AKOS BBS-00003073 synthesis

Yield:7190-90-1 98%

Reaction Conditions:

with hydrazine in ethanol at 80; for 3 h;

Steps:

Scheme 1. 1-(3-Methyl-[1,2,4]-triazolo-[4,3-b]-pyridazin-6-yl)-hydrazine.

A round-bottomed flask was charged with 6-chloro-3-methyl-[1,2,4]-triazolo-[4,3-b]-pyridazine (2.5 g, 0.015 mol) and ethanol (35 ml). To the result-ing solution was added the hydrazine hydrate (2.6 ml, 0.053 mol). Thereaction mixture was then heated at 80 °C for 3 h. After cooling to roomtemperature, the formed product slurry was filtered, washed with little etha-nol, and air-dried to afford 2.43 g (98%) of the desired product as a white solid.1H NMR (400 MHz, DMSO-d6):8.46(brs,1H),7.86(d,J 10 Hz; 1H), 6.78 (d,J 10 Hz; 1H), 4.28 (br s, 2H), 2.55 (s, 3H); LC-MS (ESI ) m/z: [M H]Calcd. forC6H9N6165.17 found 165.20, tR 0.17 min.

References:

Brenke, Jara K.;Popowicz, Grzegorz M.;Schorpp, Kenji;Rothenaigner, Ina;Roesner, Manfred;Meininger, Isabel;Kalinski, Cédric;Ringelstetter, Larissa;R'kyek, Omar;Vincendeau, Michelle;Plettenburg, Oliver;Sattler, Michael;Krappmann, Daniel;Hadian, Kamyar;Jürjens, Gerrit [Journal of Biological Chemistry,2018,vol. 293,# 34,p. 13191 - 13203]