(S)-3-Oxiranyl-pyridine → 4-[5-(3-Cyclopentyl-propyl)-[1,2,4]oxadiazol-3-yl]-N-{4-[2-((R)-2-hydroxy-2-pyridin-3-yl-ethylamino)-ethyl]-phenyl}-benzenesulfonamide

Participants

Reaction Steps

To a solution of amine from Example 29 (0.053 g, 0.117 mmol) in dry methanol (30.0 ml) was added 3-pyridine epoxide from Example 16 (0.021 g, 0.175 mmol). The resulting solution was refluxed overnight. After concentration, the residue was purified by silica gel chromatography (13% methanol in methylene chloride) to give 0.01 g (15%) of the title compound: 1H NMR (400 MHz, CD3OD) δ8.52 (d, 1H, J=1.9 Hz), 8.42 (dd, 1H, J=1.5, 4.8 Hz), 8.13 (d, 2H, J=8.6 Hz), 7.85 (m, 3H), 7.40 (dd, 1H, J=4.8, 7.8 Hz), 7.10 (d, 1H, J=8.6 Hz), 7.03 (d, 2H, J=8.6 Hz), 4.81 (dd, 1H, J=4.9, 8.1 Hz), 2.96 (t, 2H, J=7.5 Hz), 2.93-2.70 (m, 6H), 1.90-1.72 (m, 5H), 1.68-2.48 (m, 4H), 1.42 (m, 2H), 1.11 (m, 2H).

Provenance & Evidence