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

HRID 344855Notes

Reaction equation

HRID 344855 reaction equation
Cl[C:2]1[C:3]([F:22])=[CH:4][C:5]2[C:6]([CH:21]=1)=[N:7][C:8]1[N:9]([CH2:19][CH3:20])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:35][NH:34][CH2:33][CH2:32][NH:31]2)=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:19]([N:9]1[C:8]2[N:7]=[C:6]3[CH:21]=[C:2]([N:34]4[CH2:33][CH2:32][NH:31][CH:30]([C:27]5[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=5)[CH2:35]4)[C:3]([F:22])=[CH:4][C:5]3=[CH:14][C:13]=2[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]1)[CH3:20]

Participants

4

Reactant 2

HCID 46176232-(4-Fluorophenyl)piperazineHCID 147005558-Chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 53824050(RS)-1-Ethyl-7-fluoro-4-oxo-8-[3-(4-fluorophenyl)-1-piperazinyl]-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 42.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The reaction is performed under the conditions of Example 4, but starting with 8-chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8 ]-naphthyridine-3-carboxylic acid (1.5 g) and (RS)-2-(4-fluorophenyl)piperazine (3.4 g) in pyridine (15 cc). (RS)-1-Ethyl-7-fluoro-4-oxo-8-[3-(4-fluorophenyl)-1-piperazinyl]-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (0.92 g) is obtained in the form of a yellow solid, m.p. 298° C.

Sources & evidence

ORD record
ord-c58e21139aa048aead8f63054985faa1
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

Loading…