Triethylamine → HCID 71576339, compound

Participants

Reaction Steps

To a solution of 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)indolizine-8-carboxylic acid (10 mg, 0.023 mmol), HATU (13 mg, 0.035 mmol) and Et3N (0.02 mL, 0.11 mmol) in DMF (5 mL) was added 6-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (10 mg, 0.046 mmol). The mixture was stirred at rt overnight. EA (40 mL) was added and the mixture was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC to give the title compound 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)indolizine-8-carboxamide (4.8 mg; yield 34%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.16 (t, J=6.0 Hz, 1H), 9.04 (s, 1H), 8.55 (s, 1H), 7.84 (s, 1H), 7.66-7.68 (m, 3H), 7.46 (d, J=7.6 Hz, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.28-7.30 (m, 2H), 7.05-7.12 (m, 2H), 4.54-4.63 (m, 4H), 1.44 (s, 6H) ppm; HPLC purity: 100.0% at 220 nm and 100.0% at 254 nm; MS: m/z=615.7 (M+1, ESI+).

Provenance & Evidence