Reacción #356466

Ecuación de reacción

H2O

NH4OH

5-[7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridin-2-ylamine

acetic anhydride

HCl

→

title compound

Rendimiento 97.0%

N-{5-[7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridin-2-yl}-acetamide

Rendimiento 97.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCooled to 60° C.
2. 2
   Concentraciónconcentrated in vaccum to dryness (water bath temperature 60° C.)
3. 3
   Otrodried in HV
4. 4
   Otroto give
5. 5
   workup.ADDITIONan orange solid (2.465 g, 113%, mixture of mono- and diacetylated compound)
6. 6
   workup.STIRRINGstirred at 23° C. for 1.5 h
7. 7
   Otroresulting in a clear red solution
8. 8
   Filtraciónfiltered the precipitate off,
9. 9
   Lavadowashed with H2O
10. 10
    Otrodried in HV
11. 11
    Otrodrying in HV

Procedimiento

A mixture of 5-[7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-3-ylethynyl]-pyridin-2-ylamine (example 55) (2.00 g, 4.47 mmol) in acetic anhydride (15 mL) was stirred at 120° C. for 1 h. Cooled to 60° C., concentrated in vaccum to dryness (water bath temperature 60° C.) and dried in HV to give an orange solid (2.465 g, 113%, mixture of mono- and diacetylated compound). Suspended in THF (30 mL) at 23° C., added NH4OH (25%, 13.3M, 1.0 mL, 13.4 mmol) and stirred at 23° C. for 1.5 h resulting in a clear red solution, adjusted pH with 1N HCl until pH 1, added H2O (total volume 200 mL), filtered the precipitate off, washed with H2O and dried in HV, followed by trituration with ether and drying in HV to give the title compound as an orange solid (2.130 g, 97%). MS [ISN] 488.1[(M−H)−]; mp 266° C.

Fuente