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

HRID 323512
ノート
印刷プレビュー

反応式

HRID 323512 の反応式
[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+].[F:26][C:27]([F:38])([F:37])[O:28]OCCOS(C)(=O)=O.[I-].[Na+].[C:41](OCC)(=O)[CH3:42]>CN(C)C=O.C(OCC)(=O)C.CCCCCC.CCCCCC>[F:38][C:27]([F:26])([F:37])[O:28][CH2:41][CH2:42][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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 184645582-(Methanesulfonyloxy)ethyl trifluoromethoxy etherHCID 22036999tert-Butyl 4-((1H-benzo[d]imidazol-2-yl)amino)piperidine-1-carboxylate

生成物 1

HCID 22009444(1-(2-(trifluoromethoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒HCID 21226206Ethyl acetate hexane溶媒2 回

実験手順

Combine (1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine (0.158 g, 0.5 mmol) and dimethylformamide (4 mL). Cool in an ice-bath. Add sodium hydride (0.013 g, 60% in oil, 55 mmol). Warm to ambient temperature. After 30 minutes, add a solution of 2-(methanesulfonyloxy)ethyl trifluoromethoxy ether (0.15 g, 0.75 mmol) in dimethylformamide (1 mL). Add sodium iodide (0.11 g, 075 mmol). After 2 hours, heat to 80° C. After 4 hours, cool to ambient temperature. After 18 hours dilute the reaction mixture with ethyl acetate and extract with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with hexane, 30% ethyl acetate/hexane and then 50% ethyl acetate/hexane to give (1-(2-(trifluoromethoxy)ethyl)-1H-benzimidazol-2-yl)(1-(t-butoxycarbonyl)piperidin-4-yl)amine: Rf=0.26 (silica gel, 50% ethyl acetate/hexane).

後処理

  1. temperatureCool in an ice-bath
  2. waitAfter 2 hours
  3. temperatureheat to 80° C
  4. waitAfter 4 hours
  5. temperaturecool to ambient temperature
  6. extractionextract with brine
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

出典と根拠

ORDレコード
ord-ce25223739a24a39b52cba26dda738dd
出典データセット
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06211199B1

反応ノート

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