تفاعل #2136109

معادلة التفاعل

4′-({4-[trans-4-(2-cyclopropyl-2-hydroxypropoxy)cyclohexyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

hydroxylammonium chloride

sodium hydrogen carbonate

dimethyl sulfoxide

→

title compound

المردود 53.5%

4-[trans-4-(2-cyclopropyl-2-hydroxypropoxy)cyclohexyl]-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propylpyrazolo[1,5-a]pyrimidin-5(4H)-one

المردود 53.5%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at 90° C. for 20 hr
2. 2
   غسيلwashed with water
3. 3
   تجفيفwith saturated brine, and dried over anhydrous magnesium sulfate
4. 4
   أخرىThe solvent was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONthe residue was dissolved in tetrahydrofuran (2 mL)
6. 6
   workup.ADDITIONN,N′-Carbonyldiimidazole (0.076 g) and then with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.070 mL) was added
7. 7
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hr
8. 8
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
9. 9
   غسيلwashed with 1 M hydrochloric acid
10. 10
    تجفيفwith saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate
11. 11
    أخرىThe solvent was evaporated under reduced pressure
12. 12
    أخرىthe residue was purified by silica gel column chromatography

الإجراء التجريبي

A mixture of hydroxylammonium chloride (0.33 g), sodium hydrogen carbonate (0.49 g) and dimethyl sulfoxide (2 mL) was stirred at 50° C. for 30 min, 4′-({4-[trans-4-(2-cyclopropyl-2-hydroxypropoxy)cyclohexyl]-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.22 g) was added, and the mixture was stirred at 90° C. for 20 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (2 mL). N,N′-Carbonyldiimidazole (0.076 g) and then with 1,8-diazabicyclo[5.4.0]undec-7-ene (0.070 mL) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid, then with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.13 g, 52%).

المصدر