Piperazine → HCID 14700578, compound

HRID 1084379Notes

Reaction equation

HRID 1084379 reaction equation
Cl[C:2]1[C:3]([F:24])=[CH:4][C:5]2[C:6]([CH:23]=1)=[N:7][C:8]1[N:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>N1C=CC=CC=1>[F:24][C:3]1[C:2]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:23][C:6]2=[N:7][C:8]3[N:9]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 14700557HCID 14700557, compound

Product 1

HCID 14700578HCID 14700578, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Fluoro-4-oxo-8-(1-piperazinyl)-1-tert.-butyl-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Example 5 but starting from 1.7 g of 8-chloro-7-fluoro-4-oxo-1-tert.-butyl-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid and 4.3 g of piperazine in 20 cm3 of pyridine. The pure product is obtained after a single recrystallization from 20 cm3 of dimethylformamide. 1.25 g of 7-fluoro-4-oxo-8-(1-piperazinyl)-1-tert.-butyl-1,4-dihydro-benzo[b][1,8]naphthyridine-3 -carboxylic acid are isolated in the form of a yellow solid melting at 290° C., solvated by 4.5% of water.

Workup

  1. custom7-Fluoro-4-oxo-8-(1-piperazinyl)-1-tert.-butyl-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Example 5
  2. customThe pure product is obtained
  3. customafter a single recrystallization from 20 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-d4195697dedd46c8b0ebe682ffc34834
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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