2-Methylpiperazine → Gatifloxacin

HRID 1111449Notes

Reaction equation

HRID 1111449 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][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([N:27]4[CH2:26][CH2:25][NH:24][CH:23]([CH3:22])[CH2:28]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

4

Reactant 2

HCID 660572-MethylpiperazineHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 5379GatifloxacinYield 19.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (200 mg), 2-methylpiperazine (140 mg) and anhydrous DMSO (3 ml) was stirred for 2 hours at 70° to 95° C. on an oil bath. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1), the residue was recrystallized from methanol to give the title compound (50 mg) as white powdery crystals, mp 162° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography
  3. washeluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1)
  4. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e194e41b87344553bb2153cd9f0e181d
Source dataset
uspto-grants-1990_12
Patent number
US04980470

Reaction notes

Loading…