Potassium Carbonate → N-(2-Chloro-4-{[6-methoxy-7-(4-pyridylmethoxy)-4-quinolyl]oxy}phenyl)-N'-(2,4-difluorophenyl)urea

HRID 1008480Notes

Reaction equation

HRID 1008480 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:42][C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:42][C:43]4[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 135674212N-{2-Chloro-4-[(7-hydroxy-6-methoxy-4-quinolyl)-oxy]phenyl}-N'-(2,4-difluorophenyl)urea

Product 1

HCID 22667041N-(2-Chloro-4-{[6-methoxy-7-(4-pyridylmethoxy)-4-quinolyl]oxy}phenyl)-N'-(2,4-difluorophenyl)ureaYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-{2-Chloro-4-[(7-hydroxy-6-methoxy-4-quinolyl)-oxy]phenyl}-N′-(2,4-difluorophenyl)urea (55 mg), potassium carbonate (62 mg), and 4-(chloromethyl)pyridine hydrochloride (22 mg) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at 80° C. for one hr. The solvent was removed by distillation under the reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was washed with ether to give 35 mg (yield 55%) of the title compound.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under the reduced pressure
  6. washThe residue was washed with ether

Sources & evidence

ORD record
ord-3b3319743b964705bd21791f0cc82eb6
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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