Sodium Dithionite → HCID 178432933, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chloro-4-(4-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (60.0 mg, 0.170 mmol) and 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (22.2 mg, 0.179 mmol) in EtOH (3.8 mL) was added 1M Na2S2O4 (0.678 mL, 0.678 mmol, freshly prepared) and the solution was heated to 80° C. and stirred for 16 h whilst being open to air. Once cooled, the reaction was evaporated in vacuo and the residue dry loaded onto silica. Purification was accomplished by flash chromatography on silica gel (3×14) eluting with MeOH/CH2Cl2 (5-7.5%) to yield the title compound as a pale yellow solid. Recrystallisation in EtOAc/Et2O gave the title compound (20 mg, 27%) as an off white solid. The filtrate was concentrated in vacuo, an additional amount of title compound (12 mg, 16%) as a pale yellow solid. 1H-NMR (500 MHz, CDCl3) 2.60 (s, 3H, CH3), 2.62 (s, 3H, CH3), 2.81 (app t, J=4.5 Hz, 4H, CH2), 3.76 (s, 2H, —CH2—), 3.87 (app s, 4H, CH2), 3.90 (s, 3H, NCH3), 7.77 (br s, 1H, CHar), 7.96 (br S, 1H, CHar), 12.18 (s, 1H, NH);

Provenance & Evidence