Hydrochloric Acid → HCID 136338253, compound

Participants

Reaction Steps

To a solution of tert-butyl (1-(5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-4-yl)carbamate (80 mg, 0.15 mmol) in MeOH (1 mL) was added HCl in MeOH (2 mL) and the reaction was stirred for 4 h at RT. The suspension was filtered and the filtrate was washed with Et2O and basified with saturated NaHCO3 solution. The mixture was extracted in EtOAc (2×3 mL). The combined organic layer were dried over anhydrous Na2SO4, filtered and concentrated. The residue was triturated with 10% EtOAc in petroleum ether to give 1-(5-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-4-amine (20 mg, 31.2%) as a solid. MS (ESI, pos. ion) m/z: 420.3 (M+1); 1H NMR (400 MHz, DMSO-d6): δ ppm 8.73 (s, 1H), 7.96-8.13 (m, 3H), 7.63 (d, J=7.6 Hz, 1H), 5.42 (brs, 1H), 3.90 (d, J=10.8 Hz, 3H), 3.13-3.18 (m, 2H), 2.80 (brs, 2H), 1.82 (d, J=10.4 Hz, 3H), 1.23-1.50 (s, 8H).

Provenance & Evidence