Tetrahydrofuran → (1-(2-(fur-2-ylmethoxy)ethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

HRID 582067ノート

反応式

HRID 582067 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][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].CS([CH2:41][CH2:42][O:43][CH2:44][C:45]1[O:46][CH:47]=[CH:48][CH:49]=1)(=O)=O>O>[O:46]1[CH:47]=[CH:48][CH:49]=[C:45]1[CH2:44][O:43][CH2:42][CH2:41][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

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 21223641Fur-2-ylmethyl 2-methanesulfonylethyl ether

生成物 1

HCID 53677515(1-(2-(fur-2-ylmethoxy)ethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-78 °C

実験手順

Combine (1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine (0.5 g, 1.6 mmol) and tetrahydrofuran (10 mL). Cool to -78° C. Add dropwise, a solution of potassium bis(trimethylsilyl)amide (3.6 mL, 0.5M in toluene, 1.8 mmol). After 30 minutes, add fur-2-ylmethyl 2-methanesulfonylethyl ether (1.8 mmol). Warm to ambient temperature and heat to reflux. After 18 hours, cool to ambient temperature and add water. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give (1-(2-(fur-2-ylmethoxy)ethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine: Rf =0.55 (2% triethylamine/10% methanol/ethyl acetate).

後処理

  1. additionAdd dropwise
  2. temperatureWarm to ambient temperature
  3. temperatureheat to reflux
  4. waitAfter 18 hours
  5. temperaturecool to ambient temperature
  6. customSeparate the organic layer
  7. extractionextract the aqueous layer with dichloromethane
  8. dry with materialDry the combined organic layers over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo

出典と根拠

ORDレコード
ord-d1ad043abaf94d33bf996d8fd1b7d3eb
出典データセット
uspto-grants-1999_07
特許番号
US05922737

反応ノート

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