Urea → HCID 178428487, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-1-(4-amino-2-methylphenyl)-3-(3-methyl-1H-indazol-5-yl)prop-2-en-1-one (0.480 g, 1.64 mmol) in EtOH (5 mL) were added urea (0.900 g, 15 mmol) and 4N HCl/dioxane (5 mL, 20 mmol). The reaction mixture was heated to 110° C. for 17 hours, cooled down and concentrated in vacuo. The product was purified by SiO2 flash chromatography (ethyl acetate to 60:40 ethyl acetate/methanol) and preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate), followed by concentration in vacuo and lyophilization to afford the title compound as an acetate salt (58 mg, 11%). 1H NMR (400 MHz, d6-DMSO): δ 8.6 (s, 1H), 8.15 (d, 1H), 7.54 (d, 1H), 7.20 (d, 1H), 7.01 (s, 1H), 6.49 (m, 2H), 5.56 (s, 2H), 2.54 (s, 3H), 2.3 (s, 3H), 1.89 (s, 1H); MS (EI) for C19H17N5O: 332.3 (MH±).

Provenance & Evidence