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

HRID 2165671Notes

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][C:22]([CH:25]2[NH:30][CH2:29][CH2:28][NH:27][CH2:26]2)=[CH:21]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[CH2:28][CH2:29][NH:30][CH:25]([C:22]5[CH:23]=[CH:24][O:20][CH:21]=5)[CH2:26]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

Conditions

Temperature: 120 °C

Procedure

A mixture of 365 mg of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 593 mg of 3-(3-furanyl)piperazine and 10 ml of pyridine was heated in a pressure bottle at about 120° C. for 2 days, then allowed to cool and the solvent removed. The residue was purified by flash silica gel column chormatography eluting with chloroform:methanol:water:triethylamine (95:5:1:1). This product was then triturated with methanol-ether and the solid, washed with methanol, then ether and dried in vacuo, giving 125 mg of the desired product, mp 202°-204° C.

Workup

temperatureto cool
customthe solvent removed
customThe residue was purified by flash silica gel column chormatography
washeluting with chloroform:methanol:water:triethylamine (95:5:1:1)
customThis product was then triturated with methanol-ether
washthe solid, washed with methanol
dry with materialether and dried in vacuo

Sources & evidence

ORD record: ord-17aaa9d9baf8433098bdfaadf53889de
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04940710

Reaction notes

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