Piperazine → HCID 67925859, compound

HRID 981214Notes

Reaction equation

HRID 981214 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.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>N1C=CC=CC=1>[CH2:19]([N:9]1[C:8]2[N:7]=[C:6]3[CH:21]=[C:2]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]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].[OH2:15].[OH2:15].[OH2:15].[CH2:19]([N:9]1[C:8]2[N:7]=[C:6]3[CH:21]=[C:2]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]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

5

Reactant 2

HCID 4837PiperazineHCID 147005558-Chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 2

HCID 14700565HCID 14700565, compoundHCID 67925859HCID 67925859, compoundYield 222%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Ethyl-7-fluoro-8-(1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Reference Example 5, but starting from 1.6 g of 8-chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 4.3 g of piperazine in 20 cm3 of pyridine. After recrystallizing 3 times from, in total, 300 cm3 of dimethylformamide, 0.94 g of 1-ethyl-7-fluoro-8-(1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid trihydrate is obtained in the form of a yellow solid melting at 320°-322° C.

Workup

  1. customAfter recrystallizing 3 times from, in total, 300 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-52e52c10a8114001b3a5d3d818e0ef11
Source dataset
uspto-grants-1991_02
Patent number
US04990515

Reaction notes

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