Acetic Acid → 1-Ethyl-7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 1266167Notes

Reaction equation

HRID 1266167 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]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.C(O)(=O)C>N1C=CC=CC=1.O>[CH2:19]([N:9]1[C:8]2[N:7]=[C:6]3[CH:21]=[C:2]([N:33]4[CH2:32][CH2:31][N:30]([C:27]5[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=5)[CH2:35][CH2:34]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

6

Reactant 3

HCID 176Acetic AcidHCID 752601-(4-Fluorophenyl)piperazineHCID 147005558-Chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 98906221-Ethyl-7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 67.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

1-Ethyl-7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 2, but from 1.75 g of 8-chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 3.6 g of 4-(4-fluorophenyl)piperazine in 18 cm3 of pyridine. The solid obtained was taken up in 10 cm3 of water and 1.9 cm3 of 10% acetic acid were added. The suspension was brought to approximately 100° C. The solidified product was filtered off and washed 2 times with 10 cm3 of water and 2 times with 10 cm3 of warm ethanol. After recrystallizing twice from 25 cm3 of dimethylformamide on each occasion, 1.7 g of 1-ethyl-7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid were obtained in the form of a pinkish-beige solid melting at about 311-312° C.

Workup

  1. custom1-Ethyl-7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 2
  2. customThe solid obtained
  3. customwas brought to approximately 100° C
  4. filtrationThe solidified product was filtered off
  5. washwashed 2 times with 10 cm3 of water and 2 times with 10 cm3 of warm ethanol
  6. customAfter recrystallizing twice from 25 cm3 of dimethylformamide on each occasion

Sources & evidence

ORD record
ord-945d0c8e609e4f60abb2ba20d3d09afd
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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