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

HRID 1534818Notes

Reaction equation

HRID 1534818 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 1,8diazabicyclo[5.4.0]undec-7-ene (DBU) were suspended in 32 ml of acetonitrile and the suspension was refluxed for 10 hours. The reaction mixture was kept overnight at room temperature. The produced precipitate was filtered and washed with ethanol. 0.58 g of the titled compound was obtained (yield 74%).

Workup

  1. temperaturethe suspension was refluxed for 10 hours
  2. filtrationThe produced precipitate was filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-365c3758552840258c9eb4a08185c1ed
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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