Ethanolamine → HCID 86663499, compound

Participants

Reaction Steps

To a solution of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-1-naphthoic acid (Preparation 7, 1 g, 2.1 mmol) in DMF (35 mL) was added HATU (970 mg, 2.5 mmol) and triethylamine (1.0 mL, 7.0 mmol). The reaction was stirred at room temperature for 15 minutes then treated with 2-amino-ethanol (145 mg, 2.4 mmol). The reaction was stirred at room temperature for 2 hours. Next, the reaction was diluted with 0.1N NaOH and extracted with EtOAc (2×150 mL). The combined organic phase was dried (Na2SO4) and concentrated under vacuum. The crude material was chromatographed (80 g Redi-Sep column) eluting from 100% heptane to 40:60 EtOAc:heptane to afford the intermediate (734 mg, 67%) as a solid. 1HNMR (CDCl3) δ ppm: 8.82 (1H), 8.33 (1H), 7.76-7.60 (5H), 7.50 (1H), 6.51 (1H) 4.28 (1H), 3.94-3.83 (3H), 3.76 (2H), 2.35 (1H); m/z (Cl) 515 [M+H]+.

Provenance & Evidence