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Water → [5-Methyl-2-({6-methoxy-7-[2-(4-tetrahydro-1-pyrrolylpiperidino)ethoxy]-4-quinolyl}oxy)phenyl](phenyl)methanone

HRID 228655
Notes
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Reaction equation

HRID 228655 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:24])=[CH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:31][CH3:32].[N:33]1([CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:41]4[CH2:42][CH2:43][CH:38]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[CH2:39][CH2:40]4)=[C:6]([O:31][CH3:32])[CH:7]=3)[N:12]=[CH:11][CH:10]=2)=[C:17]([C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 787034-(1-Pyrrolidinyl)piperidineHCID 57756412(2-{[7-(2-Chloroethoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone

Product 1

HCID 57756473[5-Methyl-2-({6-methoxy-7-[2-(4-tetrahydro-1-pyrrolylpiperidino)ethoxy]-4-quinolyl}oxy)phenyl](phenyl)methanoneYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(2-{[7-(2-Chloroethoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone (96 mg), 4-(1-pyrrolidinyl)piperidine (97 mg), and potassium carbonate (145 mg) were suspended in N,N-dimethylformamide (3 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. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (43 mg, yield 41%).

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-4d15e8b504e94aae86f879ddc4f2f3a2
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes