Fluoroquinolonic acid → 1-Cyclopropyl-6-fluoro-7-[3-(2-furanyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165652Notes

Reaction equation

HRID 2165652 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].[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]1[CH2:30][NH:29][CH2:28][CH2:27][NH:26]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:29]4[CH2:28][CH2:27][NH:26][CH:25]([C:21]5[O:20][CH:24]=[CH:23][CH:22]=5)[CH2:30]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 167407772-(Furan-2-yl)piperazine

Product 1

HCID 148394021-Cyclopropyl-6-fluoro-7-[3-(2-furanyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 23.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 843 mg of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 2.28 g of 2-furanylpiperazine and 10 ml of pyridine was heated in a pressure bottle for 24 hours, then cooled first to room temperature and then at 0° C. The pyridine was removed under reduced pressure and the residue purified by flash column chromatography using chloroform:methanol:water:triethylamine (95:5:.1:.1), giving 280 mg of the desired product, mp 176° C.

Workup

  1. temperaturewas heated in a pressure bottle for 24 hours
  2. customat 0° C
  3. customThe pyridine was removed under reduced pressure
  4. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-9359caa71f7d40c086dbb764cb7cc512
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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