Water → 4-(Indol-6-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

HRID 1791630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791630
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[CH:28][NH:29]2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[NH:29]1[C:30]2[C:26](=[CH:25][CH:24]=[C:23]([O:22][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:31]=2)[CH:27]=[CH:28]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5245086-HydroxyindoleHCID 218748234-Chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

Produkt 1

HCID 220308634-(Indol-6-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazolineAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 4-chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (200 mg, 0.6 mmol), (prepared as described for the starting material in Example 50), and 6hydroxyindole (97 mg, 0.73 mmol) in DMF (3 ml) containing potassium carbonate (125 mg, 0.91 mmol) was heated at 90° C. for 2.5 hours. After cooling, water was added. The precipitate was filtered, washed with water and dried under vacuum. The residue was triturated with ether, filtered, washed with ether and dried under vacuum to give 4-(indol-6-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (130 mg, 50%).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. customThe residue was triturated with ether
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-468fcbe5be244819a8c75295abe707e7
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074800B1

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