Reacción #66368

Ecuación de reacción

3-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzoic acid hydrochloride

4-tert-butylaniline

→

N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamide

Rendimiento 77.4%

Disolventes

ethyl acetate

thionylchloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThe solvent was distilled
2. 2
   Otroevaporated to dryness
3. 3
   Otrodried under high vacuum for 1 h
4. 4
   workup.DISSOLUTIONThe acid chloride was then dissolved in dry pyridine (1 mL) under nitrogen
5. 5
   workup.STIRRINGThe mixture was stirred at room temperature for 1 h
6. 6
   Lavadowashed with saturated aqueous NaHCO3 and brine
7. 7
   SecadoThe organic layer was dried over Na2SO4
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5

Procedimiento

3-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzoic acid hydrochloride (45 mg, 0.125 mmol) was dissolved in thionylchloride (1 mL) and stirred at 60° C. for 1 hour. The solvent was distilled and the residue was taken up with toluene, evaporated to dryness and dried under high vacuum for 1 h. The acid chloride was then dissolved in dry pyridine (1 mL) under nitrogen and 4-tert-butylaniline (0.030 mL, 0.187 mmol, 1.5 eq) was added. The mixture was stirred at room temperature for 1 h and then diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5 to give 44 mg of N-(4-tert-butyl-phenyl)-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-benzamide as a white solid (77%).

Fuente