Propionic Acid → HCID 178460003, compound

Participants

Reaction Steps

A mixture of propanoic acid (0.0095 mL, 0.13 mmol), HATU (0.019 g, 0.051 mmol) and N-methylmorpholine (0.014 mL, 0.13 mmol) in DCM (1 mL) was allowed to stir at rt for 30 min. Solid 4-[5-(2-chlorophenyl)-4-(4-{[2-(trimethylsilyl)ethoxy]methyl}-4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]pyridine-2-amine (0.020 g, 0.043 mmol) and DMAP (0.016 g, 0.13 mmol) were then added and the reaction mixture was allowed to stir at 80° C. overnight. The reaction mixture was allowed to cool to rt and was diluted with DCM (3 mL) and washed with saturated aqueous NaHCO3 (2 mL). The organic solution was separated and the aqueous solution was extracted with DCM. The organic solutions were combined and concentrated. The residue was redissolved in DCM (0.5 mL) and to this solution was added TFA (0.5 mL). The reaction mixture was allowed to stir at rt for 12 h and then concentrated to dryness. The residue was purified by column chromatography to give N-{4-[5-(2-chlorophenyl)-4-(4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]pyridine-2-yl}propanamide (Compound I-75) (3.5 mg, 21%). LCMS (FA): m/z=395 (M+H). 1H NMR (400 MHz, DMSO) δ 10.72 (s, 1H), 8.79 (s, 1H), 8.51 (d, J=5.2 Hz, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.67 (dd, J=5.2, 1.5 Hz, 1H), 7.64 (dd, J=8.1, 1.2 Hz, 1H), 7.58 (td, J=7.7, 1.7 Hz, 1H), 7.50 (td, J=7.5, 1.3 Hz, 1H), 2.44 (q, J=7.5 Hz, 3H), 1.08 (t, J=7.5 Hz, 3H).

Provenance & Evidence