Chloroacetaldehyde → 3-[4-(Imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357017ノート

反応式

HRID 357017 の反応式
[NH2:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][S:15][C:14]2=[O:19])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:21][CH:22]=O>C(O)C>[N:1]1[CH:21]=[CH:22][N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[C:17](=[O:18])[CH2:16][S:15][C:14]3=[O:19])[C:2]=12

参加物

4

反応物 2

HCID 33ChloroacetaldehydeHCID 189367033-[4-(2-Aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione

生成物 1

HCID 189368403-[4-(Imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 14.08 g (50 mmol) of 3-[4-(2-aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione in 150 ml of ethanol, 50 ml of a 40% chloroacetaldehyde solution was added at 60° C., followed by refluxing for 2 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: n-hexane/residue=1/4) to yield 10.04 g (65.8%, light yellow crystal) of the desired product.

後処理

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent: n-hexane/residue=1/4)

出典と根拠

ORDレコード
ord-a61a0d71f33c4766b7fefdcddfe9be88
出典データセット
uspto-grants-1998_11
特許番号
US05840732

反応ノート

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