Dimethylformamide → (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

HRID 323509

반응식

HRID 323509 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][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.CN(C)C=O.[H-].[Na+].[Si:29]([O:36][CH2:37][CH2:38]I)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>CO.ClCCl.ClCCl.O1CCCC1>[Si:29]([O:36][CH2:37][CH2:38][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][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilane

생성물 1

HCID 22009292(1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 21226129Dichloromethane methanol용매

실험 절차

Combine (1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (4.00 g, 13.87 mmol) and dimethylformamide (12 mL) and tetrahydrofuran (60 mL). Cool in an ice-bath. Add sodium hydride (24 mg, 15.3 mmol). After 24 hours, add 2-(t-butyldimethylsilyloxy) ethyl iodide (3.97 g, 13.87 mmol). After 60 hours, add ice to quench the reaction. Evaporate the quenched reaction mixture in vacuo to remove most of the tetrahydrofuran. Partition the evaporated reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer three times with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with dichloromethane and then 5% methanol/dichloromethane to give (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine: Rf=0.14 (silica gel, 40% ethyl acetate/dichloromethane).

후처리

  1. temperatureCool in an ice-bath
  2. waitAfter 60 hours
  3. additionadd ice
  4. customto quench
  5. customthe reaction
  6. customEvaporate
  7. customthe quenched reaction mixture in vacuo
  8. customto remove most of the tetrahydrofuran
  9. customPartition
  10. customthe evaporated reaction mixture between water and ethyl acetate
  11. customSeparate the layers
  12. extractionextract the organic layer three times with water
  13. dry with materialDry the organic layer over MgSO4
  14. filtrationfilter
  15. customevaporate in vacuo
  16. customto give a residue

출처 및 근거

ORD 기록
ord-e125e3d17ab74f5eac4e714d3a6ea61f
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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