반응 #1129339

반응 방정식

ammonia

{2-[5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid

1H-1,2,3-benzotriazol-1-ol

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride

→

title compound

수율 62.0%

2-{2-[5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetamide

수율 62.0%

용매

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   온도cooled to 0° C
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 2.5 days
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
5. 5
   건조dried over magnesium sulfate
6. 6
   세척subjected to silica gel short column chromatography (eluted with ethyl acetate-methanol (95/5, volume ratio))
7. 7
   기타to give pale-yellow crystals
8. 8
   기타The crystals were recrystallized from acetone-hexane

실험 절차

A mixture of {2-[5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (210 mg), 1H-1,2,3-benzotriazol-1-ol (80 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (120 mg) and N,N-dimethylformamide (5 mL) was stirred at 50° C. for 30 min and cooled to 0° C. 10% Aqueous ammonia (1 mL) was added to the mixture, and the mixture was stirred at room temperature for 2.5 days. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and subjected to silica gel short column chromatography (eluted with ethyl acetate-methanol (95/5, volume ratio)) to give pale-yellow crystals. The crystals were recrystallized from acetone-hexane to give the title compound (130 mg, yield 62%) as pale-yellow prism crystals.

출처