Fluoroquinolonic acid → 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-furanyl)-1-piperazinyl]-3-quinolinecarboxylic acid

HRID 2165671노트

반응식

HRID 2165671 반응식
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[O:20]1[CH:24]=[CH:23][C:22]([CH:25]2[NH:30][CH2:29][CH2:28][NH:27][CH2:26]2)=[CH:21]1>N1C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:27]4[CH2:28][CH2:29][NH:30][CH:25]([C:22]5[CH:23]=[CH:24][O:20][CH:21]=5)[CH2:26]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

참가 물질

4

반응물 2

HCID 483180Fluoroquinolonic acidHCID 197635372-(Furan-3-yl)piperazine

생성물 1

HCID 148394111-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(3-furanyl)-1-piperazinyl]-3-quinolinecarboxylic acid수율 24.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
120 °C

실험 절차

A mixture of 365 mg of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 593 mg of 3-(3-furanyl)piperazine and 10 ml of pyridine was heated in a pressure bottle at about 120° C. for 2 days, then allowed to cool and the solvent removed. The residue was purified by flash silica gel column chormatography eluting with chloroform:methanol:water:triethylamine (95:5:1:1). This product was then triturated with methanol-ether and the solid, washed with methanol, then ether and dried in vacuo, giving 125 mg of the desired product, mp 202°-204° C.

후처리

  1. temperatureto cool
  2. customthe solvent removed
  3. customThe residue was purified by flash silica gel column chormatography
  4. washeluting with chloroform:methanol:water:triethylamine (95:5:1:1)
  5. customThis product was then triturated with methanol-ether
  6. washthe solid, washed with methanol
  7. dry with materialether and dried in vacuo

출처 및 근거

ORD 기록
ord-17aaa9d9baf8433098bdfaadf53889de
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940710

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