p-Toluenesulfonic acid → 2-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

HRID 591809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591809
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[CH:5]=[C:4]([CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[C:13]=1[C:14]([NH2:16])=[O:15].S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:16][C:14](=[O:15])[C:13]3[C:12](=[CH:20][C:19]([F:21])=[CH:18][C:17]=3[F:22])[N:11]=2)[CH:5]=[C:4]([CH3:10])[N:3]=1

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 27630042,6-Dimethylpyridine-4-carbaldehydeHCID 23665763Sodium BisulfiteHCID 594419592-Amino-4,6-difluorobenzamide

Produkt 1

HCID 1363480062-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a solution of 2,6-dimethyl-pyridine-4-carbaldehyde (0.99 g, 7.32 mmol) and 2-amino-4,6-difluorobenzamide (1.26 g, 7.32 mmol) in N,N-dimethyl acetamide (20 mL) were added sodium hydrogen sulfite (58.5 wt %, 1.59 g, 8.78 mmol) and p-toluenesulfonic acid (0.21 g, 1.09 mmol). The reaction mixture was stirred at 115° C. for 16 hours under nitrogen. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water (50 mL) was added, the precipitated solid was filtered, washed with water, and dried under vacuum, to give 2-(2,6-dimethyl-pyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one as a yellow solid. Yield: 0.63 g (30%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater (50 mL) was added
  4. filtrationthe precipitated solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-97e022fe91304b03843517cb6ba437c0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238640B2

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