Sodium Hydroxide → HCID 70664914, compound

HRID 1403479Notes

Reaction equation

HRID 1403479 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[C:19]([N:20]3[CH2:24][CH2:23][CH2:22][C@@H:21]3[CH3:25])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:26]([O:28]C)=[O:27])[CH:16]=3)[N:11]=2)=[CH:2]1.[OH-].[Na+]>CO.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[C:19]([N:20]3[CH2:24][CH2:23][CH2:22][C@@H:21]3[CH3:25])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:26]([OH:28])=[O:27])[CH:16]=3)[N:11]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664969HCID 70664969, compound

Product 1

HCID 70664914HCID 70664914, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(1-benzofuran-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (80 mg, 0.21 mmol) in methanol (40 mL) and water (1 mL) was added sodium hydroxide (33 mg, 0.83 mmol) with stirring overnight at room temperature. The resulting mixture was concentrated under vacuum, dissolved in water (50 ml) adjusted to pH 6 with HCl (3N), and collected by filtration to give 2-(1-benzofuran-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid as a yellow solid (60.1 mg, 78%).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutiondissolved in water (50 ml)
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-00dc3a4f855945a9b259545106d09135
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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