Diethyl Ether → PD 135042

HRID 358860

반응식

HRID 358860 반응식
[B](F)F.[CH:4]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:20])=[C:14](F)[C:15]=3[O:17][CH3:18])[C:10](=[O:21])[C:9]([C:22]([OH:24])=[O:23])=[CH:8]2)[CH2:6][CH2:5]1.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(OCC)C>CS(C)=O>[CH:4]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:20])=[C:14]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[C:15]=3[O:17][CH3:18])[C:10](=[O:21])[C:9]([C:22]([OH:24])=[O:23])=[CH:8]2)[CH2:6][CH2:5]1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 4837PiperazineHCID 86585298Difluoroborane 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate

생성물 1

HCID 465562PD 135042수율 60.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

0.11 g (0.00032 mole) of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid boron difluoride chelate (IV) (prepared as described in Preparation 7) was dissolved in 0.5 ml of dimethyl sulfoxide, and 0.11 g (0.0012 mole) of anhydrous piperazine was added to the resulting solution. The mixture was then allowed to stand at room temperature overnight, after which it was poured into 50 ml of diethyl ether. The yellow crystals which precipitated were collected by filtration and dissolved in 30 ml of 80% aqueous ethanol and 5 ml of triethylamine, and the resulting solution was heated under reflux for 4 hours. The reaction mixture was then filtered while hot to remove insoluble material, and the filtrate was concentrated by evaporation under reduced pressure to give a crystalline substance, which was washed with ethanol to afford 0.07 g of 1-cyclopropyl-6-fluoro-8-methoxy-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as colorless powdery crystals, melting at 177°-178° C.

후처리

  1. customThe yellow crystals which precipitated
  2. filtrationwere collected by filtration
  3. dissolutiondissolved in 30 ml of 80% aqueous ethanol
  4. temperature5 ml of triethylamine, and the resulting solution was heated
  5. temperatureunder reflux for 4 hours
  6. filtrationThe reaction mixture was then filtered while hot
  7. customto remove insoluble material
  8. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  9. customto give a crystalline substance, which
  10. washwas washed with ethanol

출처 및 근거

ORD 기록
ord-9fea01a665bb4c21ad93924085579c09
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04997943

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