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Piperazine → ethyl 6,8-difluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

HRID 1085782
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HRID 1085782 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]1[CH:14]([CH3:16])[S:15][C:7]1=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22].C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[N:8]1[CH:14]([CH3:16])[S:15][C:7]1=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22]
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참가 물질

5

반응물 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 9973824ethyl 6,7,8-trifluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

생성물 1

HCID 10000764ethyl 6,8-difluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate수율 73.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
60 °C

실험 절차

Ethyl 6,7,8-trifluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate (0.33 g) and 0.14 g of potassium carbonate were suspended in 10 ml of N,N-dimethylformamide, 0.13 g of anhydrous piperazine was added and the mixture was stirred at 60° C. for 2 hours. N,N-Dimethylformamide was evaporated therefrom in vacuo, the residue was dissolved in chloroform, the solution was washed with water, dried over magnesium sulfate, the solvent was evaporated therefrom, the residue was subjected to a silica gel column chromatography (30 g of Wakogel C-300 being used) and eluted with chloroform-methanol (4:1) to give 0.29 g of the title product, m.p. 195°-198° C. (decompn).

후처리

  1. customN,N-Dimethylformamide was evaporated
  2. dissolutionin vacuo, the residue was dissolved in chloroform
  3. washthe solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washeluted with chloroform-methanol (4:1)

출처 및 근거

ORD 기록
ord-02a4579fc57b49e782eaf4c5f508d360
출처 데이터셋
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05011831

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