Triethylamine → HCID 86603473, Verbindung

Temperatur

65 °C

To a solution of methyl 3-(benzoyloxy)-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate in anhydrous DMF were added O,N-dimethylhydroxylamine hydrochloride (2.5 eq.) and DIPEA (2.2 eq.). The mixture was stirred and warmed to 65° C. for 6 h. The mixture was cooled to room temperature and the solvent was removed under high vacuum. The residue was dissolved in methanol and p-fluoro-benzylamine (2.2 eq.) and triethylamine (2 eq.) were added. The mixture was stirred at 65° C. for 16 h. After cooling to room temperature the mixture was partitioned between aq. ammonium chloride and dichloromethane. The aq. phase was again extracted with dichloromethane. The combined organic phases were then extracted with 0.1 M NaOH. The aq. phase was then acidified to pH 5 ca. with 1 M aq. HCl and extracted with dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated to dryness. The crude product so obtained was used in the subsequent step without further purification.

1. temperatureThe mixture was cooled to room temperature
2. customthe solvent was removed under high vacuum
3. dissolutionThe residue was dissolved in methanol
4. stirringThe mixture was stirred at 65° C. for 16 h
5. temperatureAfter cooling to room temperature the mixture
6. customwas partitioned between aq. ammonium chloride and dichloromethane
7. extractionThe aq. phase was again extracted with dichloromethane
8. extractionThe combined organic phases were then extracted with 0.1 M NaOH
9. extractionextracted with dichloromethane
10. dry with materialThe organic phase was dried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated to dryness

ORD-Eintrag

ord-02f7382e83af45f6b87361f3389d21c7

Quelldatensatz

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07414045B2