Diisopropylcarbodiimide → 3-[4-(2-chloro-5-fluoro-phenoxy)-piperidin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide

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Reaction Steps

To a stirred solution of 5-phenyl-pyridin-2-ylamine (0.041 g, 0.00024 mole) in THF (3 mL) was added 3-[4-(2-chloro-5-fluoro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid (0.08 g, 0.00025 mole) followed by DIC (0.036 g, 0.00028 mole). The mixture was heated to reflux for 3 hours, and then concentrated under educed pressure. The resulting residue was stirred with cold ether. The organic layers were removed by filtration and concentrated under reduced pressure to afford 0.021 g (18%) of 3-[4-(2-chloro-5-fluoro-phenoxy)-piperidin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide. LC-MS purity: 468.14 (M+1)+, 98%, 1H NMR (DMSO-d6) δ 11.2 (bs, 1H), 8.2 (t, 2H), 8.0 (d, 1H), 7.4 (m, 4H), 7.1 (t, 1H), 6.6 (d, 2H), 4.6 (s, 1H), 4.0 (d, 1H), 3.7 (m, 1H), 3.6 (m, 3H), 2.1 (bs, 9H), 1.8 (t, 4H).

Provenance & Evidence