1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 14652609, compound

HRID 477849Notes

Reaction equation

HRID 477849 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.Cl.Cl.[CH3:28][NH:29][CH2:30][CH:31]1[O:36][CH2:35][CH2:34][NH:33][CH2:32]1.N12CCCN=C1CCCCC2>C(#N)C>[F:19][C:17]1[CH:16]=[C:15]([F:21])[CH:14]=[CH:13][C:18]=1[N:9]1[C:3]2[C:4](=[CH:5][C:6]([F:8])=[C:7]([N:33]3[CH2:34][CH2:35][O:36][CH:31]([CH2:30][NH:29][CH3:28])[CH2:32]3)[C:2]=2[F:1])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]1

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 14652584HCID 14652584, compound

Product 1

HCID 14652609HCID 14652609, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 710 mg of 1-(2,4-difluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 487 mg of 2-(methylaminomethyl)morpholine dihydrochloride and 1035 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene in 10 ml of acetonitrile is refluxed for 21 hours. The reaction mixture is concentrated under reduced pressure and to the residue is added 10 ml of methanol. The obtained crystals are collected by filtration and washed with methanol, water and then acetone to give 1-(2,4-difluorophenyl)-7-[2-(methylaminomethyl)morpholino]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, melting at 224°-227° C. with decomposition.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure and to the residue
  2. additionis added 10 ml of methanol
  3. filtrationThe obtained crystals are collected by filtration
  4. washwashed with methanol, water

Sources & evidence

ORD record
ord-b1d75cb5008449d7b3adb2e01b34c828
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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