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Triethylamine → 4-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

HRID 1619496
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1619496
P(Cl)(Cl)(Cl)=O.O1[C:10]2([CH2:15][CH2:14][CH:13]([O:16][C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][C:26]=3[O:27][CH3:28])[N:23]=[CH:22][NH:21][C:20]4=O)[CH2:12][CH2:11]2)[O:9]CC1.C(N(CC)CC)C.[Cl:37][C:38]1[C:39]([F:45])=[C:40]([CH:42]=[CH:43][CH:44]=1)[NH2:41]>C(#N)C>[Cl:37][C:38]1[C:39]([F:45])=[C:40]([NH:41][C:20]2[C:19]3[C:24](=[CH:25][C:26]([O:27][CH3:28])=[C:17]([O:16][CH:13]4[CH2:12][CH2:11][C:10](=[O:9])[CH2:15][CH2:14]4)[CH:18]=3)[N:23]=[CH:22][N:21]=2)[CH:42]=[CH:43][CH:44]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 24813Phosphorus oxychlorideHCID 750143-Chloro-2-fluoroaniline2×HCID 1359917776-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one

Produkt 1

HCID 581572644-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel3×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

3.25 ml phosphorus oxychloride are added dropwise to 6.50 g 6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one in 65 ml acetonitrile under an argon atmosphere. Then the reaction mixture is heated to 40° C., combined dropwise with 5.00 ml triethylamine and refluxed for 2 h. After cooling to ambient temperature 1.40 ml triethylamine and 2.60 ml 3-chloro-2-fluoro-aniline, dissolved in 5 ml acetonitrile, are added and the reaction mixture is stirred overnight at 40° C. Then a further 0.70 ml of 3-chloro-2-fluoro-aniline dissolved in 2 ml acetonitrile are added dropwise and the reaction mixture is stirred for a further 10 h. After cooling to ambient temperature the precipitate formed is suction filtered, taken up in 1 N hydrochloric acid, combined with 6 N isopropanolic hydrochloric acid and stirred at ambient temperature until the ketal cleaving is complete. The precipitate formed is suction filtered and combined with methylene chloride and 1 N sodium hydroxide solution. The aqueous phase is separated off and extracted with methylene chloride, the combined extracts are evaporated down and the flask residue is brought to crystallisation with diisopropylether.

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. additionare added
  3. additionare added dropwise
  4. stirringthe reaction mixture is stirred for a further 10 h
  5. temperatureAfter cooling to ambient temperature the precipitate
  6. customformed
  7. filtrationfiltered
  8. stirringstirred at ambient temperature until the ketal cleaving
  9. customThe precipitate formed
  10. filtrationfiltered
  11. customThe aqueous phase is separated off
  12. extractionextracted with methylene chloride
  13. customthe combined extracts are evaporated down
  14. customthe flask residue is brought to crystallisation with diisopropylether

Quellen und Nachweise

ORD-Eintrag
ord-7960bc97a79a4753bffce8151c22da2a
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772298B2

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