1,8-Diazabicyclo(5.4.0)undec-7-ene → 6,8-Difluoro-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534829Notes

Reaction equation

HRID 1534829 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=2[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]1.Br.Br.[C:23]12[CH2:30][NH:29][CH2:28][C:27]=1[CH2:26][NH:25][CH2:24]2.N12CCCN=C1CCCCC2>C(#N)C>[F:16][C:10]1[CH:9]=[C:8]2[C:13](=[C:12]([F:14])[C:11]=1[N:25]1[CH2:26][C:27]3[CH2:28][NH:29][CH2:30][C:23]=3[CH2:24]1)[N:4]([CH2:3][CH2:2][F:1])[CH:5]=[C:6]([C:18]([OH:20])=[O:19])[C:7]2=[O:17]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 127709081-(2-Fluoroethyl)-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 199082516,8-Difluoro-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 76.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Fluoroethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.29 g), 3,7-diazabicyclo [3.3.0]oct-1(5)-ene dihydrobromide (0.33 g) and 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU, 0.46 g) were dissolved in acetonitrile (15 ml) and refluxed for 3 hours. The reaction mixture was kept at room temperature overnight and the precipitate was collected by filtration, washed with acetonitrile and methanol to give the title compound (0.29 g, yield 76%).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with acetonitrile and methanol

Sources & evidence

ORD record
ord-6416c824505e420f8424088b7a79e251
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

Loading…