Triethylamine → (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

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Reaction Steps

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.1031 g, 0.5378 mmol) was added to a mixture of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid (0.075 g, 0.1793 mmol) and hydroxybenzotriazole (0.073 g, 0.5378 mmol) in DMF (0.6 mL) at ambient temperature. After stirring for 10 minutes, hydrazine monohydrate (0.02609 mL, 0.5378 mmol), followed by triethylamine (0.07496 mL, 0.5378 mmol) were added. The mixture was stirred at ambient temperature for 4 hours, diluted with EtOAc, washed with aqueous saturated NH4Cl, brine, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (2-8% MeOH in DCM) to provide (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.061 g, 79% yield) as a clear oil.

Provenance & Evidence