1,1'-Carbonyldiimidazole → 3-Benzyloxy-1-(2,4-difluorophenyl)-6,7-difluoro-1H-quinazoline-2,4-dione

HRID 2270254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2270254
[CH2:1]([O:8][NH:9][C:10](=[O:28])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30]>C1COCC1>[CH2:1]([O:8][N:9]1[C:10](=[O:28])[C:11]2[C:12](=[CH:13][C:14]([F:18])=[C:15]([F:17])[CH:16]=2)[N:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C:29]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22632987N-Benzyloxy-2-(2,4-difluoroanilino)-4,5-difluoro-benzamide

Produkt 1

HCID 226329863-Benzyloxy-1-(2,4-difluorophenyl)-6,7-difluoro-1H-quinazoline-2,4-dioneAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-benzyloxy-2-(2,4-difluoroanilino)-4,5-difluoro-benzamide (Example I-4, 5.66 g, 15 mmol) and carbonyldiimidazole (2.83 g, 17 mmol) were combined in 300 mL of THF and heated to reflux for 30 hours. The solution was cooled, concentrated, and redissolved in chloroform. The solution was washed with 1N HCl, saturated NaHCO3, brine, and dried over magnesium sulfate. The solution was concentrated to give 4.25 g of a solid which was purified by column chromatography (silica gel, CHCl3/MeOH, 98:2) to give 2.0 g of the title compound as a solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 30 hours
  3. temperatureThe solution was cooled
  4. concentrationconcentrated
  5. dissolutionredissolved in chloroform
  6. washThe solution was washed with 1N HCl, saturated NaHCO3, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0297fa37487740ae9ce2aef095fc373f
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331538B1

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