Water → HCID 22667198, compound

HRID 1375906Notes

Reaction equation

HRID 1375906 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:27])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:9][C:8]=1[CH3:28])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:35][CH2:36][CH2:37]Br.O>CN(C)C=O>[Br:35][CH2:36][CH2:37][O:27][C:21]1[CH:20]=[C:19]2[C:24]([C:15]([O:14][C:10]3[C:11]([CH3:13])=[CH:12][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[C:8]([CH3:28])[CH:9]=3)=[CH:16][CH:17]=[N:18]2)=[CH:23][C:22]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 135674222HCID 135674222, compound

Product 1

HCID 22667198HCID 22667198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A starting compound (N-ethyl-N′-{4-[(7-hydroxy-6-methoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}urea, 76 mg), potassium carbonate (138 mg), and 1,2-dibromoethane (0.085 ml) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at room temperature for 18 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 washed with ether to give an intermediate (N-(4-{[7-(2-bromoethoxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylphenyl)-N′-ethylurea). The intermediate, potassium carbonate (138 mg), and morpholine (0.044 ml) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at room temperature for 18 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 72 mg (yield 73%) 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. washThe residue was washed with ether

Sources & evidence

ORD record
ord-6efb4a35de284334b8e5a0a8526e8498
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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