1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19908253, compound

HRID 1534819Notes

Reaction equation

HRID 1534819 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Br.C([N:29]1[CH2:37][CH2:36][C:35]2[CH2:34][NH:33][CH2:32][C:31]=2[CH2:30]1)C1C=CC=CC=1.N12CCCN=C1CCCCC2>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:33]4[CH2:32][C:31]5[CH2:30][NH:29][CH2:37][CH2:36][C:35]=5[CH2:34]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19908256HCID 19908256, compound

Product 1

HCID 19908253HCID 19908253, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.3 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 0.6 g of 3-benzyl-3,8-diazabicyclo[4.3.0] non-1(6)-ene hydrobromide were suspended in 30 ml of acetonitrile. 0.6 ml of 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) was added to the suspension. The reaction mixture was refluxed for 5 hours and then kept overnight at room temperature. The produced precipitate was filtered and dissolved in 30 ml of 5% acetic acid in ethanol. After adding 0.5 g of 10% palladium charcoal, the reaction mixture was stirred under the hydrogen stream for 6 hours and then filtered. The filtrate was concentrated under reduced pressure. 0.25 g of the title compound was obtained (yield 61%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. filtrationThe produced precipitate was filtered
  3. dissolutiondissolved in 30 ml of 5% acetic acid in ethanol
  4. additionAfter adding 0.5 g of 10% palladium charcoal
  5. waitstream for 6 hours
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-706be939c5dd4c1cb1cb01867d7a4a69
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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