N-(4-Fluorophenyl)-4-piperidinamine → HCID 9912270, compound

HRID 1266163Notes

Reaction equation

HRID 1266163 reaction equation
Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:22][C:23]1[CH:35]=[CH:34][C:26]([NH:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:25][CH:24]=1>N1C=CC=CC=1>[F:21][C:3]1[C:2]([N:31]2[CH2:30][CH2:29][CH:28]([NH:27][C:26]3[CH:34]=[CH:35][C:23]([F:22])=[CH:24][CH:25]=3)[CH2:33][CH2:32]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[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 4778193N-(4-Fluorophenyl)-4-piperidinamineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 9912270HCID 9912270, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 2, but from 1.6 g of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 3.7 g of 4-(4-fluoroanilino)-piperidine in 16 cm3 of pyridine. After recrystallizing from 10 cm3 of dimethylformamide, 1.65 g of 7-fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid were obtained in the form of a yellow solid melting at about 280° C.

Workup

  1. custom7-Fluoro-8-[4-(4-fluoroanilino)piperidino]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 2
  2. customAfter recrystallizing from 10 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-4b6fcce08b7145ee96346e26c4254479
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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