1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-7-[3-(2-fluoroethyl)aminomethyl-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 414218Notes

Reaction equation

HRID 414218 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.[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>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:28]4[CH2:29][CH2:30][CH:26]([CH2:25][NH:24][CH2:23][CH2:22][F:21])[CH2:27]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 143077563-(2-Fluoroethylaminomethyl)pyrrolidine

Product 1

HCID 139338091-Cyclopropyl-7-[3-(2-fluoroethyl)aminomethyl-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 48.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-cyclopropyl-6,7,8-trifluoro-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 (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 (140 mg), mp 134°-138° 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-515b307af6b4476e9316992037373974
Source dataset
uspto-grants-1988_12
Patent number
US04791118

Reaction notes

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