Diisopropylethylamine → N-[(2S)-3-(2-Ethyl-4-{5-[2-(1-ethyl-propyl)-6-methoxy-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide

Participants

Reaction Steps

To a solution of 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid (200 mg, 770 μmol) in DMF (3 mL) and THF (10 mL), DIPEA (200 mg, 1.54 mmol) and TBTU (272 mg, 847 μmol) are added. The mixture is stirred at rt for 10 min before N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide (251 mg, 770 μmol) is added. The mixture is stirred at rt for 30 min, diluted with EA (100 mL) and washed with brine. The org. extract is concentrated and the residue is dissolved in dioxane (50 mL). The mixture is stirred at 100° C. for 2 h before it is concentrated. The crude product is purified on prep. TLC plates using DCM containing 10% of methanol to give the title compound (180 mg) as a resin; LC-MS: tR=1.08 min, [M+H]+=513.13; 1H NMR (CDCl3): δ0.84 (t, J=7.3 Hz, 6H), 1.31 (t, J=7.5 Hz, 3H), 1.68-1.88 (m, 4H), 2.38 (s, 3H), 2.55-2.64 (m, 1H), 2.74 (q, J=7.5 Hz, 2H), 3.50-3.58 (m, 1H), 3.74-3.94 (m, 4H), 4.01 (s, 3H), 4.17-4.25 (m, 3H), 7.09 (t br, J=5.5 Hz, 1H), 7.31 (d, J=1.3 Hz, 1H), 7.43 (d, J=1.3 Hz, 1H), 7.86 (d, J=1.8 Hz), 7.88 (d, J=2.0 Hz).

Provenance & Evidence