Water → N-(2,4-Difluorophenyl)-N'-[4-({6-methoxy-7-[2-(1H-1,2,3-triazol-1-yl)ethoxy]-4-quinolyl}oxy)-2,5-dimethylphenyl]urea

HRID 1008474Notes

Reaction equation

HRID 1008474 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([OH:33])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:15][C:14]=1[CH3:34])=[O:11].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:52][CH2:53][N:54]2[CH:58]=[CH:57][N:56]=[N:55]2)(=O)=O)=CC=1.O>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH2:52][CH2:53][N:54]4[CH:58]=[CH:57][N:56]=[N:55]4)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:15][C:14]=1[CH3:34])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonateHCID 135674215N-(2,4-difluorophenyl)-N'-{4-[(7-hydroxy-6-methoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}urea

Product 1

HCID 22667214N-(2,4-Difluorophenyl)-N'-[4-({6-methoxy-7-[2-(1H-1,2,3-triazol-1-yl)ethoxy]-4-quinolyl}oxy)-2,5-dimethylphenyl]ureaYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A starting compound (N-(2,4-difluorophenyl)-N′-{4-[(7-hydroxy-6-methoxy-4-quinolyl)oxy]-2,5-dimethyl-phenyl}urea, 93 mg), potassium carbonate (138 mg), and 2-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzene-sulfonate (52 mg) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at 80° C. for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC by development with chloroform/methanol to give 33 mg (yield 30%) of the title compound.

Workup

  1. extractionthe mixture was extracted with chloroform-propanol (3/1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-c932c5acee7a469d8a9c2f7e27b7f5ee
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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