Hydrochloric Acid → 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one

HRID 454167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454167
ClC1C=CC([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]4)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=C(F)C=1.Cl.C(=O)([O-])O.[Na+]>>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)[N:10]=[CH:9][NH:8][C:7]2=[O:6]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 218748154-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

Produkt 1

HCID 1354581696-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-oneAusbeute 96,7 %

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

4-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (2.6 g, 5.6 mmol) was treated with 2.0 N aqueous hydrochloric acid (45 ml) and the mixture stirred at 95° C. for 2 hours. The mixture was cooled, basified by the addition of solid sodium hydrogen carbonate and the water removed by azeotroping with toluene. The residue was purified by silica column chromatography eluting with dichloromethane/methanol/0.880 aqueous ammonia (50/8/1) to give 6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one (1.8 g, 96%).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customthe water removed
  3. customby azeotroping with toluene
  4. customThe residue was purified by silica column chromatography
  5. washeluting with dichloromethane/methanol/0.880 aqueous ammonia (50/8/1)

Quellen und Nachweise

ORD-Eintrag
ord-603bfa2795da4a94a25dee47af526d1d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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