Imidazole → Propyl 3-[7-(2-imidazol-1-yl-ethoxy)-6-methoxy-quinolin-4-yloxy]-naphthalene-2-carboxylate

HRID 228922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228922
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][CH2:29][CH2:30][CH3:31])=[O:27])=[CH: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:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].[NH:40]1[CH:44]=[CH:43][N:42]=[CH:41]1.O>CN(C)C=O>[N:40]1([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][CH2:29][CH2:30][CH3:31])=[O:27])=[CH: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:32][CH3:33])[CH:44]=[CH:43][N:42]=[CH:41]1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 23078556Propyl 3-[7-(2-chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-naphthalene-2-carboxylate2×

Produkt 1

HCID 23078520Propyl 3-[7-(2-imidazol-1-yl-ethoxy)-6-methoxy-quinolin-4-yloxy]-naphthalene-2-carboxylateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Propyl 3-[7-(2-chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-naphthalene-2-carboxylate (compound 322) (138 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (274 mg) and imidazole (101 mg) were added to the solution, and the mixture was stirred at 60° 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 pufified by thin layer chromatography using chloroform-methanol to give the title compound (105 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

Quellen und Nachweise

ORD-Eintrag
ord-64815234e54e49199c59fb623651bb7c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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