Nicotinic Acid → N-[7-methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide

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Reaction Steps

7-Methoxy-8-(3-morpholin-4-ylpropoxy)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Step 5, 1.0 g, 2.2 mmol) was dissolved in DMF (15 mL), and nicotinic acid (0.44 g, 3.3 mmol) was added. PyBOP (1.73 g, 3.3 mmol) and diisopropylethylamine (1.6 mL, 8.9 mmol) were subsequently added, and the mixture was stirred at rt overnight. EtOAc was added, and the solids were isolated by vacuum filtration to give the title compound (0.43 g, 40%): HPLC MS RT=1.15 min, MH+=463.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 9.01 (2H, s), 8.04 (1H, d), 7.43 (1H, d), 4.54 (2H, m), 4.34 (2H, br t), 4.23 (2H, m), 4.04 (2H, m), 4.00 (3H, s), 3.65 (2H, br t), 3.52 (2H, m), 3.31 (2H, m), 3.18 (2H, m), 2.25 (2H, m).

Provenance & Evidence