Water → HCID 69243383, compound

HRID 1878183Notes

Reaction equation

HRID 1878183 reaction equation
Cl[C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].O>CS(C)=O>[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19][NH:20][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:14])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5972502,4-DimethoxybenzylamineHCID 13385670HCID 13385670, compound

Product 1

HCID 69243383HCID 69243383, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2-chloro-6-fluoro-3-methoxyquinoxaline (4.00 g, 18.8 mmol) dissolved in dimethylsulfoxide (40 ml), 2,4-dimethoxybenzylamine (7.86 g, 47.0 mmol) was added at room temperature. The mixture was stirred at room temperature for 24 hours and then water was added thereto. The product was extracted with ethyl acetate and the organic layer was washed with water and dried over MgSO4. After concentration under the reduced pressure, the crude product was purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (6:1) mixture and concentration gave 4.45 g of the titled compound (yield, 92%).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration under the reduced pressure
  5. customthe crude product was purified by SiO2 column chromatography
  6. extractionExtraction of the residue
  7. concentrationwith a n-hexane:ethyl acetate (6:1) mixture and concentration

Sources & evidence

ORD record
ord-d0e485b9c74941eda8b4d6ad2f6b18d2
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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