7,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid → 7-Fluoro-1-methyl-8-[4-[3-(methylsulfanylmethyl)phenyl]piperazin-1-yl]-4-oxo-benzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 1266161Notes

Reaction equation

HRID 1266161 reaction equation
[F:1][C:2]1[C:20](F)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[CH3:22][S:23][CH2:24][C:25]1[CH:26]=[C:27]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:28]=[CH:29][CH:30]=1>CS(C)=O>[F:1][C:2]1[C:20]([N:34]2[CH2:33][CH2:32][N:31]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][S:23][CH3:22])[CH:26]=3)[CH2:36][CH2:35]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 111970267,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 18549162[3-(Methylsulphanylmethyl)phenyl]piperazine

Product 1

HCID 4840697-Fluoro-1-methyl-8-[4-[3-(methylsulfanylmethyl)phenyl]piperazin-1-yl]-4-oxo-benzo[b][1,8]naphthyridine-3-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

7-Fluoro-1-methyl-8-[4-[3-(methylsulphanylmethyl)phenyl]piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 1, but from 0.45 g of 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 0.66 g of [3-(methylsulphanylmethyl)phenyl]piperazine in 15 cm3 of dimethyl sulphoxide. After washing 2 times with 15 cm3 of ethanol, 0.61 g of 7-fluoro-1-methyl-8-[4-[3-(methylsulphanylmethyl)phenyl]piperazin-1-yl]-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine-3-carboxylic acid was obtained in the form of a yellow solid melting at about 240-5° C.

Workup

  1. custom7-Fluoro-1-methyl-8-[4-[3-(methylsulphanylmethyl)phenyl]piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 1
  2. washAfter washing 2 times with 15 cm3 of ethanol

Sources & evidence

ORD record
ord-f0740eb654a04280bdada8b6d3dc0c8c
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

Loading…