1,2-Dichloroethane → Hydrochloric Acid

Participants

Reaction Steps

To a solution of 2′,4′-difluoro-5-(1-hydroxy-1-methylethyl)biphenyl-3-carboxylic acid (34 mg, 0.116 mmol) in N,N-dimethylformamide (1.2 mL) was added the hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine, EDC (26.8 mg, 0.140 mmol), HOBT (17.8 mg, 0.116 mmol) and triethylamine (0.065 mL, 0.465 mmol). After 16 h, water and trifluoroacetic acid were added. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrochloric acid in diethyl ether gave the title compound as a hydrochloride salt (50.1 mg). HRMS 402.1633 (M+1). 1H NMR (500 MHz, CD3OD): δ 8.03 (t, J=1.8 Hz, 1H); 7.89-7.86 (m, 2H); 7.58 (q, J=7.6 Hz, 1H); 7.12-7.07 (m, 2H); 5.46 (q, J=7.1 Hz, 1H); 2.37 (s, 3H); 1.71 (d, J=7.1 Hz, 3H); 1.61 (s, 6H).

Provenance & Evidence