Sodium Dithionite → 2-(4-(2,3-Diamino-5-bromopyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[4-(2-amino-5-bromo-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide (0.200 g, 0.47 mmol), ethanol (6 ml), and 1M aqueous Na2S2O4 (1.8 ml) was stirred at 80° C. for 16 h. The reaction mixture was then allowed to cool to room temperature; the solvents were removed in vacuo, and the residue was absorbed on a silica gel. The free-running powder was placed on a 10 g isolute silica column, and elution of the column with a gradient of methanol (0 to 3%) in ethyl acetate gave the title compound (0.104 g, 54%); 1H-NMR (250 MHz, DMSO-d6) 2.53, 2.70, 2.81, 3.50 (4×br s, 8H, piperazine N(CH2)2), 3.35 (s, 2H, NCH2CO), 4.75 (s, 2H, NH2), 5.60 (s, 2H, NH2) 7.23 (d, J=3.46 Hz, 1H, thiazole 4-H or 5-H), 7.30 (s, 1H, 6-H), 7.48 (d, J=3.48 Hz, 1H, thiazole 4-H or 5-H);

Provenance & Evidence