Piperidine → 5-[3-(4-Fluorophenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357207노트

반응식

HRID 357207 반응식
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]=O)=[CH:25][CH:24]=1.N1CCCCC1>C(O)C>[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]=[C:18]2[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:9]3[N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=3)[C:19]2=[O:20])=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 101977823-(4-Fluorophenyl)propanalHCID 189366943-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

생성물 1

HCID 572946405-[3-(4-Fluorophenyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 964 mg (3.0 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 609 mg (4.0 mmol) of 3-(4-fluorophenyl)-1-propanal in 20 ml of ethanol, 26 mg (0.3 mmol) of piperidine was added, followed by refluxing for 4.5 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with purified water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=50/1) to yield 0.88 g (64.2%, yellow oily substance) of the desired product.

후처리

  1. temperatureby refluxing for 4.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with purified water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, chloroform/methanol=50/1)

출처 및 근거

ORD 기록
ord-abb9feedb09547a3bf0f53196d1fef8b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840732

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