Cyclohexylamine → HCID 59516070, compound

Participants

Reaction Steps

1-[4-(methoxycarbonylmethyl)phenyl]-5-propylsulfanyl-pyrazole-4-carboxylic acid (Intermediate #35) (220 mg, 0.66 mmol) was dissolved in DCM (5 mL) and 1 drop of DMF added. Oxalyl chloride (176 μL, 1.96 mmol) was added and the mixture stirred at ambient temperature for 3 h. Volatiles were removed by evaporation under reduced pressure and the resulting gum re-dissolved in DCM (2 mL) and added at ambient temperature to a solution of cyclohexylamine (66 mg, 0.66 mmol) and DIPEA (230 μL, 1.32 mmol) in DCM (5 mL). The reaction mixture was stirred at ambient temperature for 2 h, diluted with EtOAc (50 mL) and washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on to silica gel (elution gradient 0-100% EtOAc in isohexane) to afford methyl 2-[4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]phenyl]acetate as a white solid. (220 mg, 88%)

Provenance & Evidence