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Triphenylphosphine → 4-(4-Chloro-2-fluoroanilino)6-methoxy-7-(2-(3-oxomorpholino)ethoxy)quinazoline hydrochloride

HRID 547212
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 547212
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([OH:31])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][O:60][CH2:59][C:58]1=[O:63]>C(Cl)Cl.C1COCC1>[ClH:13].[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH2:55][CH2:56][N:57]4[CH2:62][CH2:61][O:60][CH2:59][C:58]4=[O:63])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1
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Komponenten

7

Edukt 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 152874004-(2-Hydroxyethyl)morpholin-3-one2×HCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Produkt 1

HCID 187534774-(4-Chloro-2-fluoroanilino)6-methoxy-7-(2-(3-oxomorpholino)ethoxy)quinazoline hydrochloride
Ausbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (400 mg, 2.3 mmol) was added dropwise to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (250 mg, 0.78 mmol), (prepared as described for the starting material in Example 2), triphenylphosphine (615 mg, 2.3 mmol) and 4-(2-hydroxyethyl)-3-morpholinone (170 mg, 1.17 mmol), (EP 580402A2), in methylene chloride (5 ml) under nitrogen. The mixture was stirred for 4 hours at ambient temperature, methylene chloride (5 ml) was added and stirring was continued for a further 18 hours at ambient temperature. THF (5 ml). 4-(2-hydroxyethyl)-3-morpholinone (113 mg, 0.78 mmol). triphenylphosphine (204 mg, 0.78 mmol) were added and diethyl azodicarboxylate (136 mg, 0.78 mmol) was then added dropwise. The mixture was stirred for 5 minutes at ambient temperature, and was purified by pouring directly onto a silica column, eluting with methylene chloride/ethyl acetate/methanol (5/4/1). The purified solid was dissolved in methylene chloride and 2M methanolic hydrogen chloride (0.5 ml) was added. The mixture was concentrated by evaporation and then diluted with ether. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(3-oxomorpholino)ethoxy)quinazoline hydrochloride (150 mg, 39%).

Aufarbeitung

  1. custom(prepared
  2. stirringstirring
  3. waitwas continued for a further 18 hours at ambient temperature
  4. stirringThe mixture was stirred for 5 minutes at ambient temperature
  5. customwas purified
  6. additionby pouring directly onto a silica column
  7. washeluting with methylene chloride/ethyl acetate/methanol (5/4/1)
  8. dissolutionThe purified solid was dissolved in methylene chloride
  9. addition2M methanolic hydrogen chloride (0.5 ml) was added
  10. concentrationThe mixture was concentrated by evaporation
  11. additiondiluted with ether
  12. filtrationThe resulting precipitate was collected by filtration
  13. washwashed with ether
  14. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b365bb33fed046b29e4ffb3582cf0fd6
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE042353E1

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