rel-(2R,6S)-2,6-dimethylpiperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6-fluoro-4-oxo-, cis-

HRID 373523ノート

反応式

HRID 373523 の反応式
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.[CH3:21][C@H:22]1[CH2:27][NH:26][CH2:25][C@@H:24]([CH3:28])[NH:23]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:25][C@H:24]([CH3:28])[NH:23][C@H:22]([CH3:21])[CH2:27]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1

参加物

4

反応物 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

生成物 1

HCID 30788563-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6-fluoro-4-oxo-, cis-収率 66.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 280 mg of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 542 mg of cis-2,6-dimethylpiperazine and 10 ml of pyridine was heated under reflux for 2.5 hours. The solvent was evaporated under reduced pressure. To the residue was added a 1N aqueous solution of sodium hydroxide, and the insoluble matter was removed by filtration. A 10% aqueous solution of acetic acid was added to the filtrate to adjust its pH to 8. The solution was then extracted with chloroform. The chloroform layer was dried with sodium sulfate, and concentrated under reduced pressure. Acetonitrile was added to the residue, and the mixture was cooled with ice. The crystals were collected by filtration, and recrystallized from aqueous ammonia to give 250 mg of 5-amino-1-cyclopropyl-6-fluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 253°-254° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the residue was added a 1N aqueous solution of sodium hydroxide
  5. customthe insoluble matter was removed by filtration
  6. additionA 10% aqueous solution of acetic acid was added to the filtrate
  7. extractionThe solution was then extracted with chloroform
  8. dry with materialThe chloroform layer was dried with sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionAcetonitrile was added to the residue
  11. temperaturethe mixture was cooled with ice
  12. filtrationThe crystals were collected by filtration
  13. customrecrystallized from aqueous ammonia

出典と根拠

ORDレコード
ord-9e68b113ffbf4207a910df4b8698086e
出典データセット
uspto-grants-1992_11
特許番号
US05164392

反応ノート

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