Methanol → N-Methyl-4-[4-[2-(1-methyl-2-oxo-3,4-dihydroquinolin-5-yl)ethyl]piperazin-1-yl]benzofuran-2-carboxamide

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Reaction Steps

2-(1-Methyl-2-oxo-3,4-dihydroquinolin-5-yl)acetaldehyde (Example 1j, 0.50 g, 2.5 mmol) dissolved in dichloromethane (12 mL) was added to neat N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide (Example 1e, 0.542 g, 2.09 mmol). Methanol (2 mL) was added and the mixture was stirred at ambient temp for 20 min. Sodium triacetoxyborohydride (0.782 g, 3.69 mmol) was added and the mixture was stirred over the weekend. The mixture was diluted with dichloromethane and water. The organic phase was separated, dried over MgSO4, filtered, concentrated and purified by ISCO (0 to 8% 7 N ammonia/methanol in dichloromethane) to give of the title compound as a solid. Yield: 0.77 g, 70% 1H NMR (500 MHz, CDCl3) δ ppm 2.58-2.71 (m, 4H) 2.78 (br. s., 4H) 2.87-3.00 (m, 4H) 3.06 (d, 3H) 3.31 (br. s., 4H) 3.38 (s, 3H) 6.63 (d, 1H) 6.72 (d, 1H) 6.91 (d, 1H) 6.98 (d, 1H) 7.10 (d, 1H) 7.23 (t, 1H) 7.32 (t, 1H) 7.53 (s, 1H). MS m/z 447.2 [M+H]+.

Provenance & Evidence