Hydrochloric Acid → HCID 66548859, compound

Participants

Reaction Steps

To a stirred solution of 3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid (Preparation 7, 0.1 g, 0.195 mmol) in DMF (3 mL) was added HOBt (0.026 g, 0.195 mmol), DIPEA (0.051 g, 0.391 mmol) followed by addition of EDCl.HCl (0.056 g, 0.293 mmol) and cyclopropyl amine (0.011 g, 0.195 mmol) at room temperature. Resulting reaction mixture was stirred at room temperature for 18 hours under nitrogen atmosphere. After complete consumption of starting material, reaction mixture was quenched with water (20 mL) and extracted with EtOAc (5×20 mL). Combined organic layer was washed with saturated water (100 mL), brine (100 mL), dried over sodium sulphate and evaporated in vacuo to get a yellow semisolid (0.108 g, crude). Crude was purified by column chromatography on silica gel (100-200 mesh). Compound was eluted using 0.5% methanol in DCM to afford off white solid (0.020 g, 19%, CR963-125249-74-1). 1H-NMR (400 MHz, CDCl3) δ: 0.49-0.51 (m, 2H), 0.76-0.81 (m, 2H), 2.52-2.58 (m, 1H), 2.67-2.76 (m, 3H), 2.93-3.06 (m, 2H), 3.68 (d, 1H, J=17.04 Hz), 4.08 (d, 1H, J=17.16 Hz), 5.55 (bs, 1H), 7.51 (d, 2H, J=8.08 Hz), 7.63 (s, 2H), 7.68 (d, 2H, J=8.20 Hz); LC-MS (m/z): [M−H] 546.80.

Provenance & Evidence