Water → 1-(3-{7-[2-(3-Hydroxy-piperidin-1-yl)-ethoxy]-6-methoxy-quinolin-4-yloxy}-quinolin-2-yl)-ethanone

HRID 228995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228995
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[C:17]([C:26](=[O:28])[CH3:27])=[N:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].[OH:37][CH:38]1[CH2:43][CH2:42][CH2:41][NH:40][CH2:39]1.O>CN(C)C=O>[OH:37][CH:38]1[CH2:43][CH2:42][CH2:41][N:40]([CH2:2][CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([O:15][C:16]4[C:17]([C:26](=[O:28])[CH3:27])=[N:18][C:19]5[C:24]([CH:25]=4)=[CH:23][CH:22]=[CH:21][CH:20]=5)=[CH:10][CH:11]=[N:12]3)=[CH:7][C:6]=2[O:29][CH3:30])[CH2:39]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 232933-HydroxypiperidineHCID 688315601-{3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone

Produkt 1

HCID 577565211-(3-{7-[2-(3-Hydroxy-piperidin-1-yl)-ethoxy]-6-methoxy-quinolin-4-yloxy}-quinolin-2-yl)-ethanoneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-{3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone (46 mg) was dissolved in N,N-dimethylformamide (1 ml) to prepare a solution. Potassium carbonate (45 mg) and 3-hydroxypiperidine (33 mg) were added to the solution, and the mixture was stirred at 80° C. overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (37 mg, yield 70%).

Aufarbeitung

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-59e429a9af594b2ca54e09717841f90f
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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