Sodium Hydroxide → HCID 70664732, compound

HRID 1403435Notes

Reaction equation

HRID 1403435 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]4[CH2:24][CH2:23][CH2:22][C@@H:21]4[CH2:25][O:26][CH3:27])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:28]([O:30]C)=[O:29])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+]>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]4[CH2:24][CH2:23][CH2:22][C@@H:21]4[CH2:25][O:26][CH3:27])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:28]([OH:30])=[O:29])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664831HCID 70664831, compound

Product 1

HCID 70664732HCID 70664732, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(1H-indol-5-yl)-3-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinoxaline-6-carboxylate (200 mg, 0.48 mmol) in methanol (35.0 mL) and water (1.0 mL) was added sodium hydroxide (76.9 mg, 1.92 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (30.0 mL), adjusted pH to 4 with HCl (3N) to give the precipitate, which was collected by filtration to afford 2-(1H-indol-5-yl)-3-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinoxaline-6-carboxylic acid (80 mg, 41%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30.0 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6885e8da6d84465ba54aae2101bf9532
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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