1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19908249, compound

HRID 1534825Notes

Reaction equation

HRID 1534825 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:21])=[C:16](F)[C:17]=2[F:19])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]1.Br.Br.[C:28]12[CH2:35][NH:34][CH2:33][C:32]=1[CH2:31][NH:30][CH2:29]2.N12CCCN=C1CCCCC2>C(#N)C>[C:28]12[CH2:35][NH:34][CH2:33][C:32]=1[CH2:31][N:30]([C:7]1[C:2]([F:1])=[C:3]3[C:4]([C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10][N:9]3[C:18]3[CH:13]=[CH:14][C:15]([F:21])=[CH:16][C:17]=3[F:19])=[CH:5][C:6]=1[F:8])[CH2:29]2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 144760111-(2,4-Difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Product 1

HCID 19908249HCID 19908249, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2,4-Difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.07 g), 3,7-diazabicyclo [3.3.0] oct-1(5)-ene dihydrobromide (1 g) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU, 2 ml) were dissolved in acetonitrile (30 ml) and refluxed for 7 hours. The reaction mixture was kept overnight at room temperature and the produced precipitate was filtered and then suspended in methanol (10 ml) and sonicated for 30 minutes. The insoluble product was collected by filtration to give the title compound (1 g, yield 74%).

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationthe produced precipitate was filtered
  3. customsonicated for 30 minutes
  4. filtrationThe insoluble product was collected by filtration

Sources & evidence

ORD record
ord-5322af0bbece4042b38d3580f32a7d58
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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