1-Aminohydantoin → 1-[(E)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidine-2,4-dione

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Reaction Steps

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-aminoimidazolidine-2,4-dione (13.6 mg, 0.12 mmol) was stirred in MeOH at room temperature over a weekend. Light yellow solid was filtered to give the title compound (6 mg, 0.014 mmol). The filtrate was purified on HPLC (acidic with 0.05% TFA) to give the title compound as TFA salt (8 mg, 0.0145 mmol). The combined yield was 48%. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.46 (s, 1H), 9.02 (d, 1H), 8.55 (d, 1H), 8.48 (s, 1H), 8.46 (s, 1H), 8.18 (d, 1H), 8.0 (s, 1H), 7.98 (s, 1H), 7.65 (d, 1H), 4.54 (s, 2H), 2.24 (s, 3H). LCMS (method B): [MH]+=437.1, tR=2.06 min.

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