1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(8-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-3-quinolinecarboxylic acid

HRID 1589576Notes

Reaction equation

HRID 1589576 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].Cl.Cl.[CH3:22][N:23]1[CH:28]2[CH2:29][CH2:30][CH:24]1[CH2:25][NH:26][CH2:27]2>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([CH:25]3[NH:26][CH2:27][CH:28]4[N:23]([CH3:22])[CH:24]3[CH2:30][CH2:29]4)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

Product 1

HCID 135658271-Ethyl-6,8-difluoro-1,4-dihydro-7-(8-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-3-quinolinecarboxylic acidYield 44.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.40 g (5.0 mmole) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 2.0 g (8 mmole) of 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 2.0 ml (13.3 mmole) of 1,8-diazobicyclo[5.4.0]undec-7-ene, and 75 ml of acetonitrile was heated under reflux for 1.5 hr and then stirred at room temperature for 22 hours. The reaction mixture was evaporated to dryness and the residue was recrystallized from 2-propanol to give 0.84 g of the title compound, mp 184°-187° C.

Workup

  1. temperatureunder reflux for 1.5 hr
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-38223ad0e8c44edbb068c3a662af735e
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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