Acetic Acid → HCID 66795316, compound

Participants

Reaction Steps

Sodium cyanoborohydride (18.0 mg; 0.286 mmol) was added to a solution of 4-(5-(1-cyclohexyl-5-(methoxymethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde (95.3 mg; 0.26 mmol) and isopropylamine (44.3 μL; 0.52 mmol) in methanol (3 mL) and acetic acid (47 μL; 0.78 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and water (3 mL) was added and the product extracted into DCM (3×2 mL). The combined organic fractions were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by flash chromatography on a 12+M Biotage column, eluting with DCM containing increasing amounts of 5% methanol in DCM to give Example 121 as an off white solid. 1H NMR: (CDCl3, 400 MHz) δ 8.15-8.06 (3 H, m), 7.48 (2 H, d, J=7.8 Hz), 5.03 (2 H, s), 4.36-4.26 (1 H, m), 3.89 (2 H, s), 3.47 (3 H, m), 3.00-2.88 (1 H, m), 2.04-1.90 (6 H, m), 1.75 (1 H, d, J=12.3 Hz), 1.50-1.40 (2 H, m), 1.40-1.25 (1 H, m), 1.18 (6 H, d, J=6.4 Hz). LC/MS: 410 (M+H)+. HPLC (Method A) Rt 2.46 min (Purity: 99.0%).

Provenance & Evidence