1,2-Dichloroethane → HCID 66895517, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(5-methylpyridin-2-yl)-5-[(5S)-5-pyridin-2-yl-4,5-dihydroisoxazol-3-yl]benzoic acid (11.7 g, 27.1 mmol) in N,N-dimethylformamide (150 mL) were added (1R)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride salt (7.5 g, 35.2 mmol), EDC (7.78 g, 40.6 mmol), HOAT (1.84 g, 13.5 mmol) and triethylamine (26.4 mL, 189 mmol). The reaction mixture was heated to 50° C. After 2 h, the mixture was cooled to ambient temperature and water was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane—*40% dichloromethane/acetone) gave the title compound (10.67 g). HRMS 482.1999 (M+1). NMR (400 MHz, CDCl3): δ 8.57 (ddd, J=4.8, 1.8, 1.0 Hz, 1H); 8.49 (d, J=2.1 Hz, 1H); 8.45-8.39 (m, 3H); 8.16 (t, J=1.6 Hz, 1H); 7.71-7.66 (m, 2H); 7.59-7.52 (m, 3H); 7.37 (td, J=8.3, 2.8 Hz, 1H); 7.30 (dd, J=8.6, 4.4 Hz, 1H); 7.21 (ddd, J=7.6, 4.9, 1.2 Hz, 1H); 5.87 (dd, J=10.7, 7.1 Hz, 1H); 5.41-5.31 (m, 1H); 3.92-3.78 (m, 2H); 2.36 (s, 3H); 1.55 (d, J=6.8 Hz, 3H).

Provenance & Evidence