Phenacyl bromide → 3-[4-(2-Phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357026노트

반응식

HRID 357026 반응식
[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.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O>C(O)C>[C:24]1([C:22]2[N:1]=[C:2]3[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]4[C:17](=[O:18])[CH2:16][S:15][C:14]4=[O:19])=[CH:6][CH:5]=[CH:4][N:3]3[CH:21]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

4

반응물 2

HCID 6259Phenacyl bromideHCID 189367033-[4-(2-Aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione

생성물 1

HCID 189368343-[4-(2-Phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 5.69 g (20 mmol) of 3-[4-(2-aminopyridin-3-yloxy)butyl]thiazolidine-2,4-dione in 40 ml of ethanol, 3.98 g (20 mmol) of bromoacetophenone was added at room temperature, followed by refluxing for 1.5 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, 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/ethyl acetate=1/4) to yield 5.24 g (68.7%, light orange crystal) of the desired product.

후처리

  1. temperatureby refluxing for 1.5 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  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/ethyl acetate=1/4)

출처 및 근거

ORD 기록
ord-1c189bca81e24e9a9ce5011aed1bb25c
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840732

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