Triethylamine → 4-Acetyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-1-naphthalenecarboxamide

Temperature

25 °C

A solution of 2-amino-N-(2,2,2-trifluoroethyl)acetamide (21.90 g, 0.14 mol) in 1,2-dichloroethane (80 mL) was added dropwise over 15 min to a solution of the product of Example 7, Step A (32.50 g, 0.14 mol) in 1,2-dichloroethane (160 mL) at a temperature of 25 to 30° C. The resulting mixture was further stirred for 10 min at 25° C. A solution of triethylamine (14.20 g, 0.14 mol) in 1,2-dichloroethane (80 mL) was then added dropwise over 44 min at 25° C., and the mixture was stirred further for 20 min at 25° C. The solvent was removed under reduced pressure, and the residue was dissolved in hot acetonitrile (50 mL). The mixture was then cooled to 25° C., and water (40 mL) was added dropwise. The mixture was further cooled to 0° C. and filtered. The isolated solid was washed with water (100 mL) and dried overnight in a vacuum oven (approximately 16-33 kPa at 50° C.) to provide the title product as an off-white solid (37 g, 75% yield) melting at 169-169° C.

1. stirringthe mixture was stirred further for 20 min at 25° C
2. customThe solvent was removed under reduced pressure
3. dissolutionthe residue was dissolved in hot acetonitrile (50 mL)
4. temperatureThe mixture was then cooled to 25° C.
5. additionwater (40 mL) was added dropwise
6. temperatureThe mixture was further cooled to 0° C.
7. filtrationfiltered
8. washThe isolated solid was washed with water (100 mL)
9. customdried overnight in a vacuum oven (approximately 16-33 kPa at 50° C.)

ORD record

ord-f1e41d41f8d643aea9a2e03aaa85f42a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546618B2