7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid → 1-(4-Fluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-[3-(phenoxymethyl)-1-piperazinyl]-3-quinolinecarboxylic acid

HRID 248513

Reaction equation

HRID 248513 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:19]([OH:21])=[O:20])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:23].[O:24]([CH2:31][CH:32]1[NH:37][CH2:36][CH2:35][NH:34][CH2:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[F:23][C:3]1[CH:2]=[CH:11][C:10]([N:9]2[C:12]3[C:17](=[CH:16][C:15]([F:18])=[C:14]([N:34]4[CH2:35][CH2:36][NH:37][CH:32]([CH2:31][O:24][C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH2:33]4)[CH:13]=3)[C:6](=[O:22])[C:7]([C:19]([OH:21])=[O:20])=[CH:8]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 573387-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 197636043-Phenoxymethylpiperazine

Product 1

HCID 148394081-(4-Fluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-[3-(phenoxymethyl)-1-piperazinyl]-3-quinolinecarboxylic acidYield 33.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.6 g of 7-chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.03 g of 3-(phenoxymethyl)piperazine and 5 ml of pyridine was reacted as described in Example 81, giving 295 mg of the desired product, mp 204°-207° C.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-422a095a4f894274b67db3aec64943a1
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Linked notes

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