1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-[2,5-Diazabicyclo(2.2.1)hept-2-yl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1589569Notes

Reaction equation

HRID 1589569 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].Br.Br.[CH:22]12[CH2:28][CH:25]([NH:26][CH2:27]1)[CH2:24][NH:23]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:22]12[CH2:28][CH:25]([NH:26][CH2:27]1)[CH2:24][N:23]2[C:10]1[C:11]([F:13])=[C:12]2[C:7]([C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4][N:3]2[CH2:1][CH3:2])=[CH:8][C:9]=1[F:15]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 16213147HCID 16213147, compound

Product 1

HCID 135658007-[2,5-Diazabicyclo(2.2.1)hept-2-yl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.54 g (2.0 mmol) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.57 g (2.2 mmol) of 2,5-diazabicyclo(2.2.1)heptane dihydrobromide [P. S. Portoghese and A. A. Mikhail, J. Org. Chem., 31, 1059 (1966)], 0.90 ml (6.0 mmol) of 1,8-diazabicyclo(5.4.0)undec-7ene, and 20 ml of acetonitrile was heated under reflux for one hour and stirred at room temperature for two hours. The reaction mixture was filtered and the solid was washed with ethanol to give 0.60 g of the title compound, mp 275° C.

Workup

  1. temperatureunder reflux for one hour
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with ethanol

Sources & evidence

ORD record
ord-5552fe03e13f4ff29bde74b4d71cd05e
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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