Potassium Carbonate → Fruquintinib

HRID 455919Notes

Reaction equation

HRID 455919 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:16][C:17]1[CH:30]=[CH:29][C:20]2[C:21]([C:25]([NH:27][CH3:28])=[O:26])=[C:22]([CH3:24])[O:23][C:19]=2[CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[O:16][C:17]1[CH:30]=[CH:29][C:20]2[C:21]([C:25]([NH:27][CH3:28])=[O:26])=[C:22]([CH3:24])[O:23][C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 167551736-Hydroxy-N,2-dimethylbenzofuran-3-carboxamide

Product 1

HCID 44480399FruquintinibYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-6,7-dimethoxyquinazoline (1 equiv.) in 2 ml CH3CN were added 6-hydroxy-N,2-dimethylbenzofuran-3-carboxamide (1 equiv.) and K2CO3 (1.5 equiv.). The mixture was refluxed under stirring for 10 hr. After the solvent was evaporated, the residue was washed with water, dried over MgSO4, filtered, concentrated, and purified by column chromatography to give the title compound in a yield of 85%.

Workup

  1. temperatureThe mixture was refluxed
  2. customAfter the solvent was evaporated
  3. washthe residue was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-3f12350b111642c180e254d65fb75e56
Source dataset
uspto-grants-2013_07
Patent number
US08497372B2

Reaction notes

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