Water → Ethyl 3-((5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)amino)-3-oxopropanoate

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Reaction Steps

2-(5-Aminopyridin-3-yl)-N-benzyl-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.500 g, 1.27 mmol) was dissolved in CH2Cl2 (10 mL) and pyridine (0.103 mL, 1.27 mmol) was added, followed by the addition of ethyl 3-chloro-3-oxopropanoate (0.192 g, 1.27 mmol). The reaction mixture was stirred at room temperature for 14 h. Water (10 mL) was added to the reaction mixture followed by addition of CH2Cl2 (10×4 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 3% methanol in CH2Cl2) to afford ethyl 3-((5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)amino)-3-oxopropanoate (0.400 g, 62.0%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=7.2 Hz, 3H), 3.54 (s, 2H), 4.15 (q, J=7.2 Hz, 2H), 4.82 (d, J=5.6 Hz, 2H), 6.66 (t, J=5.6 Hz, 1H), 6.81 (d, J=2.8 Hz, 1H), 7.27-7.55 (m, 10H), 7.91 (d, J=2.8 Hz, 1H), 8.81 (d, J=2.4 Hz, 1H), 8.87 (dd, J=2.4 Hz, J=1.6 Hz, 1H), 9.09 (d, J=1.6 Hz, 1H), 10.52 (s, 1H). LCMS Condition B-49: retention time 1.91 min, [M+1]=507.2. HPLC Condition B-32: retention time 10.36 min, Purity 98.80%.

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