Water → HCID 22667179, compound

HRID 1375907Notes

Reaction equation

HRID 1375907 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([NH:20][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])=[C:15]([CH3:27])[CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].[Br:36][CH2:37][CH2:38][CH2:39]Br.O>CN(C)C=O>[Br:36][CH2:37][CH2:38][CH2:39][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([NH:20][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])=[C:15]([CH3:27])[CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 135674223HCID 135674223, compound

Product 1

HCID 22667179HCID 22667179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A starting compound (N-{4-[(7-hydroxy-6-methoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}-N′-propylurea, 80 mg), potassium carbonate (138 mg), and 1,3-dibromopropane(0.10 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-(3-bromopropoxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylphenyl)-N′-propylurea). The intermediate, potassium carbonate (138 mg), and 1-methylpiperazine (0.055 ml) were dissolved in N,N-dimethylformamide (1 ml), and the mixture 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 33 mg (yield 31%) 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-928b33c343a94d1a92f0612eef68cefd
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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