Hydrochloric Acid → HCID 66823589, compound

Participants

Reaction Steps

The products 1,1-dimethylethyl 5-[4-(bis{[(1,1-dimethylethyl)oxy]carbonyl}amino)-7-chlorofuro[3,2-c]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate (81 mg, 0.138 mmol), and 1,1-dimethylethyl 5-[7-chloro-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)furo[3,2-c]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate (33 mg, 0.068 mmol) (0.206 mmol total) were combined in DCM and concentrated to a pale yellow oil. To this oil was added 1,4-Dioxane (0.5 mL) and to the resulting solution was added HCl (4 M, dioxane) (2 mL, 8.00 mmol), and the reaction stirred overnight at room temperature. The reaction mixture was concentrated to afford crude 7-chloro-3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (81.5 mg, 0.227 mmol, 164% yield) as a beige solid. LC-MS (ES) m/z=286 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.64 (t, J=7.83 Hz, 2H), 3.09-3.19 (m, 2H), 6.83 (s, 2H), 6.90 (s, 1H), 7.32 (s, 1H), 7.46 (s, 1H). Note, NHs are not observed.

Provenance & Evidence