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Sodium hydride → (1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

HRID 323474
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HRID 323474 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[H-].[Na+].S(O[CH2:31][CH2:32][O:33][CH:34]([CH3:36])[CH3:35])(=O)(=O)C>CN(C)C=O>[CH:34]([O:33][CH2:32][CH2:31][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)([CH3:36])[CH3:35]
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 184650452-Isopropoxyethyl MethanesulfonateHCID 22036999tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate

생성물 1

HCID 22009477(1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Combine (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (2.76 g, 8.72 mmol), and sodium hydride (0.38 g, 9.5 mmol) in dimethylformamide (30 mL). After 30 minutes, add 2-(isopropoxy)ethyl mesylate (0.51 g, 5.5 mmol). Heat to 80° C. After 2.5 hours, cool the reaction mixture to ambient temperature and partition between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give (1-(2-(isopropoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine: Rf=0.73 (silica gel, dichloromethane/methanol/concentrated ammonium hydroxide, 90/10/0.1).

후처리

  1. waitAfter 2.5 hours
  2. temperaturecool the reaction mixture to ambient temperature
  3. custompartition between dichloromethane
  4. customSeparate the layers
  5. extractionextract the organic layer with water
  6. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-f9eb27cac30d489b8aaebfd70ba6de90
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211199B1

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