1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 14773872, compound

HRID 330092Notes

Reaction equation

HRID 330092 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[CH3:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:20]([O:24][C:25]([NH:27][CH:28]1[CH2:32][CH2:31][N:30]([C:10]2[C:11]([CH3:13])=[C:12]3[C:7]([C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:15])[CH2:29]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 14052581HCID 14052581, compound

Product 1

HCID 14773872HCID 14773872, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-ethyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylic acid (420 mg), 3-t-butoxycarbonylaminopyrrolidine (350 mg), DBU (260 mg) and anhydrous acetonitrile (10 ml) was refluxed for 35 hours. After the reacting mixture was concentrated under reduced pressure, the resulting residue was dissolved in chloroform (40 ml), washed with 10% aqueous citric acid solution and saturated aqueous sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting chloroform-methanol-concentrated aqueous ammonia (20:6:1) and recrystallized from methanol to give 7-(3-t-butoxycarbonylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylic acid (360 mg) as white prisms, mp 184.5°-187.5° C. (decompd.).

Workup

  1. temperaturewas refluxed for 35 hours
  2. concentrationAfter the reacting mixture was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in chloroform (40 ml)
  4. washwashed with 10% aqueous citric acid solution and saturated aqueous sodium chloride solution successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washeluting chloroform-methanol-concentrated aqueous ammonia (20:6:1)
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e2fff49150c24183ba90ee216fb84d81
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

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