1-Methylpiperazine → 1-Cyclopropyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 358861

反応式

HRID 358861 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:8]1([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:24])=[C:18](F)[C:19]=3[O:21][CH3:22])[C:14](=[O:25])[C:13]([C:26]([OH:28])=[O:27])=[CH:12]2)[CH2:10][CH2:9]1>CS(C)=O>[CH:8]1([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:24])=[C:18]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)[C:19]=3[O:21][CH3:22])[C:14](=[O:25])[C:13]([C:26]([OH:28])=[O:27])=[CH:12]2)[CH2:10][CH2:9]1

参加物

4

反応物 2

HCID 531671-MethylpiperazineHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

生成物 1

HCID 107382321-Cyclopropyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid収率 26.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
70 °C

実験手順

0.12 g (0.0012 mole) of N-methylpiperazine was added to a solution of 0.09 g (0.0003 mole) of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (IIc) (prepared as described in Preparation 6) in 0.5 ml of dimethyl sulfoxide, and the mixture was stirred at 70° C. for 6 hours. At the end of this time, the solvent and the excess N-methylpiperazine were removed by evaporation under reduced pressure at the same temperature, and the residue was washed with ethyl acetate and subjected to silica gel column chromatography, eluted with methanol, to afford 0.03 g of 1-cyclopropyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as colorless powdery crystals, melting at 211°-214° C.

後処理

  1. customAt the end of this time, the solvent and the excess N-methylpiperazine were removed by evaporation under reduced pressure at the same temperature
  2. washthe residue was washed with ethyl acetate
  3. washeluted with methanol

出典と根拠

ORDレコード
ord-dc86e9022bf84fd284bba053d3080fcf
出典データセット
uspto-grants-1991_03
特許番号
US04997943

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