반응 #1276202

반응 방정식

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

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

1-hydroxybenzotriazole

methylamine hydrochloride

→

title compound

수율 58.4%

N-Methyl-2-{2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetamide

수율 58.4%

용매

N,N-dimethylformamide

triethylamine

Water

반응 조건

후처리

1. 1
   추출the resultant was extracted with ethyl acetate
2. 2
   세척The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 95:5, volume ratio)
7. 7
   기타to give colorless crystals
8. 8
   기타The crystals were recrystallized from ethyl acetate-hexane

실험 절차

A mixture of {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (200 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (120 mg), 1-hydroxybenzotriazole (80 mg), methylamine hydrochloride (60 mg), triethylamine (70 mg) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 15 h. Water was added to the mixture and the resultant was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 95:5, volume ratio) to give colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (120 mg, 57%) as colorless prisms. MS 503 (MH+). mp 190-192° C.

출처