반응 #170232

반응 방정식

3-((4-Chlorothiophen-2-yl)methoxy)-azetidine hydrochloride

EDCI

HOBt

diisopropylethylamine

(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride

→

title compound

수율 23.5%

(E)-6-(3-(3-((4-Chlorothiophen-2-yl)methoxy)azetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

수율 23.5%

용매

water

ethyl acetate

dimethylformamide

반응 조건

후처리

1. 1
   추출The aqueous phase was extracted with ethyl acetate (2×40 mL)
2. 2
   세척The combined organic phases were washed with a saturated solution of sodium chloride (3×40 mL)
3. 3
   건조dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated to dryness
6. 6
   기타The residue was triturated in diethyl ether

실험 절차

3-((4-Chlorothiophen-2-yl)methoxy)-azetidine hydrochloride (141 mg, 0.59 mmol), EDCI (113 mg, 0.59 mmol), HOBt (82 mg, 0.59 mmol) and diisopropylethylamine (171 μL, 1.00 mmol) were successively added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride (100 mg, 0.39 mmol) in dimethylformamide (6 mL) at room temperature. The reaction mixture was stirred overnight and then diluted by addition of ethyl acetate (40 mL) and water (40 mL). The aqueous phase was extracted with ethyl acetate (2×40 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was triturated in diethyl ether to afford the title compound as a pale yellow solid (37 mg, 23%).

출처