Reaktion #60193

ord-1edb383ab3cc4fde8e34fdcb39c74736

Reaktionsgleichung

N#Cc1ccc(C(=O)CBr)cc1
4-cyanophenacyl bromide
O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+].[NH4+]
CAN
O=[N+]([O-])c1ccc(Cl)nc1
2-chloro-5-nitropyridine
Nc1nc(NCCNc2ccc(-c3ncc[nH]3)c(-c3ccc(Cl)cc3Cl)n2)ccc1[N+](=O)[O-]
{2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-imidazolyl(2-pyridyl)]amine
→
N#Cc1ccc(-c2nc(NCCNc3ccc([N+](=O)[O-])cn3)ccc2-c2ncc[nH]2)cc1
4-[3-imidazolyl-6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-2-pyridyl]Benzenecarbonitrile

Edukte

N#Cc1ccc(C(=O)CBr)cc1
4-cyanophenacyl bromide
O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+].[NH4+]
CAN
O=[N+]([O-])c1ccc(Cl)nc1
2-chloro-5-nitropyridine
Nc1nc(NCCNc2ccc(-c3ncc[nH]3)c(-c3ccc(Cl)cc3Cl)n2)ccc1[N+](=O)[O-]
{2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-imidazolyl(2-pyridyl)]amine

Reagenzien

Keine

Lösungsmittel

O
water
CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

4-[3-imidazolyl-6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-2-pyridyl]Benzenecarbonitrile was prepared from 4-cyanophenacyl bromide, CAN for the oxidation (1:1 acetic acid and water with heating at 80° C. for 1 hour), and 2-chloro-5-nitropyridine using the general method for {2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-imidazolyl(2-pyridyl)]amine.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07425557B2uspto-grants-2008_09