반응 #66368

반응 방정식

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

수율 77.4%

용매

ethyl acetate

thionylchloride

반응 조건

후처리

1. 1
   workup.DISTILLATIONThe solvent was distilled
2. 2
   기타evaporated to dryness
3. 3
   기타dried 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
   세척washed with saturated aqueous NaHCO3 and brine
7. 7
   건조The organic layer was dried over Na2SO4
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The crude product was purified by chromatography on silica gel (eluant DCM/EtOH 95:5

실험 절차

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%).

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