Hydrochloric Acid → (S)-3-(2-Ethyl-4-{5-[6-(1-ethyl-propyl)-4-methyl-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol

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Reaction Steps

2-{(R)-3-[4-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-6-(1-ethyl-propyl)-4-methyl-pyridine (42 mg) is prepared by coupling and cyclizing 6-(1-ethyl-propyl)-4-methyl-pyridine-2-carboxylic acid (67 mg, 323 μmol) with (R)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-N-hydroxy-5-methyl-benzamidine (130 mg, 420 μmol) as described in Example 1. This material is dissolved in dioxane (5 mL) and 2 M aq. HCl (1 mL) and the mixture is stirred at rt for 16 h. The mixture is concentrated and the crude product is purified on prep. TLC using DCM containing 10% of 7 N NH3 in methanol to give the title compound (25 mg) as a pale yellow glass; LC-MS**: tR=0.80 min, [M+H]+=440.27; 1H NMR (CDCl3): δ0.85 (t, J=7.3 Hz, 6H), 1.32 (t, J=7.3 Hz, 3H), 1.79 (quint, J=7.3 Hz, 4H), 2.40 (s, 3H), 2.49 (s, 3H), 2.72-2.83 (m, 4H), 3.82-4.00 (m, 5H), 4.13-4.21 (m, 1H), 7.16 (s, 1H), 7.91 (s, 1H), 7.92 (s, 1H), 8.00 (s, 1H).

Provenance & Evidence