Ethanol → HCID 178436053, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-3-nitro-4-[4-(1-phenyl-ethyl)-piperazin-1-yl]-pyridin-2-ylamine (0.036 g, 0.09 mmol) and EtOH (4.5 ml) was added 4-(4-hydroxy-piperidin-1-yl)-benzaldehyde (0.025 g, 0.12 mmol) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.38 ml, 0.38 mmol). The reaction mixture was stirred at 80° C. for 22 h, then allowed to cool to room temperature, and concentrated in vacuo. The residue was absorbed on silica gel, the free-running powder was placed on a 10 g isolute silica column and elution with a gradient of methanol (0 to 5%) in ethyl acetate/dichloromethane (v:v; 1:1) afforded a yellow solid. The title compound was obtained as a white solid after trituration with diethyl ether (0.016 g, 32%); 1H-NMR (500 MHz, DMSO-d6) 1.35 (d, J=6.7 Hz, 3H, CHCH3), 1.45 (m, 2H) and 1.82 (m, 2H) (piperidine CH2), 2.54 (m, 2H), 2.62 (br s, 2H), 2.98 (t, 2H) and 3.70 (m, 3H) (piperazine N—(CH2)2, piperidine CH2 and piperidine CHOH), 3.50 (q, J=6.7 Hz, 1H, CHCH3), 3.67 (br s, 4H, piperazine N(CH2)2), 4.67 (d, J=4.1 Hz, CHOH, exchangeable with D2O), 7.03 (d, J=8.9 Hz, 2H) and 8.00 (d, J=8.8 Hz, 2H) (3,5-C6H4—N and 2,6-C6H4—N), 8.14 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.16 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z): Rt=3.39 min—561, 563 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 561.1975, calculated for C29H34BrN6O (M+H)+: 561.1977.

Provenance & Evidence