Water → HCID 70665072, compound

HRID 1403504Notes

Reaction equation

HRID 1403504 reaction equation
[CH:1]1([N:4]([CH3:29])[C:5]2[C:6]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH3:28])=[CH:22]4)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1.[OH-].[Na+].O>CO>[CH:1]1([N:4]([CH3:29])[C:5]2[C:6]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23]([CH3:28])=[CH:22]4)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664994HCID 70664994, compound

Product 1

HCID 70665072HCID 70665072, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[cyclopropyl(methyl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylate (74.7 mg, 0.19 mmol) in methanol (30 ml) was added NaOH (32 mg, 0.80 mmol), water (1 ml) with stirring overnight at room temperature. The resulting solution was extracted ethyl acetate (2×50 ml), and adjusted pH to 5 with AcOH. The resulting solution was extracted with ethyl acetate (3×30 ml), dried over anhydrous sodium sulfate, concentrated under vacuum to give a residue, which was purified via silica gel chromatography (20% methanol in ethyl acetate) to afford 3-[cyclopropyl(methyl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carboxylic acid as a yellow solid (13.6 mg, 19%).

Workup

  1. extractionThe resulting solution was extracted ethyl acetate (2×50 ml)
  2. extractionThe resulting solution was extracted with ethyl acetate (3×30 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified via silica gel chromatography (20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-38e6e746e88b43b1925c37d93b89a19c
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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