3-Morpholino-1-propanol → 4-[(3,4-Dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]-6-nitroquinazoline

HRID 346417

Reaktionsgleichung

Reaktionsgleichung von HRID 346417
[Na].[N:2]1([CH2:8][CH2:9][CH2:10][OH:11])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Cl:12][C:13]1[CH:14]=[C:15]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28](F)=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[C:16]([F:20])=[CH:17][C:18]=1[Cl:19]>C1COCC1>[Cl:12][C:13]1[CH:14]=[C:15]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:11][CH2:10][CH2:9][CH2:8][N:2]4[CH2:7][CH2:6][O:5][CH2:4][CH2:3]4)=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[C:16]([F:20])=[CH:17][C:18]=1[Cl:19]

Komponenten

5

Edukt 3

HCID 1995763-Morpholino-1-propanolHCID 5360545SodiumHCID 111761854-[(3,4-Dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline

Produkt 1

HCID 210800014-[(3,4-Dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]-6-nitroquinazolineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Sodium metal (5 equivalents) was added, under nitrogen atmosphere, to a solution of 3-(4-morpholinyl)-1-propanol (4 equivalents) in THF. The obtained suspension was stirred at 20° C. for two hours and was thereafter cannulated, under nitrogen atmosphere, into a solution of 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline. The reaction mixture was refluxed for 18 hours, the solvent was thereafter partially removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. Drying the combined organic extracts, evaporation and silica gel chromatography (using a mixture of 20% MeOH/30% CH2Cl2/50% EtOAc as elute) gave 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]-6-nitroquinazoline in 72% yield.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customthe solvent was thereafter partially removed under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. customDrying
  6. customthe combined organic extracts, evaporation and silica gel chromatography (
  7. additiona mixture of 20% MeOH/30% CH2Cl2/50% EtOAc
  8. washas elute)

Quellen und Nachweise

ORD-Eintrag
ord-44f5507bc07f4cd99812ba644cbcabc3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07172749B2

Verknüpfte Notizen

Wird geladen…