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Potassium Carbonate → HCID 53869717, Verbindung

HRID 1421066
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1421066
[OH:1][CH:2]=[CH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[Cl:15][C:16]1[CH:35]=[CH:34][C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27](O)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[C:18]([F:36])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CN(C=O)C>[Cl:15][C:16]1[CH:35]=[CH:34][C:19]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:1][CH2:2][CH:3]=[CH:4][C:5]4[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=4)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[C:18]([F:36])[CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 67726470HCID 67726470, VerbindungHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Produkt 1

HCID 53869717HCID 53869717, VerbindungAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140
Toluene
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-hydroxyprop-2-en-1-yl)pyridine (180 mg, 1.3 mmol) and thionyl chloride (0.3 ml) in toluene (10 ml) was stirred at room temperature for 2 hours. The volatiles were removed by evaporation to give crude 4-(3-chloroprop-2-en-1-yl)pyridine hydrochloride (180 mg, 0.94 mmol)) This product was added to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (500 mg, 1.6 mmol) and potassium carbonate (500 mg, 4.9 mmol) in DMF (20 ml) and the mixture stirred at 100° C. for 1 hour. The reaction mixture was allowed to cool and partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (100/0 increasing to 95/5) and then by reverse phase (C18) HPLC eluting with methanol/water (30/70 increasing to 50/50) to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-(pyrid-4-yl)prop-2-en-1-yloxy)quinazoline (15 mg, 4%).

Aufarbeitung

  1. customThe volatiles were removed by evaporation
  2. customto give crude 4-(3-chloroprop-2-en-1-yl)pyridine hydrochloride (180 mg, 0.94 mmol)) This product
  3. stirringthe mixture stirred at 100° C. for 1 hour
  4. temperatureto cool
  5. custompartitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed by evaporation
  10. customThe residue was purified by column chromatography
  11. washeluting with methylene chloride/methanol (100/0 increasing to 95/5)
  12. washby reverse phase (C18) HPLC eluting with methanol/water (30/70 increasing to 50/50)

Quellen und Nachweise

ORD-Eintrag
ord-258fe62207dc41b99b2e6665da29dee9
Quelldatensatz
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06071921

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