Methylamine → HCID 68630541, compound

Participants

Reaction Steps

To a solution of 3-{2-ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid (40 mg 89 μmol) in DMF (5 mL), DIPEA (35 mg, 268 μmol) is added. The mixture is cooled to 0° C. before PyBOP (51 mg, 98 μmol) is added. The mixture is stirred at 0° C. for 15 min before methylamine (58 μL of a 2 M solution in THF) is added. The mixture is stirred at rt for 16 h, diluted with sat. aq. NaHCO3 solution, and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates using heptane:EA 1:4 to give the title compound (35 mg) as a white solid; LC-MS: tR=1.10 min, [M+H]+=421.25; 1H NMR (CDCl3): δ 1.00 (d, J=6.5 Hz, 6H), 1.31 (t, J=7.3 Hz, 3H), 1.89-2.00 (m, 1H), 2.34-2.41 (m, 2H), 2.44 (s, 3H), 2.47 (s, 3H), 2.63 (d, J=7.0 Hz, 2H), 2.76 (q, J=7.8 Hz, 2H), 2.85 (d, J=4.5 Hz, 3H), 3.06-3.13 (m, 2H), 5.38 (s br, 1H), 7.91 (s, 1H), 7.93 (s, 1H), 8.10 (s, 1H), 8.55 (s, 1H).

Provenance & Evidence