1,8-Diazabicyclo(5.4.0)undec-7-ene → (+/-)-4-(4-Fluorophenyl)-5-(pyridin-4-yl)-1-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)imidazole

HRID 9874노트

반응식

HRID 9874 반응식
C1(C)C=CC(S([CH:10]([N+:18]#[C-:19])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)(=O)=O)=CC=1.[N:21]1[CH:26]=[CH:25][C:24]([CH:27]=[N:28][CH:29]2[CH2:37][CH:36]3[N:32]([CH2:33][CH2:34][CH2:35]3)[CH2:31][CH2:30]2)=[CH:23][CH:22]=1.C1CCN2C(=NCCC2)CC1>ClCCl>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[N:18]=[CH:19][N:28]([CH:29]3[CH2:37][CH:36]4[N:32]([CH2:33][CH2:34][CH2:35]4)[CH2:31][CH2:30]3)[C:27]=2[C:24]2[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=2)=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10827289a-Tosyl-(4-fluorobenzyl) isocyanideHCID 21988493(+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine

생성물 1

HCID 10133267(+/-)-4-(4-Fluorophenyl)-5-(pyridin-4-yl)-1-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)imidazole수율 14.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

α-(p-Toluenesulfonyl)-4-fluorobenzylisocyanide (10.1 g, 34.9 mmol) and (±)-7-(4-pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine (8.0 g (34.9 mmol), prepared as described in 2)) were dissolved in dichloromethane (150 ml). To the solution was added 1,8-diazabicyclo[5.4.0]-7-undecene (5.22 ml, 34.9 mmol), and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=20:1:1), to give the title compound (1.87 g) as a pale yellow powder (yield 14%).

후처리

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. additionTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionthis was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel (eluent, ethyl acetate:methanol:isopropylamine=20:1:1)

출처 및 근거

ORD 기록
ord-8666654f56c240ce8062fe43832322e8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091352B2

반응 노트

불러오는 중…