Sodium Bicarbonate → HCID 178448144, compound

Participants

Reaction Steps

A mixture of tert-butyl 3-((4S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-2-oxoimidazolidin-1-yl)azetidine-1-carboxylate (22 mg, 0.032 mmol) and 1:2 EtOH/6N aqueous HCl (1 mL) was heated at reflux for 2 hours. After cooling, the reaction mixture was basified by slow addition of saturated aqueous NaHCO3 solution. The mixture was extracted with 10% MeOH in DCM. The combined extracts were washed with brine, dried and concentrated. The residue was purified by column chromatography (20% 7N ammonia in MeOH/dichloromethane) to give (S)-1-(azetidin-3-yl)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropylimidazolidin-2-one (12 mg, 82%) as a pale yellow solid. LCMS (APCI+) m/z 462.2 [M+H]+.

Provenance & Evidence