Piperazine → 1-Cyclopropyl-7-fluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid dihydrate

HRID 981222Notes

Reaction equation

HRID 981222 reaction equation
Cl[C:2]1[C:3]([F:23])=[CH:4][C:5]2[C:6]([CH:22]=1)=[N:7][C:8]1[N:9]([CH:19]3[CH2:21][CH2:20]3)[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1.[OH2:15].[OH2:15].[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 147005568-Chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Product 2

HCID 147005731-Cyclopropyl-7-fluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acidHCID 679258661-Cyclopropyl-7-fluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid dihydrateYield 190.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Cyclopropyl-7-fluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Reference Example 5 but starting from 1 g of 8-chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 2.6 g of piperazine in 10 cm3 of pyridine. 0.6 g of 1-cyclopropyl-7-fluoro-4-oxo-8-(1-piperazinyl)-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid dihydrate is obtained in the form of a yellow solid melting at 342°-343° C.

Sources & evidence

ORD record
ord-fc40555437f34d9290ae651728fcfd61
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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