Ethylamine → HCID 66549045, 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 6, 0.2 g, 0.391 mmol) in dry DMF (3 mL) was added HATU (0.223 g, 0.58 mmol), HOBt (0.06 g, 0.43 mmol), DIPEA (0.102 g, 0.79 mmol) and 2M solution of ethyl amine in THF (2 mL) at 0° C. 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), extracted with EtOAc (2×30 mL). Combined organic layer was washed with brine (2×20 mL), saturated solution of lithium chloride (2×20 mL), water (20 mL), dried over sodium sulphate and evaporated in vacuo to get crude. Crude was purified by column chromatography on silica gel (100-200 mesh size). Compound was eluted using 1% methanol in DCM to afford off white solid (0.20 g, 64%). 1H-NMR (400 MHz, CDCl3) δ: 1.15 (t, 3H, J=7.28 Hz), 2.67-2.78 (m, 2H), 2.84-2.96 (m, 2H), 3.22-3.26 (m, 1H), 3.28-3.35 (m, 2H), 3.67 (d, 1H, J=17.24 Hz), 4.07 (d, 1H, J=17.2 Hz), 5.43 (bs, 1H), 7.56 (d, 2H, J=8.36 Hz), 7.64-7.66 (m, 4H); LC-MS (m/z): [M−H] 535.00.

Provenance & Evidence