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Potassium Carbonate → 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)4-(quinolin-7-yloxy)quinazoline

HRID 1791685
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1791685
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1.[OH-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 112450614-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazolineHCID 1354268667-Hydroxyquinoline

Produkt 1

HCID 98254556-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)4-(quinolin-7-yloxy)quinazolineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (200 mg, 0.57 mmol), potassium carbonate (106 mg, 0.77 mmol) and 7-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The reaction mixture was treated with 1.0 N aqueous sodium hydroxide solution (40 ml) and allowed to stir at ambient temperature for a few minutes. The reaction mixture was extracted 4 times with ethyl acetate and the organic extracts washed with water and brine. The organic extracts were dried over magnesium sulphate, filtered and the solvent removed by evaporation. The residue was triturated with ether/isohexane, filtered and dried to give 6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)4-(quinolin-7-yloxy)quinazoline (102 mg, 39%).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. stirringto stir at ambient temperature for a few minutes
  3. extractionThe reaction mixture was extracted 4 times with ethyl acetate
  4. washthe organic extracts washed with water and brine
  5. dry with materialThe organic extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed by evaporation
  8. customThe residue was triturated with ether/isohexane
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-38211a4e4b754ee4b088506079758e11
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07074800B1

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