2-Methylpiperazine → 5-Amino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2050630ノート

反応式

HRID 2050630 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][CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:25][CH2:24][NH:23][CH: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 660572-MethylpiperazineHCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

生成物 1

HCID 148802265-Amino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid収率 62.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 1.0 g of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.18 g of 2-methylpiperazine and 10 ml of pyridine was heated under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in 28% aqueous ammonia. The solution was neutralized with a 10% aqueous solution of acetic acid and cooled with ice. The crystals were collected by filtration, dissolved in a 10% aqueous solution of acetic acid, treated with activated charcoal, adjusted to pH 8-9 with 29% aqueous ammonia, and cooled with ice. The crystals were collected by filtration and washed successively with water and ethanol to give 0.80 g of 5-amino-1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 181°-183° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 28% aqueous ammonia
  5. temperaturecooled with ice
  6. filtrationThe crystals were collected by filtration
  7. dissolutiondissolved in a 10% aqueous solution of acetic acid
  8. additiontreated with activated charcoal
  9. temperaturecooled with ice
  10. filtrationThe crystals were collected by filtration
  11. washwashed successively with water and ethanol

出典と根拠

ORDレコード
ord-2415d5ae2e4e4873942c3c83df8efe52
出典データセット
uspto-grants-1991_05
特許番号
US05013841

反応ノート

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