6-(Piperazin-1-yl)pyridine-3-carbonitrile → 2-(4-cyanobenzyl)-3-[4-(5-cyano-2-pyridyl)-1-piperazinyl]-N-(2-naphthylsulfonyl)-3-oxopropanamide

HRID 1256896Notes

Reaction equation

HRID 1256896 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][C:6]([CH2:7][CH:8]([C:16]([NH:18][S:19]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)(=[O:21])=[O:20])=[O:17])[C:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)#[N:2].[C:34]([C:36]1[CH:37]=[CH:38][C:39]([N:42]2CCNCC2)=[N:40][CH:41]=1)#[N:35]>>[C:1]([C:3]1[CH:33]=[CH:32][C:6]([CH2:7][CH:8]([C:9]([N:11]2[CH2:12][CH2:13][N:42]([C:39]3[CH:38]=[CH:37][C:36]([C:34]#[N:35])=[CH:41][N:40]=3)[CH2:15][CH2:14]2)=[O:10])[C:16]([NH:18][S:19]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)(=[O:20])=[O:21])=[O:17])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 27371846-(Piperazin-1-yl)pyridine-3-carbonitrileHCID 866452172-(4-cyanobenzyl)-N,N-diethyl-N'-(2-naphthylsulfonyl)malonamide

Product 1

HCID 685129762-(4-cyanobenzyl)-3-[4-(5-cyano-2-pyridyl)-1-piperazinyl]-N-(2-naphthylsulfonyl)-3-oxopropanamideYield 75.8%

Procedure

In the same manner as in Example 1 (4), a crude product was obtained using the compound (300 mg) obtained in Example 111 (4) and N-(5-cyano-2-pyridyl)piperazine (166 mg). This was purified by silica gel column chromatography to give the title compound (284 mg) as a white powder.

Workup

  1. customThis was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-122e439801ff4abbab4e5fdc7dd8ee1b
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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