Reacción #68992

Ecuación de reacción

(5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone

N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-prop-2-ynyl-methanesulfonamide

ethyl acetate

→

N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-prop-2-ynyl-methanesulfonamide

Rendimiento 61.3%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 2 hours
2. 2
   Otrothe solvent was removed by reduced pressure distillation
3. 3
   workup.ADDITIONTo the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution
4. 4
   OtroThe two layers were separated
5. 5
   Lavadothe aqueous layer was washed with 10 ml of dichloromethane
6. 6
   LavadoThe organic layers were washed with 10 ml of water
7. 7
   Secadodried over magnesium sulfate
8. 8
   OtroThe dichloromethane layer was evaporated to dryness
9. 9
   Otroto yield an oil which

Procedimiento

A mixture of 0.108 g (0.56 mmol) of (5-amino-1H-pyrazol-4-yl)-thiophene-2-yl-methanone and 0.198 g (0.61 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-prop-2-ynyl-methanesulfonamide in 10 ml of glacial acetic acid was refluxed for 2 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 ml of dichloromethane and 10 ml of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 156 mg of N-{2-fluoro-5-[3-(thiophene-2-carbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-prop-2-ynyl-methanesulfonamide as a solid (yield 61%).

Fuente