Triethylamine → (S)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarbothioamide

Participants

Reaction Steps

EDCI (157 mg, 0.819 mmol) was added to a mixture of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid (Example 9, Step 1; 50 mg, 0.136 mmol) and HOBT-H2O (62.7 mg, 0.409 mmol) in DMF (2 mL) at ambient temperature, and the reaction mixture was stirred for 20 minutes at ambient temperature. 1.0 mL of hydrazinecarbothioamide (12.4 mg, 0.136 mmol) in DMF and triethylamine (95 μL, 0.682 mmol) were added. The resulting mixture was stirred for 1 hour at ambient temperature. The reaction mixture was diluted with EtOAc, washed with aqueous NH4Cl, NaHCO3, and brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by silica gel flash column chromatography (0-5% MeOH in dichloromethane) to afford 20.2 mg (21%) of (S)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarbothioamide. LCMS (APCI−) m/z 438.4 [M−H]+.

Provenance & Evidence