반응 #170215
ord-e804a1ab53e341f5bfef05a2426c4de4
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후처리
- 1기타then partitioned between ethyl acetate (20 mL) and water (30 mL)
- 2기타The aqueous layer was separated
- 3추출successively extracted with ethyl acetate (2×20 mL) and dichloromethane (2×20 mL)
- 4세척The combined organic phases were washed with a saturated solution of sodium chloride (3×30 mL)
- 5건조dried over sodium sulfate
- 6여과filtered
- 7농축concentrated to dryness
- 8기타The residue was purified by chromatography on silica gel
- 9기타The residue was triturated in pentane
실험 절차
3-(Thiophen-2-ylmethoxy)-azetidine hydrochloride (127 mg, 0.62 mmol), EDCI (120 mg, 0.62 mmol), HOBt (86 mg, 0.62 mmol) and diisopropylethylamine (180 μL, 1.03 mmol) were successively added to a solution of (E)-3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)acrylic acid hydrochloride (100 mg, 0.41 mmol) in dimethylformamide (10 mL) at room temperature. The reaction mixture was stirred overnight then partitioned between ethyl acetate (20 mL) and water (30 mL). The aqueous layer was separated and successively extracted with ethyl acetate (2×20 mL) and dichloromethane (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×30 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (98:2 to 93:7) as eluent. The residue was triturated in pentane to afford the title product as a pale orange solid (21 mg, 14%).