1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 3073581, compound

HRID 1534828Notes

Reaction equation

HRID 1534828 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.[CH3:23][N:24]1[CH2:31][C:30]2[CH2:29][NH:28][CH2:27][C:26]=2[CH2:25]1.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:28]4[CH2:29][C:30]5[CH2:31][N:24]([CH3:23])[CH2:25][C:26]=5[CH2:27]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]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 19908242HCID 19908242, compound

Product 1

HCID 3073581HCID 3073581, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.42 g), 3-methyl-3,7-diazabicyclo[3.3.0]oct-1(5)-ene dihydrobromide (0.47 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.63 g) were dissolved in acetonitrile (20 ml) and refluxed for 7 hours. The reaction mixture was kept at room temperature overnight and then the produced precipitate was filtered, washed with acetonitrile and methanol to give the title compound 0.36 g (yield 62%).

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationthe produced precipitate was filtered
  3. washwashed with acetonitrile and methanol

Sources & evidence

ORD record
ord-dd4c298e5fd24daeac5fe0d66a03be4e
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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