:27]([O:29]C)=[O:28])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:31]=1.[OH-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:19]([N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]4[CH3:26])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:27]([OH:29])=[O:28])[CH:16]=4)[N:11]=3)=[CH:7][C:6]=2[CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70665325(S)-methyl 2-(5-fluorobenzofuran-2-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylate

Product 1

HCID 70664692(S)-2-(5-fluorobenzofuran-2-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-(5-fluorobenzofuran-2-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylate (120 mg, 0.29 mmol) in MeOH (20 mL) was added sodium hydroxide (46 mg, 1.15 mmol) and water (3 mL). The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (10 mL) and adjusted to pH 5 with hydrochloric acid (1N). The solids were collected by filtration to afford (S)-2-(5-fluorobenzofuran-2-yl)-3-(2-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid (113 mg, 97%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-aa2bf99d33de47c7af721dc5dad696a8
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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