Sodium Hydroxide → HCID 70664897, compound

HRID 1403465Notes

Reaction equation

HRID 1403465 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:15]([N:16]3[CH2:20][CH2:19][CH2:18][C@@H:17]3[CH3:21])=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:22]([O:24]C)=[O:23])[CH:12]=3)[N:7]=2)=[CH:2]1.[OH-].[Na+]>CO.O>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:15]([N:16]3[CH2:20][CH2:19][CH2:18][C@@H:17]3[CH3:21])=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:22]([OH:24])=[O:23])[CH:12]=3)[N:7]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664933HCID 70664933, compound

Product 1

HCID 70664897HCID 70664897, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(furan-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (111 mg, 0.33 mmol) in methanol (20 mL) and water (1.0 mL) was added sodium hydroxide (52.9 mg, 1.32 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (10 mL), adjusted pH to 4 with HCl (3N) to give the precipitate, which was collected by filtration to afford 2-(furan-3-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid as a light yellow solid (72 mg, 68%).

Workup

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

Sources & evidence

ORD record
ord-67a245d940104cbc93b34d58236a0566
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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