1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19908258, compound

HRID 1534657Notes

Reaction equation

HRID 1534657 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.Br.Br.[C:24]12[CH2:31][NH:30][CH2:29][C:28]=1[CH2:27][NH:26][CH2:25]2.N12CCCN=C1CCCCC2>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([N:26]4[CH2:27][C:28]5[CH2:29][NH:30][CH2:31][C:24]=5[CH2:25]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 138255151-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Product 1

HCID 19908258HCID 19908258, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.6 g of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.2 g of 3,7-diazabicyclo[3.3.0]oct-1(5)-ene dihydrobromide and 1.3 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were suspended in 20 ml of acetonitrile, and then the reaction mixture was refluxed for 10 hours. This reaction mixture was kept overnight at the room temperature, and the produced precipitate was filtered and then the residue was washed with ethanol to obtain 0.58 g the title compound (yield 74%).

Workup

  1. temperaturethe reaction mixture was refluxed for 10 hours
  2. filtrationthe produced precipitate was filtered
  3. washthe residue was washed with ethanol

Sources & evidence

ORD record
ord-30ebb539c8f8440f8f0779760f4e43b4
Source dataset
uspto-grants-1992_02
Patent number
US05089621

Reaction notes

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