Methanol → 4-(4-Bromo-2-fluoroanilino)6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

HRID 2182550

Reaktionsgleichung

Reaktionsgleichung von HRID 2182550
O[O:2][S:3]([O-:5])=O.[K+].[Br:7][C:8]1[CH:32]=[CH:31][C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28]SC)=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:33])[CH:9]=1.[CH3:34]O>O.C(Cl)Cl>[Br:7][C:8]1[CH:32]=[CH:31][C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][CH2:28][S:3]([CH3:34])(=[O:5])=[O:2])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:33])[CH:9]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 224782814-(4-Bromo-2-fluoroanilino)-6-methoxy-7-(3-methylthiopropoxy)quinazolineHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 187534474-(4-Bromo-2-fluoroanilino)6-methoxy-7-(3-methylsulphonylpropoxy)quinazolineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of OXONE, (trade mark of E.I. du Pont de Nemours & Co., Inc), (800 mg) in water (4.5 ml) was added to a solution of 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3 methylthiopropoxy)quinazoline (300 mg, 0.66 mmol), (prepared as described in Example 31), in methanol (15 ml) and the mixture was stirred for 4 hours at ambient temperature. The mixture was diluted with methylene chloride, was washed with aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvent was removed by evaporation. The residue was triturated with ethyl acetate/hexane, collected by filtration and dried to give 4-(4-bromo-2-fluoroanilino)6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (235 mg, 73%).

Aufarbeitung

  1. washwas washed with aqueous sodium hydrogen carbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe residue was triturated with ethyl acetate/hexane
  5. filtrationcollected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ecc861c3dbb04a3baa0f9b9cf4f97a41
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897210B2

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