Dimethyl Sulfoxide → Ethyl 2-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]cyclopropanecarboxylate

HRID 1094210노트

반응식

HRID 1094210 반응식
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)(C)=O.[CH:13]1([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24](=[O:42])[C:25](/[CH:35]=[CH:36]/[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:26][N:27]3[CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:22][C:21]=2[F:43])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O>[CH:13]1([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24](=[O:42])[C:25]([CH:35]4[CH2:8][CH:36]4[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:26][N:27]3[CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:22][C:21]=2[F:43])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66636880ethyl (2E)-3-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]acrylate

생성물 1

HCID 66636987Ethyl 2-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]cyclopropanecarboxylate수율 22%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 6 ml DMSO suspension of 200 mg of 60% sodium hydride was added 1.1 g of trimethylsulfoxonium iodide, followed by stirring for 30 minutes. To the reaction mixture was added 242 mg of ethyl (2E)-3-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]acrylate, followed by stirring at room temperature for 1 hour and at 60° C. for 1 hour. To the reaction mixture was added water, followed by extraction with diethyl ether. The organic layer was washed with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 55 mg of ethyl 2-[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]cyclopropanecarboxylate.

후처리

  1. stirringby stirring at room temperature for 1 hour and at 60° C. for 1 hour
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-7a5c91ddafa645bfa7e8da37bc6e7fc9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133882B2

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