1-Hydroxybenzotriazole → HCID 57917670, compound

Participants

Reaction Steps

To a solution of ethyl 4-(3-phenylureido)benzoate (1.00 g, 3.90 mmol) in N,N-dimethylform-amide (20 mL) was added methyl 3-(piperazin-1-ylmethyl)benzoate bis(2,2,2-trifluoroacetate) (1.25 g, 2.70 mmol), N-ethyl-N-isopropylpropan-2-amine (0.94 mL, 5.40 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (0.40 g, 2.97 mmol, HOBT) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.57 g, 2,97 mmol, EDCl). The mixture was stirred overnight at room temperature and then concentrated under vacuum. The residue was taken up in ethyl acetate and washed with water (×2) and then saturated aqueous sodium chloride. The organic phase was dried on magnesium sulfate, filtered, concentrated under vacuum. Silica chromatography (10-40% ethyl acetate in n-hexanes) and recrystallisation from methanol gave the title compound (1.02 g).

Provenance & Evidence