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1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580587
Notes
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Reaction equation

HRID 580587 reaction equation
[Br: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].C(OC([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][NH:31][CH2:30]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][N:31]([C:3]2[C:2]([Br:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[CH:5][C:4]=2[F:19])[CH2:30]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidineHCID 137488068-Bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 703541507-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 25.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.19 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.14 g), DBU (0.095 g) and anhydrous acetonitrile (5 ml) was refluxed for 2 hours and then concentrated. The resulting residue was dissolved in chloroform (70 ml), washed with 10% aqueous citric acid solution, water successively, dried over anhydrous sodium sulfate and then concentrated. To the resulting oily residue was added hot methanol to crystallize and cooled. The resulting precipitate was collected by filtration, added to the mixture of concentrated hydrochloric acid-methanol (1:1, 3 ml) and stirred for 2.5 hours under elevated temperature. The reaction mixture was neutralized with concentrated aqueous ammonia, the resulting precipitate was collected by filtration, washed with ice-water and recrystallized from dichloromethane-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.06 g) as yellow prisms, mp 225°-226.5° C. (decompd.).

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in chloroform (70 ml)
  4. washwashed with 10% aqueous citric acid solution, water successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additionTo the resulting oily residue was added hot methanol
  8. customto crystallize
  9. temperaturecooled
  10. filtrationThe resulting precipitate was collected by filtration
  11. additionadded to the mixture of concentrated hydrochloric acid-methanol (1:1, 3 ml)
  12. filtrationthe resulting precipitate was collected by filtration
  13. washwashed with ice-water
  14. customrecrystallized from dichloromethane-methanol-concentrated aqueous ammonia (10:10:1)

Sources & evidence

ORD record
ord-044fb902b5d442b0981969a9b1580ca0
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04753953

Reaction notes

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