Semicarbazide hydrochloride → [(E)-1-[3-(quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl]ethylideneamino]urea

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A solution of 1-(3-(quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone (40 mg, 0.132 mmol) and hydrazinecarboxamide hydrochloride (14.9 mg, 0.198 mmol) in methanol (3 mL) was stirred at 40° C. for 2 h. The solvent was removed in vacuo and the residue was purified by HPLC to afford 4.2 mg (8.8%) of the title compound as white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.45 (s, 1H), 9.24 (d, 1H), 8.91 (d, 1H), 8.86 (dd, 1H), 8.30 (d, 1H), 7.98 (d, 1H), 7.89 (s, 1H), 7.72 (dd, 1H), 7.52-7.49 (m, 2H), 6.65 (s, 2H), 4.59 (s, 2H), 2.18 (s, 3H). LCMS (method A): [MH]+=360, tR=2.95 min.

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