1,4-Dioxane → HCID 86681631, compound

Participants

Reaction Steps

To a solution of (S)-4-(2-(2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (420 mg, 0.545 mmol) in DCM (10 ml), 4M HCl in dioxane (1.363 ml, 5.45 mmol) was added, and the mixture was stirred at room temperature overnight. The solvent was evaporated and the resulting crude was purified by HPLC preparative (Method 3) recovering (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-(methylsulfonamido)-1H-indol-1-yl)acetoxy)ethyl)pyridine 1-oxide (180 mg, 0.268 mmol, 49% yield). MS/ESI+ 670.09 [MH]+; [αD]=−14.56, c=0.5 in DCM; 1H NMR (300 MHz, DMSO-d6) δ ppm 9.51 (s, 1H) 8.52 (s, 2H) 7.24 (d, 1H) 7.16 (d, 1H) 6.96-7.12 (m, 4H) 6.92 (dd, 1H) 7.06 (t, 1H) 6.76 (d, 1H) 6.02 (dd, 1H) 5.22 (d, 1H) 5.05 (d, 1H) 3.89 (d, 2H) 3.41 (dd, 1H) 3.21 (dd, 1H) 2.95 (s, 3H) 1.10-1.33 (m, 1H) 0.51-0.69 (m, 2H) 0.27-0.44 (m, 2H).

Provenance & Evidence