tert-Butyl piperazine-1-carboxylate → 4-[2,6-Bis-(4-cyano-phenoxy)pyridine-3-carbonyl]-piperazine-1-carboxylic Acid tert-butyl Ester

HRID 1024685Notes

Reaction equation

HRID 1024685 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[N:16]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])=[CH:5][CH:4]=1)#[N:2].[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:10]([C:9]2[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:27][CH:26]=3)=[N:16][C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[O:11])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 676059982,6-Bis(4-cyanophenoxy)-nicotinic acid

Product 1

HCID 668182834-[2,6-Bis-(4-cyano-phenoxy)pyridine-3-carbonyl]-piperazine-1-carboxylic Acid tert-butyl EsterYield 65.2%

Procedure

Following the procedure of Example 5(c) 2,6-bis(4-cyano phenoxy)-nicotinic acid 1.25 g (3.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (0.65 g, 3.5 mmol) were used to afford 1.2 g of the required product. Percentage purity (LCMS): 95.6%, (M+1)=525.2 (with BOC). 1H NMR (DMSO-d6): δ 1.40 (9H, s), 3.30 (2H, m), 3.42 (4H, m), 3.61 (2H, m), 6.98 (1H, d), 7.35 (4H, m), 7.82 (4H, dd), 8.02 (2H, d).

Sources & evidence

ORD record
ord-9e2ed2e3164f4a5cb6be4a8f25f97f00
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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