반응 #74649

반응 방정식

Ethyl acetate

Tert-butyl 3-[5-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-1-yl]azetidine-1-carboxylate

N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

potassium carbonate

→

title compound

Tert-butyl 3-{5-[5-chloro-2-(4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}-2,5-difluorophenoxy)phenyl]-1H-pyrazol-1-yl}azetidine-1-carboxylate

용매

water

dimethylsulphoxide

dichloromethane

tert-butylmethyl ether

반응 조건

후처리

1. 1
   workup.ADDITIONTo this slurry was added
2. 2
   기타the layers separated
3. 3
   세척The ethyl acetate was washed with water (2×800 mL)
4. 4
   건조saturated aqueous sodium chloride solution (200 mL) and then dried over anhydrous magnesium sulphate
5. 5
   workup.ADDITIONTo this suspension, tert-butylmethyl ether (250 mL) was added
6. 6
   세척the mixture was washed with dilute aqueous sodium chloride solution (1000 mL)
7. 7
   건조the organics were dried over magnesium sulphate
8. 8
   여과filtered
9. 9
   기타the solvents removed in-vacuo
10. 10
    기타to give a pale yellow solid
11. 11
    기타whilst evaporating the dichloromethane in vacuo
12. 12
    기타to give a white precipitate which
13. 13
    여과was filtered off
14. 14
    세척washed with a little tert-butylmethyl ether

실험 절차

Tert-butyl 3-[5-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (Preparation 851, 80.0 g, 0.2287 mol) and potassium carbonate (94.82 g, 0.686 mol) were combined in dimethylsulphoxide (600 mL). To this slurry was added N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide, (Preparation 647, 101.87 g, 0.2287 mol) and stirred at room temperature for 4.5 hours. Ethyl acetate (1600 mL) and water (1000 mL) were added and the layers separated. The ethyl acetate was washed with water (2×800 mL), then saturated aqueous sodium chloride solution (200 mL) and then dried over anhydrous magnesium sulphate. To this suspension, tert-butylmethyl ether (250 mL) was added and the mixture was washed with dilute aqueous sodium chloride solution (1000 mL), the organics were dried over magnesium sulphate, filtered and the solvents removed in-vacuo to give a pale yellow solid. This solid was dissolved in dichloromethane (500 mL) and tert-butylmethyl ether was added gradually whilst evaporating the dichloromethane in vacuo to give a white precipitate which was filtered off and washed with a little tert-butylmethyl ether to give the title compound as a white solid, (145.47 g).

출처