Diisopropylethylamine → 5-Bromo-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-4-chloro-3-nitro-pyridin-2-ylamine (0.126 g, 0.50 mmol) and isopropanol (15 ml) was added 1-(4-chlorobenzyl)-piperazine (0.115 g, 0.55 mmol) followed by diisopropylethylamine (0.10 ml, 0.55 mmol). The reaction mixture was heated at 45° C. for 18 h, then allowed to cool to room temperature. The precipitate was collected by filtration and washed with isopropanol and diethyl ether. The title compound was thus obtained as a yellow solid (0.148 g, 70%); 1H-NMR (500 MHz, DMSO-d6) 3.05 (br s, 4H, piperazine N(CH2)2), 3.52 (s, 2H, NCH2), 7.02 (s, 2H, NH2), 7.34 (d, J=8.52 Hz, 2H) and 7.38 (d, 2H) (3,5-ArH and 2,6-ArH), 8.16 (s, 1H, 6-H); LC (Method B)-MS (ESI, m/z): Rt=2.92 min—426, 428, 430 [(M+H)+, BrCl isotopic pattern].

Provenance & Evidence