1,2-Dichloroethane → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-isopropyl-5-(5-methylpyridin-2-yl)benzoic acid (100 mg, 0.392 mmol) in N,N-dimethylformamide (3.0 mL) was added the hydrochloride salt of (1S)-1-(4H-1,2,4-triazol-3-yl)ethanamine (107 mg, 0.578 mmol), EDC (90.0 mg, 0.470 mmol), HOBT (60.0 mg, 0.392 mmol) and triethylamine (0.164 mL, 1.175 mmol) and the mixture was heated to 45° C. After 1 h, water and trifluoroacetic acid were added. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrochloric acid in diethyl ether gave the title compound as a hydrochloride salt (153 mg). HRMS 350.1976 (M+1). 1H NMR (500 MHz, CD3OD): δ 9.21 (s, 1H); 8.73 (s, 1H); 8.55 (d, J=8.4 Hz, 1H); 8.36 (d, J=8.4 Hz, 1H); 8.30 (s, 1H); 8.12 (s, 1H); 8.01 (s, 1H); 5.52 (q, J=7.1 Hz, 1H); 3.20-3.12 (m, 1H); 2.63 (s, 3H); 1.79 (d, J=7.1 Hz, 3H); 1.39 (d, J=6.9 Hz, 6H).

Provenance & Evidence