반응 #1129340

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′-ethylcarbodiimidehydrochloride

methylamine hydrochloride

sodium hydrogen carbonate

→

title compound

수율 53.7%

N-Methyl-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 53.7%

용매

N,N-dimethylformamide

triethylamine

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   세척The organic layer was washed with 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 95/5, 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 (200 mg), 1H-1,2,3-benzotriazol-1-ol (80 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimidehydrochloride (110 mg), methylamine hydrochloride (50 mg), triethylamine (85 mg) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 2.5 days. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with 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 95/5, volume ratio) to give colorless crystals. The crystals were recrystallized from acetone-hexane to give the title compound (110 mg, yield 52%) as colorless prism crystals.

출처