Trimethylsilyl iodide → 7-[3-(Butoxycarbonyl)amino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 483291노트

반응식

HRID 483291 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20]C)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.I[Si](C)(C)C.C(=O)(O)O.[CH2:31]([O:35][C:36]([NH:38][CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1)=[O:37])[CH2:32][CH2:33][CH3:34]>ClCCl.C(#N)C>[CH2:31]([O:35][C:36]([NH:38][CH:39]1[CH2:43][CH2:42][N:41]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:16])[CH2:40]1)=[O:37])[CH2:32][CH2:33][CH3:34]

참가 물질

6

반응물 3

HCID 85247Trimethylsilyl iodideHCID 13590045Methyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateHCID 202428763-Butoxycarbonylaminopyrrolidine bicarbonate

생성물 1

HCID 135900477-[3-(Butoxycarbonyl)amino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid수율 82.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1.0 g (3.4 mmole) of methyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 25 ml dichloromethane was added 0.6 ml (0.8 g, 4.2 mmole) of iodotrimethylsilane while stirring at room temperature under a nitrogen atmosphere. The mixture was warmed to reflux and stirred overnight. The reaction was cooled to room temperature, concentrated, and the residue taken up in 25 ml acetonitrile. To the resulting suspension was added a solution of 1.6 g (8.5 mmole) of 3-butoxycarbonylaminopyrrolidine bicarbonate in 10 ml acetonitrile while under nitrogen. The reaction was warmed to reflux for four hours, then cooled to room temperature. The formed precipitate was filtered, washed with acetonitrile and ether, yielding 1.26 g (82%) of 7-[3-(butoxycarbonyl)amino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 228°-230° C.

후처리

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. stirringstirred overnight
  4. temperatureThe reaction was cooled to room temperature
  5. concentrationconcentrated
  6. temperatureThe reaction was warmed
  7. temperatureto reflux for four hours
  8. temperaturecooled to room temperature
  9. filtrationThe formed precipitate was filtered
  10. washwashed with acetonitrile and ether

출처 및 근거

ORD 기록
ord-311d3045bb5b48d5906a463369469790
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04578473

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