Acetonitrile → 7-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

HRID 1267610

반응식

HRID 1267610 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16](F)[CH:17]=2)[C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10]1.[CH3:25][O:26][N:27]=[C:28]1[C:32]2([CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:33]2)[CH2:31][NH:30][CH2:29]1.C(#N)C>C(N(CC)CC)C>[C:39]([O:38][C:36]([N:34]1[CH2:35][C:32]2([C:28](=[N:27][O:26][CH3:25])[CH2:29][N:30]([C:16]3[CH:17]=[C:18]4[C:13]([C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10][N:9]4[C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])=[CH:14][C:15]=3[F:20])[CH2:31]2)[CH2:33]1)=[O:37])([CH3:42])([CH3:41])[CH3:40]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 598041-(2,4-Difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 545476562,6-Diazaspiro[3.4]octane-2-carboxylic acid, 8-(methoxyimino)-, 1,1-dimethylethyl ester

생성물 1

HCID 538300717-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid수율 67.8%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

1-(2,4-difluorophenyl)-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, 120 mg of t-butyl 8-(methoxyimino)-2,6-diazaspiro[3,4]octane-2-carboxylate and 400 mg of AmberliteR IRA-420 were added to 10 ml of acetonitrile and thereto 0.5 ml of triethylamine was added by dropping. The resulting mixture was refluxed for 48 hours and thus precipitated solid was filtered off. To the filtrate 5 ml of ethylether was added and the resulting mixture was stirred for 4 hours. The precipitated solid was filtered and dried to give 110 mg of the titled compound (yield: 67.8%).

후처리

  1. temperatureThe resulting mixture was refluxed for 48 hours
  2. filtrationthus precipitated solid was filtered off
  3. additionTo the filtrate 5 ml of ethylether was added
  4. filtrationThe precipitated solid was filtered
  5. customdried

출처 및 근거

ORD 기록
ord-84c9825d5fa947b5b0f4dca563c85bae
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552196B2

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