1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1589564

反応式

HRID 1589564 の反応式
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].Cl.Cl.[CH:21]12[CH2:28][CH2:27][CH:24]([NH:25][CH2:26]1)[CH2:23][NH:22]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:21]12[CH2:28][CH2:27][CH:24]([NH:25][CH2:26]1)[CH2:23][N:22]2[C:10]1[CH:11]=[C:12]2[C:7]([C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4][N:3]2[CH2:1][CH3:2])=[CH:8][C:9]=1[F:14]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 229243902,5-Diazabicyclo(2.2.2)octane dihydrochloride

生成物 1

HCID 135657957-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid収率 43.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 0.52 g (2.0 mmole) of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.37 g (2.0 mmole) of 2,5-diazabicyclo(2.2.2)octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 0.90 ml (6.0 mmole) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 25 ml of acetonitrile was heated under reflux for 21 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was recrystallized from ethanol to give 0.30 g of the title compound, mp 270°-272°.

後処理

  1. temperatureunder reflux for 21 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-9cd97c866e664a92aa9f435b7db69aaf
出典データセット
uspto-grants-1986_02
特許番号
US04571396

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