Hydrochloric Acid → (+/-)-2-(1-Amino-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (120 mg, 0.218 mmol) in dioxane (1 mL) was added 4M HCl in dioxane (2.2 mL, 8.72 mmol) and the mixture was stirred at 60° C. After 2 hours the reaction was cooled in an ice bath and quenched with 30% aq. NH4OH (2.18 mL). Water was added, the layers were separated and the aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc:Heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.92 (br. s., 1H) 8.29 (dd, J=1.39, 0.88 Hz, 1H) 7.72-7.85 (m, 2H) 7.28 (t, J=2.84 Hz, 1H) 7.05-7.16 (m, 1H) 6.64 (s, 1H) 3.19 (s, 3H) 2.59 (br. s., 2H) 2.43 (s, 3H) 1.90 (s, 3H). HRMS calcd. for C20H18N4O2 (M+H)+ 347.1503. found 347.1486.

Provenance & Evidence