1,4-Dioxane → HCID 71553992, compound

Participants

Reaction Steps

To a solution of (S)-4-(2-(2-(5-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (170 mg, 0.221 mmol) in DCM (10 ml), 4M HCl in dioxane (552 μl, 2.206 mmol) was added, and the mixture was reacted overnight at room temperature. The solvent was evaporated and the resulting crude was purified by preparative HPLC (Method 1) affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(5-(methylsulfonamido)-1H-indol-1-yl)acetoxy)ethyl)pyridine 1-oxide (63 mg, 0.094 mmol, 43% yield). MS/ESI+ 670.09 [MH]+, [αD]=7.68, c=0.5 in DCM. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.27 (s, 1H) 8.51 (s, 2H) 7.42 (d, 1H) 7.29 (d, 1H) 7.13-7.22 (m, 2H) 7.02 (d, 1H) 7.02 (dd, 1H) 6.91 (dd, 1H) 7.05 (t, 1H) 6.44 (dd, 1H) 6.01 (dd, 1H) 5.21 (d, 1H) 5.06 (d, 1H) 3.87 (d, 2H) 3.41 (dd, 1H) 3.21 (dd, 1H) 2.87 (s, 3H) 1.13-1.32 (m, 1H) 0.50-0.71 (m, 2H) 0.22-0.48 (m, 2H)

Provenance & Evidence