Water → 3-[4-(5,6-Dimethyl-[2,3']bipyridin-3-yloxy)-6-methoxy-quinolin-7-yloxy]-propane-1,2-diol

HRID 228949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228949
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14]C1CO1)[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[C:20]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[N:21][C:22]([CH3:26])=[C:23]([CH3:25])[CH:24]=1.F[C:34](F)(F)[C:35]([OH:37])=O.[OH-:40].[Na+].O>C(Cl)Cl>[CH3:25][C:23]1[CH:24]=[C:19]([O:18][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH2:14][CH:35]([OH:37])[CH2:34][OH:40])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)[C:20]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[N:21][C:22]=1[CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 577565193-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,3']bipyridine2×

Produkt 1

HCID 577564743-[4-(5,6-Dimethyl-[2,3']bipyridin-3-yloxy)-6-methoxy-quinolin-7-yloxy]-propane-1,2-diolAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,3′]bipyridine (compound 348) (92 mg) was dissolved in methylene chloride (2 ml) to prepare a solution which was then brought to 0° C. Trifluoroacetic acid (1 ml) was added to the solution, and the mixture was stirred at 0° C. for 30 min. The mixture was then stirred at room temperature for 5 hr. The reaction solution was brought to 0° C., was stirred, and was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added, and the mixture was extracted with chloroform. The chloroform 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 (34 mg, yield 36%).

Aufarbeitung

  1. customto prepare a solution which
  2. customwas then brought to 0° C
  3. stirringThe mixture was then stirred at room temperature for 5 hr
  4. customwas brought to 0° C.
  5. stirringwas stirred
  6. extractionthe mixture was extracted with chloroform
  7. washThe chloroform layer was then washed with saturated brine
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-230da56d6c3349e583e1f16c44ed1817
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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