Diisopropylethylamine → Methyl 2-((4-(4-(3-cyclobutylureido)benzoyl)piperazin-1-yl)methyl)oxazole-4-carboxylate

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Reaction Steps

To a N,N-dimethylformamide (3 mL) solution of methyl 2-(piperazin-1-yl-methyl)oxazole-4-carboxylate 2,2,2-trifluoroacetate (174 mg, 513 μmol) and 4-(3-cyclobutylureido)benzoic acid (120 mg, 513 μmol) in N,N-dimethylformamide (5 mL) was added N,N-diisopropylethylamine (357 μL, 2.05 mmol), followed by O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyl uronium hexafluorophosphate (293 mg, 770 μmol; HATU). The mixture was stirred at room temperature for 22 hours and was then concentrated under vacuum. The residue was taken up in ethyl acetate and washed with saturated aqueous ammonium chloride and brine. The organic phase was dried on magnesium sulfate, filtered and concentrated under vacuum. The crude residue was applied to a silica gel column and eluted with 25% ethyl acetate in n-hexanes to give the title compound (34 mg). MS (ESI) m/z 442.1 [M+H]+

Provenance & Evidence