7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-[3-(5-Bromo-2-thienyl)-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 248467노트

반응식

HRID 248467 반응식
[Br:1][C:2]1[S:6][C:5]([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.Cl[C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]2[CH2:24][CH3:25])=[CH:16][C:15]=1[F:30]>N1C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([CH:7]2[NH:8][CH2:9][CH2:10][N:11]([C:14]3[CH:23]=[C:22]4[C:17]([C:18](=[O:29])[C:19]([C:26]([OH:28])=[O:27])=[CH:20][N:21]4[CH2:24][CH3:25])=[CH:16][C:15]=3[F:30])[CH2:12]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197636062-(5-Bromothiophen-2-yl)piperazine

생성물 1

HCID 148393577-[3-(5-Bromo-2-thienyl)-1-piperazinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A 3 g portion of 2-(5-bromo-2-thienyl)piperazine was suspended in 8 ml of dry pyridine. An 820 mg portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated in a pressure bottle, under argon, at 120°-130° C. for 18 hours, then cooled, filtered and evaporated to dryness. The residue was evaporated from toluene and this residue purified by chromatography, eluting with chloroform:water saturated methanol (9:1). The appropriate fractions were combined, evaporated and recrystallized from dimethylformamide-ether, giving 440 mg of the desired product, mp 233°-235° C. (dec.).

후처리

  1. temperaturethe mixture was heated in a pressure bottle, under argon, at 120°-130° C. for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was evaporated from toluene
  6. customthis residue purified by chromatography
  7. washeluting with chloroform
  8. customevaporated
  9. customrecrystallized from dimethylformamide-ether

출처 및 근거

ORD 기록
ord-62e553e0534042cb81e8b5f28c252a13
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210193

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