반응 #69554

반응 방정식

tetrahydrofuran

N-{3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}-1-hydroxycyclopropanecarboxamide

diborane

hydrochloric acid

→

title compound

수율 60.2%

1-[({3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}amino)methyl]cyclopropanol

수율 60.2%

용매

Water

n-heptane ethyl acetate

반응 조건

후처리

1. 1
   기타to be room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at 50° C. for one hour
3. 3
   추출the reaction mixture was extracted with ethyl acetate
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과The mixture was filtered
6. 6
   workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
7. 7
   기타The residue was purified by silica gel column (NI-1) chromatography (a mixed solvent of n-heptane and ethyl acetate

실험 절차

To a tetrahydrofuran (4 mL) solution of N-{3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}-1-hydroxycyclopropanecarboxamide (162 mg, 0.374 mmol) was added 0.99 M diborane (0.944 mL, 0.935 mmol), and the mixture was stirred at 55° C. for two hours. The temperature was made to be room temperature, and a 2N aqueous solution of hydrochloric acid (0.374 mL, 0.748 mmol) was added, and the mixture was stirred at 50° C. for one hour. Water was added to the reaction mixture at room temperature, and the reaction mixture was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column (NI-1) chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/1) to obtain the title compound (94.5 mg, 0.225 mmol).

출처