Ethanolamine → N-(2-hydroxy-ethyl)-2-{4-[5-(6-isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetamide

Participants

Reaction Steps

To a solution of {4-[5-(6-isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid (50 mg, 142 μmol) in DMF (3 mL), EDC HCl (33 mg, 171 μmol), HOBt (23 mg, 171 μmol) and DIPEA (28 mg, 213 μmol) is added. The mixture is stirred at rt for 5 min before ethanolamine (10 mg, 157 μmol) is added. Stirring is continued at rt for 72 h. The mixture is diluted with EA, washed with water, and concentrated. The crude product is purified on prep. TLC plates with DCM containing 10% of MeOH to give N-(2-hydroxy-ethyl)-2-{4-[5-(6-isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetamide (26 mg) as a white solid; LC-MS: tR=0.82 min, [M+1]+=395.15; 1H NMR (CDCl3): δ1.01 (d, J=6.5 Hz, 6H), 2.19-2.29 (m, 1H), 2.46 (s, 3H), 2.53 (s br, 1H), 2.80 (d, J=7.3 Hz, 2H), 3.44 (q, J=4.8 Hz, 2H), 3.69 (s, 2H), 3.71-3.75 (m, 2H), 5.96 (s br, 1H), 7.46 (d, J=7.5 Hz, 2H), 8.18 (d, J=7.8 Hz, 2H), 8.17 (s), 8.19 (s), 8.22 (s, 1H), 9.20 (s, 1H).

Provenance & Evidence