Hydrochloric Acid → ethyl 4-amino-5-[4-(1H-benzimidazol-2-ylamino)phenyl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

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Reaction Steps

A solution of ethyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (50.0 mg, 0.17 mmol) and 2-chlorobenzimidazole (30.2 mg, 0.17 mmol) in n-butanol (5 mL) and DMF (1 mL) were heated (90° C.) overnight in the presence of a trace amount of 4 M hydrogen chloride in dioxane. After cooling, the solution was concentrated under reduced pressure and the residue was purified by HPLC to afford the desired product (14.2 mg, 19%). 1H-NMR (300 MHz, DMSO-d6) 8.09 (s, 1H), 8.05 (br s, 1H), 7.89 (s, 1H), 7.79-7.85 (m, 2H), 7.24-7.34 (m, 4H), 6.89-6.99 (m, 2H), 5.14 (br, s, 1H), 4.06 (q, J=7.1 Hz, 2H), 1.09 (t, J=7.1 Hz, 3H); ES-MS m/z 414.3 (MH)+; HPLC RT (Method A) 2.57 min.

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