반응 #1276201

반응 방정식

ammonium hydroxide

{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

→

title compound

수율 39.2%

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 39.2%

용매

N,N-dimethylformamide

Water

반응 조건

후처리

1. 1
   온도cooled to 0° C
2. 2
   workup.STIRRINGThe whole was stirred at room temperature for 15 h
3. 3
   추출the resultant was extracted with ethyl acetate
4. 4
   세척The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio)
9. 9
   기타to give pale yellow crystals
10. 10
    기타The crystals were recrystallized from acetone-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 (230 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 mg), 1-hydroxybenzotriazole (100 mg) and N,N-dimethylformamide (5 mL) was stirred at 50° C. for 30 min, and then cooled to 0° C. To the mixture was added aqueous ammonium hydroxide solution (10%, 1 mL). The whole was stirred at room temperature for 15 h. Water was added to the residue 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 90:10, volume ratio) to give pale yellow crystals. The crystals were recrystallized from acetone-hexane to give the title compound (90 mg, 39%) as pale yellow prisms. MS 489 (MH+). mp 212-213° C.

출처