Fluoroquinolonic acid → HCID 23042979, compound

HRID 2165693Notes

Reaction equation

HRID 2165693 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)[CH:2]=1.Cl[C:14]1[CH:23]=[C:22]2[C:17]([C:18](=[O:30])[C:19]([C:27]([OH:29])=[O:28])=[CH:20][N:21]2[CH:24]2[CH2:26][CH2:25]2)=[CH:16][C:15]=1[F:31]>N1C=CC=CC=1>[CH:24]1([N:21]2[C:22]3[C:17](=[CH:16][C:15]([F:31])=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[CH2:12]4)[CH:23]=3)[C:18](=[O:30])[C:19]([C:27]([OH:29])=[O:28])=[CH:20]2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 483180Fluoroquinolonic acidHCID 38722892-Pyridin-3-yl-piperazine

Product 1

HCID 23042979HCID 23042979, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 733.5 mg of 2-(3-pyridinyl)piperazine, 421.5 mg of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 10 ml of pyridine was heated at 135° C. for 24 hours. The solvent was removed and the residue purified by chromatography on silica gel using chloroform:methanol:triethylamine:water (9.5:0.5:0.01:0.01), giving 120 mg of the desired product.

Workup

  1. customThe solvent was removed
  2. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c17d476939414631be7f092d29409b9b
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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