Fluoroquinolonic acid → HCID 14839405, compound

HRID 2165662Notes

Reaction equation

HRID 2165662 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH3:20][O:21][CH2:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>N1C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:27]4[CH2:26][CH2:25][NH:24][CH:23]([CH2:22][O:21][CH3:20])[CH2:28]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 483180Fluoroquinolonic acidHCID 142302642-(Methoxymethyl)piperazine

Product 1

HCID 14839405HCID 14839405, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.6 g of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 1.4 g of 2-(methoxymethyl)piperazine in 4 ml of pyridine was heated at 120°-130° C. under argon in a pressure bottle for 18 hours. The solvent was removed and the residue was chromatographed and the crude product triturated with methanol and ether, giving 370 mg of the desired product as white crystals, mp 215°-216° C.

Workup

  1. temperaturewas heated at 120°-130° C. under argon in a pressure bottle for 18 hours
  2. customThe solvent was removed
  3. customthe residue was chromatographed
  4. customthe crude product triturated with methanol and ether

Sources & evidence

ORD record
ord-691674d653b242c89dd82ffce57ff262
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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