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

HRID 246975ノート

反応式

HRID 246975 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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 crystlaline 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.

後処理

  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 crystlaline material thus obtained
  9. filtrationafter which crystals were collected by filtration

出典と根拠

ORDレコード
ord-1696355d8464460a8e7ae7c4c1979efb
出典データセット
uspto-grants-1987_11
特許番号
US04704459

反応ノート

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