HCID 178494219, Verbindung → Quinazoline hydrochloride

HRID 2182572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182572
BrCCOCCO[C:8]1[CH:17]=[C:16]2[C:11]([C:12](N([Cl:28])C3C=CC=CC=3F)(OC)[NH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1>CN1CCNCC1>[ClH:28].[N:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][CH:17]=2)[CH:12]=[N:13][CH:14]=1

Komponenten

3

Edukt 1

HCID 178494219HCID 178494219, Verbindung

Produkt 1

HCID 21186983Quinazoline hydrochlorideAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 531671-MethylpiperazineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 7-(2-(2-bromoethoxy)ethoxy)4-(chloro-2-fluoroanilino)4 methoxyquinazoline (150 mg, 0.32 mmol) in 1-methylpiperazine (2 ml) was heated at 100° C. for 1 hour. The mixture was allowed to cool and was partitioned between ethyl acetate and water. The organic layer was separated and washed with water and then brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica eluting with methylene chloride/methanol (85/15 followed by 80/20). The purified solid product was dissolved in methylene chloride/methanol (III) and 2.9M ethereal hydrogen chloride was added. The volatiles were removed by evaporation and the solid was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)+methoxy-722-[4-methylpiperazin-1-yl]ethoxy)ethoxy)quinazoline hydrochloride (54 mg, 28%).

Aufarbeitung

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography on silica eluting with methylene chloride/methanol (85/15 followed by 80/20)
  8. dissolutionThe purified solid product was dissolved in methylene chloride/methanol (III)
  9. addition2.9M ethereal hydrogen chloride was added
  10. customThe volatiles were removed by evaporation
  11. customthe solid was triturated with ether
  12. filtrationcollected by filtration
  13. washwashed with ether
  14. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1b26064afb2c4344b6cf5fc199fbbe0c
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897210B2

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