Potassium Carbonate → 7-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-4-(quinolin-7-yloxy)quinazoline

HRID 1791523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791523
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][S:21](=[O:25])(=[O: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:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][CH:39]=[N:40]2)=[CH:35][CH:34]=1.[OH-].[Na+]>CN(C=O)C>[O:24]=[S:21]1(=[O:25])[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([O:32][C:33]4[CH:42]=[C:41]5[C:36]([CH:37]=[CH:38][CH:39]=[N:40]5)=[CH:35][CH:34]=4)=[N:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])[CH2:19][CH2:20]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 219360004-Chloro-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazolineHCID 1354268667-Hydroxyquinoline

Produkt 1

HCID 98703767-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-4-(quinolin-7-yloxy)quinazolineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline (220 mg, 0.57 mmol), potassium carbonate (106 mg, 0.77 mmol) and 7-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodium hydroxide solution (40 ml) and stirred at ambient temperature for a few minutes. The crude solid was collected by filtration washing with water. The resultant solid was dissolved in dichloromethane (2 ml) and was filtered through phase separating paper. The filtrate was evaporated under vacuum to give a solid residue which was triturated with ether, filtered and dried to give 7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxy-4-(quinolin-7-yloxy)quinazoline (205 mg, 73%).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. stirringstirred at ambient temperature for a few minutes
  3. filtrationThe crude solid was collected by filtration
  4. washwashing with water
  5. dissolutionThe resultant solid was dissolved in dichloromethane (2 ml)
  6. filtrationwas filtered through phase
  7. customseparating paper
  8. customThe filtrate was evaporated under vacuum
  9. customto give a solid residue which
  10. customwas triturated with ether
  11. filtrationfiltered
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b95c0f24fb5144c7b69042eedf25564a
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074800B1

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