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

HRID 1534823Notes

Reaction equation

HRID 1534823 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Br.Br.[CH2:23]([N:25]1[CH2:32][C:31]2[CH2:30][NH:29][CH2:28][C:27]=2[CH2:26]1)[CH3:24].N12CCCN=C1CCCCC2>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:29]4[CH2:30][C:31]5[CH2:32][N:25]([CH2:23][CH3:24])[CH2:26][C:27]=5[CH2:28]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19908239N-ethyl-3,7-diazabicyclo [3.3.0] oct-1(5)-ene dihydrobromide

Product 1

HCID 199082411-Cyclopropyl-6,8-difluoro-7-[7-ethyl-3,7-diazabicyclo [3.3.0] oct-1(5)-en-3-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 73.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.48 g), N-ethyl-3,7-diazabicyclo [3.3.0] oct-1(5)-ene dihydrobromide (0.57 g) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU, 0.87 ml) were dissolved in acetonitrile (20 ml) and refluxed for 3 hours. After cooling the reaction mixture, the produced precipitate was collected by filteration and washed with acetonitrile (10 ml) and methanol (10 ml) to give the title compound (0.5 g, yield 73%)

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling the reaction mixture
  3. customthe produced precipitate was collected by filteration
  4. washwashed with acetonitrile (10 ml) and methanol (10 ml)

Sources & evidence

ORD record
ord-59be8c569d694dd39628bbb6f1c90981
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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