1,2-Dichloroethane → N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-3-(5-methylpyridin-2-yl)-5-(1,3-oxazol-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of hydrochloride salt of 3-(5-methylpyridin-2-yl)-5-(1,3-oxazol-2-yl)benzoic acid (103 mg, 0.292 mmol) in N,N-dimethylformamide (4 mL) were added (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine hydrochloride salt (72 mg, 0.437 mmol), EDC (168 mg, 0.875 mmol), HOBT (134 mg, 0.875 mmol) and N,N-diisopropylethylamine (204 μL, 1.17 mmol). The reaction mixture was stirred at 20° C. for 16 h. The mixture was purified by reverse-phase HPLC gave the hydrochloride salt of the title compound (125 mg). HRMS 390.1560 (M+1). 1H NMR (500 MHz, CD3OD): δ 8.82-8.78 (m, 2H); 8.74 (t, J=1.7 Hz, 1H); 8.61 (d, J=8.2 Hz, 1H); 8.52 (s, 1H); 8.42 (d, J=8.3 Hz, 1H); 8.13 (d, J=0.9 Hz, 1H); 7.43 (d, J=0.8 Hz, 1H); 5.50 (q, J=7.2 Hz, 1H); 2.65 (s, 3H); 2.39-2.35 (m, 3H); 1.75 (d, J=7.2 Hz, 3 H).

Provenance & Evidence