Hydrochloric Acid → HCID 178465659, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (Example 9, Step 2; 95 mg, 0.25 mmol) in a mixture of THF (2 mL) and DMF (1 mL) at ambient temperature was added ethyl acetimidate HCl salt (37 mg, 0.30 mmol) and triethylamine (45 μL, 0.32 mmol). The reaction mixture was stirred at 0° C. for 2 hours followed by stirring at ambient temperature for 17 hours. The mixture was poured into water, neutralized with dilute aqueous HCl, extracted with EtOAc, dried over MgSO4, and concentrated to afford 40 mg (38%) of (S)—N′-(1-imino ethyl)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide which was triturated with dichloromethane. LCMS (APCI+) m/z 422.1 [M+H]+.

Provenance & Evidence