Ethanol → HCID 136409082, compound

Participants

Reaction Steps

A 25 mL round-bottomed flask containing a solution of 3-(4-amino-phenyl)-1,2,4-oxadiazol-5(4H)-one 2,2,2-trifluoroacetate (0.107 g, 0.367 mmol) and CDI (0.140 g, 0.863 mmol) in anhydrous DCM (3.5 mL) was treated with DIPEA (0.200 mL, 1.150 mmol) and stirred for 3.5 h at rt. A solution of(S)-(4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (0.118 g, 0.368 mmol) in anhydrous DCM (3.5 mL) was added followed by DIPEA (0.200 mL, 1.150 mmol), and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with DCM (10 mL) and water (5 mL) and then absorbed onto a Varian Chem Elut (Diatomaceous Earth) cartridge. The organic filtrates were collected and concentrated to dryness. The resulting product was dissolved in DMSO/MeOH (1/1) (2.0 mL) and loaded on a Gilson HPLC system for purification using a MeCN/H2O 0.1% TFA gradient and Phenomenx Gemini Axia-5μ C-18 column (150×30 mm). The solvent was removed from the pure fractions in the GENEVAC and the residue was dried under high vacuum to yield the title compound as an amorphous off-white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.76 (s, 1H), 9.24 (s, 1H), 8.98 (d, J=3.9 Hz, 1H), 8.33-8.21 (m, 1H), 7.78-7.61 (m, 6H), 7.59-7.46 (m, 4H), 6.51 (d, J=8.4 Hz, 1H) MS (ESI pos. ion) m/z: 524.2 (M+H).

Provenance & Evidence