Fluoroquinolonic acid → HCID 70454197, compound

HRID 1284502Notes

Reaction equation

HRID 1284502 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].[CH2:20]([CH:22]1[CH2:27][NH:26][CH2:25][CH2:24][NH:23]1)[CH3:21]>CS(C)=O>[OH2:16].[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:26]4[CH2:25][CH2:24][NH:23][CH:22]([CH2:20][CH3:21])[CH2:27]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 140941882-Ethylpiperazine

Product 1

HCID 70454197HCID 70454197, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.8 g (0.01 mol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 3.4 g (0.03 mol) of 2-ethylpiperazine in 15 ml of dimethylsulphoxide is heated at 140° C. for 2 hours. The solution is concentrated under a high vacuum, the residue is heated to 90° C. with 30 ml of water and the precipitate which has separated out is filtered off with suction, washed with methanol and water and isolated. 1.1 g (31% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-ethyl-1-piperazinyl)-3-quinolinecarboxylic acid monohydrate of decomposition point 255°-258° C. are obtained.

Workup

  1. concentrationThe solution is concentrated under a high vacuum
  2. temperaturethe residue is heated to 90° C. with 30 ml of water
  3. customthe precipitate which has separated out
  4. filtrationis filtered off with suction
  5. washwashed with methanol and water
  6. customisolated

Sources & evidence

ORD record
ord-f08ea848a335428e83fb1034649c55a8
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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