Acetonitrile → HCID 86585292, compound

HRID 842727Notes

Reaction equation

[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7]N2C(CCl)=CN=C2)=[CH:5][CH:4]=1)#[N:2].[CH:17]([N:20]([CH:23](C)C)CC)([CH3:19])[CH3:18].[N:26]1([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(#[N:44])C>>[CH2:35]([O:34][C:32]([N:26]1[CH2:31][CH2:30][N:29]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:16][CH:15]=2)[CH:28]([CH2:18][C:17]2[NH:20][CH:23]=[N:44][CH:19]=2)[CH2:27]1)=[O:33])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 81531Diisopropylethylamine

HCID 643495Benzyl piperazine-1-carboxylate

HCID 97953581-(4-Cyanobenzyl)-5-(chloromethyl)imidazole

Product 1

HCID 86585292HCID 86585292, compound

Conditions

Temperature: 80 °C

Procedure

To an acetonitrile solution of 1-(4′-cyanobenzyl)-5-chloromethylimidazole (7.45 mmol) prepared as described in Example 1 and diisopropylethyl amine (22.4 mmol) was added 1-benzyl 1-piperazine carboxylate (10.4 mmol). This solution was stirred for 4.0 hour at 80° C. The product was isolated after silica column purification.1H-NMR (CDCl3): 7.65 (d, 2H); 7.55 (s, 1H); 7.38 (m, 5H); 7.15 (d, 2H); 7.0 (s, 1H); 5.3 (s, 2H); 5.1 (s, 1H); 3.4 (m, 4H); 3.3 (s, 2H); 2.3 (m, 4H).

Workup

customThe product was isolated
customafter silica column purification

Sources & evidence

ORD record: ord-29ca8355f5f24cc5bcc1ef16ba9cb763
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376496B1

Reaction notes

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