Hydrochloric Acid → 4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)-2-methylbenzamide

Participants

Reaction Steps

To a solution of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (300 mg, 0.72 mmol) in acetonitrile (5 ml) at 0° C. was added Et3N (291.1 mg, 2.88 mmol), HATU (546.76 mg, 1.44 mmol) and 5-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (194.2 mg, 0.86 mmol). The reaction mixture was stirred overnight at rt. The mixture was poured into 1N HCl solution and extracted with EA (20 ml×3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC eluted with PE:EA (1:1 with 2 drops of HOAc) and prep-HPLC to give the final title compound (80 mg, yield 18.8%) as white solid: 1H NMR (300 MHz, DMSO-d6): δ 8.99 (s, 1H), 8.95 (m, 1H), 7.81-7.82 (m, 1H), 7.62-7.64 (m, 5H), 7.49-7.60 (m, 1H), 7.29-7.46 (m, 2H) 4.50-4.52 (d, J=6.0 Hz, 2H), 4.33-4.36 (m, J=9 Hz, 2H), 2.42 (s, 3H), 1.20 (s, 6H); HPLC purity: 97.1% at 214 nm and 98.3% at 254 nm; MS: 591 [M+H]+.

Provenance & Evidence