Reacción #91866

Ecuación de reacción

diisopropylethylamine

2-amino-4,5-dichloro-3-nitropyridine

1-(4-chlorobenzyl)piperazine

→

title compound

5-Chloro-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

Disolventes

isopropanol

isopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to room temperature
2. 2
   FiltraciónThe precipitate was collected by filtration
3. 3
   Lavadowashed with isopropanol and diethyl ether

Procedimiento

To a mixture of 2-amino-4,5-dichloro-3-nitropyridine (0.152 g, 0.73 mmol) and isopropanol (22 mL) was added 1-(4-chlorobenzyl)piperazine (0.165 g, 0.78 mmol) followed by diisopropylethylamine (0.17 mL, 0.97 mmol). The reaction mixture was heated at 45° C. for 18 h, then allowed to cool to room temperature, and diluted with isopropanol (5 mL). The precipitate was collected by filtration, washed with isopropanol and diethyl ether. The title compound was thus obtained as a yellow solid (0.215 g, 77%); 1H-NMR (500 MHz, DMSO-d6) 2.48 (br s, obscured by DMSO peak, 4H, piperazine C—H), 3.06 (br t, J=4.3 Hz, 4H, piperazine C—H), 3.52 (s, 2H, NCH2C6H4Cl), 6.95 (s, 2H, NH2), 7.35 (d, J=8.5 Hz, 2H) and 7.38 (d, J=8.5 Hz, 2H) (3,5-ArH and 2,6-ArH), 8.06 (s, 1H, 6-H); LC-MS (ESI, m/z): Rt=1.70 min-382, 384, 386 [(M+H)+, Cl2 isotopic pattern].

Fuente