Triethylamine → HCID 24700958, compound

Temperature

0 °C

Triethylamine (1.03 ml, 7.4 mmol) and isobutyl chloroformate (0.76 ml, 5.5 mmol) were added to an acetonitrile solution (12 ml) of 6-chloronicotinic acid (0.58 g, 3.6 mmol) under ice cooling and the mixture was stirred at 0° C. for 30 minutes. To the solution mixture, 2,2,2-trifluoroethyl amine (0.88 ml, 11.2 mmol) was added and the mixture was stirred at room temperature for 10 minutes. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1). The purified product was concentrated under reduced pressure and diisopropyl ether and n-hexane were added. The insoluble matter precipitated was obtained by filtration and dried to obtain 6-chloro-N-(2,2,2-trifluoroethyl)nicotine amide (0.58 g) as light yellow powder.

1. stirringthe mixture was stirred at room temperature for 10 minutes
2. extractionwas then extracted with ethyl acetate
3. dry with materialThe extraction solution with ethyl acetate was dried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1)
6. concentrationThe purified product was concentrated under reduced pressure and diisopropyl ether and n-hexane
7. additionwere added
8. customThe insoluble matter precipitated
9. customwas obtained by filtration
10. customdried

ORD record

ord-3ac5f1f36c29460d9a037daac2348571

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598162B2