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2-Bromoethanol → N-[(4-chlorophenyl)methyl]-7-(2-hydroxyethyl)-2-(3-hydroxypropyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

HRID 2299299
ノート
印刷プレビュー

反応式

HRID 2299299 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:23])=[C:12]3[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][OH:22])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][CH2:34][OH:35].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][OH:22])[S:16][C:13]=3[N:14]([CH2:33][CH2:34][OH:35])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 108982-Bromoethanol3 回HCID 11430Potassium Carbonate2 回HCID 24758Sodium hydrideHCID 178522938HCID 178522938、化合物

生成物 1

HCID 6482397N-[(4-chlorophenyl)methyl]-7-(2-hydroxyethyl)-2-(3-hydroxypropyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide収率 39%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(3-hydroxypropyl)-thieno-[2,3-b]pyridine-5-carboxamide (Example No. 8) (0.330 g) in DMF (5 mL) are added K2CO3 (0.363 g) and 2-bromoethanol (0.19 mL). The reaction is heated to 100° C. and stirred for 18 h. An additional 0.19 mL of 2-bromoethanol is added and stirring is continued for 18 h. An additional 0.19 mL of 2-bromoethanol and 0.363 g of K2CO3 is added. After 5 h, 35 mg of NaH (60% oil dispersion) is added. The reaction is stirred for 1 h. The reaction mixture is cooled to rt and concentrated in vacuo. The residue is suspended in CH2Cl2 and H2O. The resulting off-white precipitate is filtered off and purified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.145 g (39%) of the title compound as a white solid.

後処理

  1. stirringstirring
  2. waitis continued for 18 h
  3. waitAfter 5 h
  4. stirringThe reaction is stirred for 1 h
  5. temperatureThe reaction mixture is cooled to rt
  6. concentrationconcentrated in vacuo
  7. filtrationThe resulting off-white precipitate is filtered off
  8. custompurified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-628a6efb5eb941bcac3ceade7282d9d9
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06495683B2

反応ノート

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