2-(3-Fluorophenyl)piperazine → (RS)-1-ethyl-7-fluoro-8-[3-(3-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid

HRID 344857Notes

Reaction equation

HRID 344857 reaction equation
[CH2:1]([N:3]1[C:12]2[N:11]=[C:10]3[CH:13]=[C:14](F)[C:15]([F:17])=[CH:16][C:9]3=[CH:8][C:7]=2[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1)[CH3:2].[F:23][C:24]1[CH:25]=[C:26]([CH:30]2[CH2:35][NH:34][CH2:33][CH2:32][NH:31]2)[CH:27]=[CH:28][CH:29]=1>>[CH2:1]([N:3]1[C:12]2[N:11]=[C:10]3[CH:13]=[C:14]([N:34]4[CH2:33][CH2:32][NH:31][CH:30]([C:26]5[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=5)[CH2:35]4)[C:15]([F:17])=[CH:16][C:9]3=[CH:8][C:7]=2[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 34578962-(3-Fluorophenyl)piperazineHCID 19423693HCID 19423693, compound

Product 1

HCID 54466270(RS)-1-ethyl-7-fluoro-8-[3-(3-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acidYield 87.3%

Procedure

Working under the conditions of Example 16, but starting with 1-ethyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.5 g) and (RS)-2-(3-fluorophenyl)piperazine (1.98 g), (RS)-1-ethyl-7-fluoro-8-[3-(3-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid (2 g) is obtained in the form of a yellow solid, m.p. 284° C.

Sources & evidence

ORD record
ord-a1816d033f0f4828bfbca8f12ab25589
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

Loading…