반응 #1129341

반응 방정식

{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

azetidin-3-ol hydrochloride

→

title compound

수율 62.0%

1-({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}acetyl)azetidin-3-ol

수율 62.0%

용매

N,N-dimethylformamide

triethylamine

water

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   세척The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
3. 3
   건조dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   세척eluted with ethyl acetate-methanol (100/0 to 90/10, volume ratio)
7. 7
   기타to give colorless 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 (190 mg), 1H-1,2,3-benzotriazol-1-ol (70 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (100 mg), azetidin-3-ol hydrochloride (80 mg), triethylamine (80 mg) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 15 hr. 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, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and eluted with ethyl acetate-methanol (100/0 to 90/10, volume ratio) to give colorless crystals. The crystals were recrystallized from acetone-hexane to give the title compound (130 mg, yield 62%) as colorless prism crystals.

출처