1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 13933808, compound

HRID 414217Notes

Reaction equation

HRID 414217 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].[F:21][CH2:22][CH2:23][NH:24][CH2:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[Cl:1][C:2]1[C:3]([N:28]2[CH2:29][CH2:30][CH:26]([CH2:25][NH:24][CH2:23][CH2:22][F:21])[CH2:27]2)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 143077563-(2-Fluoroethylaminomethyl)pyrrolidine

Product 1

HCID 13933808HCID 13933808, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (200 mg), 3-(2-fluoroethylaminomethyl)pyrrolidine (165 mg) and 1,8-diazabicyclo[5,4,0]-7-undecene (DBU, 100 mg) in absolute acetonitrile (2 ml) was refluxed for an hour. After cooling, the reaction mixture was concentrated and to the residue was added acetonitrile-ether (1:1, 5 ml). The solution was allowed to stand overnight at 5° C., then the resulting precipitate was collected by filtration and recrystallized from chloroform-methanol-ether to give the title compound (40 mg), mp 138°-142° C.

Workup

  1. temperaturewas refluxed for an hour
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated and to the residue
  4. additionwas added acetonitrile-ether (1:1, 5 ml)
  5. filtrationthe resulting precipitate was collected by filtration
  6. customrecrystallized from chloroform-methanol-ether

Sources & evidence

ORD record
ord-a23998073d0c4969b1171cd5c3a272b3
Source dataset
uspto-grants-1988_12
Patent number
US04791118

Reaction notes

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