1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-[3,7-Diazabicyclo [3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534824Notes

Reaction equation

HRID 1534824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)=[CH:4][CH:3]=1.Br.Br.[C:27]12[CH2:34][NH:33][CH2:32][C:31]=1[CH2:30][NH:29][CH2:28]2.N12CCCN=C1CCCCC2>C(#N)C>[C:27]12[CH2:34][NH:33][CH2:32][C:31]=1[CH2:30][N:29]([C:15]1[C:16]([F:18])=[C:17]3[C:12]([C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9][N:8]3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:13][C:14]=1[F:20])[CH2:28]2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Product 1

HCID 539601277-[3,7-Diazabicyclo [3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.33 g), 3,7-diazabicyclo[3.3.0] oct-1(5)-ene dihydrobromide (0.27 g) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU, 1 ml) were dissolved in acetonitrile (10 ml) and refluxed for 4 hours. The reaction mixture was kept overnight at room temperature and the produced precipitate was filtered, washed with acetonitrile, methanol to give the title compound (0.28 g, yield 66%).

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationthe produced precipitate was filtered
  3. washwashed with acetonitrile, methanol

Sources & evidence

ORD record
ord-70256878ca214818b55261bc29b5c118
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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