1-(4-Fluorobenzyl)piperazine → 1-Ethyl-7-fluoro-8-[4-(4-fluorobenzyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 1266168Notes

Reaction equation

HRID 1266168 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:36]=[CH:35][C:27]([CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:26][CH:25]=1>>[CH2:19]([N:9]1[C:8]2[N:7]=[C:6]3[CH:21]=[C:2]([N:32]4[CH2:31][CH2:30][N:29]([CH2:28][C:27]5[CH:35]=[CH:36][C:24]([F:23])=[CH:25][CH:26]=5)[CH2:34][CH2:33]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

3

Reactant 2

HCID 7965631-(4-Fluorobenzyl)piperazineHCID 147005558-Chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 185491601-Ethyl-7-fluoro-8-[4-(4-fluorobenzyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 58.6%

Procedure

1-Ethyl-7-fluoro-8-[4-(4-fluorobenzyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 2, LAW OFFICES but from 1.6 g of 8-chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 3.9 g of 4-(4-fluorobenzyl)piperazine. After recrystallizing twice from 20 cm3 of dimethylformamide on each occasion, 1.4 g of 1-ethyl-7-fluoro-8-[4-(4-fluorobenzyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid were obtained in the form of a yellow solid melting at about 286-8° C.

Workup

  1. customAfter recrystallizing twice from 20 cm3 of dimethylformamide on each occasion

Sources & evidence

ORD record
ord-41b31926817a49daba19911b1990982a
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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