Water → {2-[(7-{4-[(2-Hydroxyethyl)amino]butoxy}-6-methoxy-4-quinolyl)oxy]-5-methylphenyl}(phenyl)methanone

HRID 228668Notes

Reaction equation

HRID 228668 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([O:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:33][CH3:34].[C:35](=[O:38])([O-])[O-].[K+].[K+].O.[CH3:42][N:43](C)C=O>>[OH:38][CH2:35][CH2:42][NH:43][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([O:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:33][CH3:34]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 57756358(2-{[7-(4-Chlorobutoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone2×

Product 1

HCID 57756528{2-[(7-{4-[(2-Hydroxyethyl)amino]butoxy}-6-methoxy-4-quinolyl)oxy]-5-methylphenyl}(phenyl)methanoneYield 51%

Conditions

Temperature
80 °C

Procedure

(2-{[7-(4-Chlorobutoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone (compound 142) (60 mg), 4-aminoethanol (24 mg), and potassium carbonate (90 mg) were suspended in N,N-dimethylformamide (2 ml), and the suspension was stirred at 80° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate, and the solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (33 mg, yield 51%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-dd8f811db52c4bd19928d6fba071d728
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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