1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-6-fluoro-8-methoxy-7-{3-[(methylamino)methyl]pyrrolidin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 2249248

Reaction equation

HRID 2249248 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:22][NH:23][CH2:24][CH:25]1[CH2:29][CH2:28][NH:27][CH2:26]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([N:27]4[CH2:28][CH2:29][CH:25]([CH2:24][NH:23][CH3:22])[CH2:26]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 13491795N-Methyl-1-(pyrrolidin-3-yl)methanamine

Product 1

HCID 4834131-Cyclopropyl-6-fluoro-8-methoxy-7-{3-[(methylamino)methyl]pyrrolidin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 49.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (200 mg), 3-methylaminomethylpyrrolidine (90 mg), DBU (110 mg) and anhydrous acetonitrile (3 ml) was refluxed for 75 minutes. After cooling, the resulting precipitate was collected by filtration and recrystallized from a solution of dichloromethane-methanol (1:1) to give the title compound (130 mg) as white powdery crystals, mp 226.5°-230° C.

Workup

  1. temperaturewas refluxed for 75 minutes
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was collected by filtration
  4. customrecrystallized from a solution of dichloromethane-methanol (1:1)

Sources & evidence

ORD record
ord-df923ee056214776bad916cd779a74a0
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Linked notes

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