ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Imidazole → 5-[2-(-1H-imidazol-1-yl)pyrid-5-yl]-1-azabicyclo[3.2.1]oct-3-ene

HRID 44457
ノート
印刷プレビュー

反応式

HRID 44457 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]23[CH2:22][N:19]([CH2:20][CH2:21]2)[CH2:18][CH:17]=[CH:16]3)=[CH:11][N:10]=1>CN(C)C=O>[N:1]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]34[CH2:22][N:19]([CH2:20][CH2:21]3)[CH2:18][CH:17]=[CH:16]4)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 102860575-(2-Bromopyrid-5-yl)-1-azabicyclo[3.2.1]oct-3-ene

生成物 1

HCID 670500635-[2-(-1H-imidazol-1-yl)pyrid-5-yl]-1-azabicyclo[3.2.1]oct-3-ene収率 49.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

0.64 g (9.42 mmol) of imidazole dissolved in 3 ml of dimethylformamide is introduced into a 10 ml three-necked round-bottomed flask. 0.415 g (10.4 mmol) of sodium hydride as a 60% dispersion in oil is then added and the mixture is stirred at room temperature for 1 hour. The mixture is then added to a solution of 5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]oct-3-ene (WO 03/057 697) (0.5 g, 1.89 mmol) in dimethylformamide and the reaction medium is heated at 85° C. for 15 hours and then at 110° C. for 24 hours and the solvent is evaporated off under reduced pressure. The residue is taken up in 10 ml of chloroform and 10 ml of saturated aqueous sodium carbonate solution. The aqueous phase is extracted again with 10 ml of chloroform and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions. 0.235 g of 5-[2-(−1H-imidazol-1-yl)pyrid-5-yl]-1-azabicyclo[3.2.1]oct-3-ene is obtained and is dissolved in 3 ml of isopropyl alcohol to add 0.327 ml of a 5.7N solution of hydrobromic acid in acetic acid. The crystals formed are collected by filtration and dried under vacuum.

後処理

  1. additionis introduced into a 10 ml three-necked round-bottomed flask
  2. temperaturethe reaction medium is heated at 85° C. for 15 hours
  3. waitat 110° C. for 24 hours
  4. customthe solvent is evaporated off under reduced pressure
  5. extractionThe aqueous phase is extracted again with 10 ml of chloroform
  6. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by chromatography on a column of silica gel
  11. washeluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions

出典と根拠

ORDレコード
ord-eedb6fcfb6f64249a71869e78f468f2e
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08541440B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート