Acetic Anhydride → HCID 53753113, Verbindung

Anhydrous zinc chloride (0.106 g, 0.78 mmol) was fused with a nitrogen purge in a round bottom flask with an open flame. The reaction vessel was allowed to return to ambient temperature, at which time dioxane (6 mL) was then added. To this mixture was added 6-fluoro-3-(2-fluoro-phenyl)-2-methyl-3H-quinazolin-4-one (0.108 g, 0.39 mmol), acetic anhydride (0.111 mL, 1.18 mmol), and 2-dimethylaminomethylthiazole-4-carboxaldehyde (0.280 g, 1.18 mmol in 4 mL of dioxane). The reaction was refluxed for four days, at which time it was cooled to ambient temperature, and diluted with water. Sodium carbonate was added until the mixture was basic. The mixture was repeatedly extracted with chloroform. The chloroform extracts were combined to form a chloroform layer which was washed with aqueous bisulfite, water and brine and finally was dried over sodium sulfate and concentrated to yield a dark residue. This residue was triturated with ether. filtered and dried to afford 0.051 g (31%) of 2-[2-(2-dimethylaminomethyl-thiazol-4-yl)-vinyl]-6-fluoro-3-(2-fluoro-phenyl)-3H-quinazolin-4-one as tan solid.

1. custompurge in a round bottom flask with an open flame
2. customto return to ambient temperature, at which time dioxane (6 mL)
3. additionwas then added
4. temperatureThe reaction was refluxed for four days, at which time it
5. extractionThe mixture was repeatedly extracted with chloroform
6. customto form a chloroform layer which
7. washwas washed with aqueous bisulfite, water and brine
8. dry with materialfinally was dried over sodium sulfate
9. concentrationconcentrated
10. customto yield a dark residue
11. customThis residue was triturated with ether
12. filtrationfiltered
13. customdried

ORD-Eintrag

ord-ec78658da9584af198856fa90abaf8b0

Quelldatensatz

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06306864B1