Diisopropylethylamine → N-((3,3-bis(fluoromethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-benzamide

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Reaction Steps

A solution of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-benzoic acid (100 mg, 0.24 mmol) and DIPEA (124 mg, 0.88 mmol) in DMF (5 mL) was stirred at rt for 5 min and then HATU (183 mg, 0.48 mmol) was added. The mixture was stirred for 10 min prior to the addition of 6-(aminomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (126 mg, 0.44 mmol). And the resulting mixture was stirred at rt overnight. It was then concentrated under vacuum, and the residue was partitioned between 1N HCl and ethyl acetate. The organic layer separated was concentrated under vacuum, and the residue was purified by prep-TLC to provide the final title product (50 mg, 33%). 1H NMR (400 MHz, CDCl3): δ 7.47 (m, 9H), 4.61 (m, 6H), 4.07 (d, 1H), 3.78 (d, 1H), 2.41 (s, 3H) ppm; HPLC purity: 100% at 220 nm and 100% at 254 nm.

Provenance & Evidence