Water → Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 232496노트

반응식

HRID 232496 반응식
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:24]2[C:19](=[CH:20][C:21]([F:44])=[C:22](OS(C3C(C(C)C)=CC(C(C)C)=CC=3C(C)C)(=O)=O)[N:23]=2)[C:18](=[O:45])[C:17]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:16]1.C(OCC)(=O)C.O>C(Cl)Cl.C(OCC)C>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:24]2[C:19](=[CH:20][C:21]([F:44])=[C:22]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)[N:23]=2)[C:18](=[O:45])[C:17]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:16]1

참가 물질

7

반응물 4

HCID 962WaterHCID 4837PiperazineHCID 8857Ethyl AcetateHCID 13849335Ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(2,4,6-triisopropylbenzenesulfonyloxy)-1,8-naphthyridine-3-carboxylate

생성물 1

HCID 13849334Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate수율 91.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

In 4 ml of methylene chloride was dissolved 270 mg of anhydrous piperazine, and 400 mg of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(2,4,6-triisopropylbenzenesulfonyloxy)-1,8-naphthyridine-3-carboxylate was added to the resulting solution, after which the resulting mixture was subjected to reaction with ice-cooling for 1 hour. To the reaction mixture were added 20 ml of ethyl acetate and 10 ml of water, and the organic layer was separated, washed successively with 10 ml of saturated aqueous sodium hydrogencarbonate solution and 10 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 5 ml of diethyl ether, after which crystals were collected by filtration to obtain 250 mg (yield 91.2%) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate having a melting point of 208°-211° C.

후처리

  1. additionwas added to the resulting solution
  2. customafter which the resulting mixture was subjected to reaction with ice-
  3. temperaturecooling for 1 hour
  4. customthe organic layer was separated
  5. washwashed successively with 10 ml of saturated aqueous sodium hydrogencarbonate solution and 10 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customto the crystalline material thus obtained
  9. filtrationafter which crystals were collected by filtration

출처 및 근거

ORD 기록
ord-cfe286a492bb46feab1629d1f0a96f97
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851535

반응 노트

불러오는 중…