Sodium Hydroxide → 6-Quinoxalinecarboxylic acid, 3-[(2S)-2-methyl-1-pyrrolidinyl]-2-[5-(trifluoromethyl)-2-benzofuranyl]-

HRID 1403447Notes

Reaction equation

HRID 1403447 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8]([C:21]2[O:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:24]=3[CH:25]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19]C)=[O:18])=[CH:12][CH:11]=2.[OH-].[Na+]>CO.O>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8]([C:21]2[O:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:26][C:24]=3[CH:25]=2)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70665068HCID 70665068, compound

Product 1

HCID 706653386-Quinoxalinecarboxylic acid, 3-[(2S)-2-methyl-1-pyrrolidinyl]-2-[5-(trifluoromethyl)-2-benzofuranyl]-Yield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[(2S)-2-methylpyrrolidin-1-yl]-2-[5-(trifluoromethyl)-1-benzofuran-2-yl]quinoxaline-6-carboxylate (150 mg, 0.33 mmol) in methanol (30 mL) and water (1 mL) was added sodium hydroxide (53 mg, 1.33 mmol) with stirring overnight at room temperature. The resulting mixture was concentrated in vacuo and dissolved in water (15 mL), adjusted to pH 7 with HCl (3N). The product was collected by filtration to give 3-[(2S)-2-methylpyrrolidin-1-yl]-2-[5-(trifluoromethyl)-1-benzofuran-2-yl]quinoxaline-6-carboxylic acid as a yellow solid (72.8 mg, 50%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. dissolutiondissolved in water (15 mL)
  3. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-f47a5c9442eb40bc985cbc59e6cc3c66
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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