1-Bromo-3-chloropropane → 4-(4-Chloro-2-fluoroanilino)-7-(3-chloropropoxy)-6-methoxyquinazoline

HRID 2227937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2227937
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:22])[CH:3]=1.Br[CH2:24][CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:24][CH2:25][CH2:26][Cl:27])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:22])[CH:3]=1

Komponenten

6

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Produkt 1

HCID 109821564-(4-Chloro-2-fluoroanilino)-7-(3-chloropropoxy)-6-methoxyquinazolineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (957 mg, 3 mmol), (prepared as described for the starting material in Example 2), 1-bromo-3-chloropropane (2.36 g, 15 mmol) and potassium carbonate (2.1 g, 15 mmol) in DMF (20 ml) was heated at 40° C. for 1.5 hours. The mixture was allowed to cool, was diluted with water and extracted with ethyl acetate (3×50 ml). The organic extracts were combined, washed with water and brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was triturated with hexanelethyl acetate, collected by filtration and dried under vacuum to give 4-(4-chloro-2-fluoroaniiino)-7-(3-chloropropoxy)-6-methoxyquinazoline (650 mg, 55%).

Aufarbeitung

  1. custom(prepared
  2. temperatureto cool
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation
  7. customThe residue was triturated with hexanelethyl acetate
  8. filtrationcollected by filtration
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6f2f6bde4c4c40858a4f7fba95dcb3b6
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06414148B1

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