تفاعل #66368

معادلة التفاعل

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

المردود 77.4%

المذيبات

ethyl acetate

thionylchloride

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONThe solvent was distilled
2. 2
   أخرىevaporated to dryness
3. 3
   أخرىdried 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
   غسيلwashed with saturated aqueous NaHCO3 and brine
7. 7
   تجفيفThe organic layer was dried over Na2SO4
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5

الإجراء التجريبي

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%).

المصدر