Potassium Carbonate → 6-Methoxy-4-(1-methylindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline

HRID 454287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454287
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][CH2:21][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:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH3:40])[CH:35]=[CH:34]2>CC(N(C)C)=O>[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][CH2:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH3:40])[CH:35]=[CH:34]2

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 108445251-Methyl-1H-indol-5-olHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline

Produkt 1

HCID 220308516-Methoxy-4-(1-methylindol-5-yloxy)-7-(3-piperidinopropoxy)quinazolineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Nitrogen was bubbled through a mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (335 mg, 0.68 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (281.5 mg, 2.04 mmol), 5-hydroxy-1-methylindole (100 mg, 0.68 mmol) and DMA (4.0 ml) for 5 minutes. The mixture was then stirred at 90° C. for 4 hours under an atmosphere of nitrogen and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated under vacuum. The residue was purified by trituration with methanol then water to give 6-methoxy-4-(1-methylindol-5-yloxy)-7-(3-piperidinopropoxy)quinazoline (148 mg, 49%).

Aufarbeitung

  1. custom(prepared
  2. customfor 5 minutes
  3. temperatureto cool to ambient temperature
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated under vacuum
  6. customThe residue was purified by trituration with methanol

Quellen und Nachweise

ORD-Eintrag
ord-900c423fb1af470b8e1b8e2a04a2d6b1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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