Urea → {1-[4-(3-Benzyl-ureido)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid

Participants

Reaction Steps

Urea formation: To a solution of [1-(4-amino-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester (intermediate 1.1.3, 160 mg, 0.59 mmol) in dichloromethane (2 mL) was added benzyl isocyanate (94 μL, 0.76 mmol). The reaction mixture was stirred for 1 h at room temperature. Saponification: After removing the volatiles under reduced pressure, the remaining residue was dissolved in methanol (1 mL) and treated with aqueous LiOH solution (1 M, 1.5 mL). After 18 h, the mixture was neutralized and purified via preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3).

Provenance & Evidence