1-Aminoimidazolidin-2-one → 1-[(E)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidin-2-one

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A solution of 1-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (20 mg, 0.059 mmol) and 1-aminoimidazolidin-2-one (12 mg, 0.12 mmol) in MeOH was stirred at room temperature for overnight. Solvent was evaporated and the crude product was purified on flash chromatography (CH2Cl2:MeOH 9:1) to give the title compound as a white solid (8 mg, 32%). 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.98 (s, 1H), 8.52 (d, 1H), 8.43 (s, 1H), 8.26 (d, 2H), 8.19 (m, 1H), 8.06 (d, 1H), 7.66 (d, 1H), 3.55 (t, 2H), 3.38 (t, 2H), 2.30 (s, 3H). LCMS (method A): [MH]+=423.0, tR=4.63 min.

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