4-(Piperazin-2-YL)benzonitrile → HCID 54273646, compound

HRID 344864Notes

Reaction equation

HRID 344864 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.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:35][NH:34][CH2:33][CH2:32][NH:31]2)=[CH:26][CH:25]=1)#[N:23]>C(N(CC)CC)C>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([CH:30]2[NH:31][CH2:32][CH2:33][N:34]([C:2]3[C:3]([F:21])=[CH:4][C:5]4[C:6]([CH:20]=3)=[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]=4)[CH2:35]2)=[CH:28][CH:29]=1)#[N:23]

Participants

4

Reactant 2

HCID 46253944-(Piperazin-2-YL)benzonitrileHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 54273646HCID 54273646, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(RS)-8-[3-(4-Cyanophenyl)-1-piperazinyl]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was prepared under the conditions of Example 11, but starting with 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid (1.84 g), (RS)-2-(4-cyanophenyl)piperazine (5.61 g) and triethylamine (1.7 cc). (RS)-8-[3-(4-Cyanophenyl)-1-piperazinyl]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid (1.15 g) is obtained in the form of a yellow solid, decomposing at 332° C.

Workup

  1. custom(RS)-8-[3-(4-Cyanophenyl)-1-piperazinyl]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was prepared under the conditions of Example 11

Sources & evidence

ORD record
ord-075790bf2de641b09d3fc0f822ecd0e2
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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