Triethylsilane → HCID 71559073, compound

Participants

Reaction Steps

To a mixture of 4-(2-(3-benzhydryl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)-4-methylphenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzene-sulfonamide (0.93 g, 1.11 mmol) in trifluoroacetic acid (10 mL) and triethylsilane (1.44 mL, 8.9 mmol) was added trifluoromethanesulfonic acid (0.5 mL, 5.7 mmol). The reaction mixture was heated under at reflux for 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-100% gradient of ethyl acetate in hexanes followed by trituration in methanol (3 mL) to afford 2,5-difluoro-4-(4-methyl-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a light pink solid in 22% yield (0.13 g): 1H NMR (300 MHz, DMSO-d6) δ 11.67 (s, 1H), 8.53 (s, 1H), 7.72 (dd, J=10.0, 6.4 Hz, 1H), 7.34 (d, J=1.8 Hz, 1H), 7.29 (d, J=8.9 Hz, 1H), 7.27-7.23 (m, 1H), 7.17-7.11 (m, 3H), 6.90 (dd, J=10.6, 6.5 Hz, 1H), 2.37 (s, 3H), (NH not observed); MS (ES+) m/z 516.6 (M+1).

Provenance & Evidence