4-Methylpiperidine → HCID 44479846, compound

Participants

Reaction Steps

A solution of (S)-5-{[1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-amino}-5-(3-trifluoromethyl-phenyl)-pentanoic acid (60 mg, 0.13 mmol) and 4-methylpiperidine (40 mg, 0.40 mmol) in DMF (3 mL) is treated with O-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium tetrafluoroborate (TBTU) (64 mg, 0.20 mmol). The reaction mixture is stirred at room temperature for 16 hours. The crude reaction mixture is purified directly by preparative reverse phase HPLC (eluted with 10 to 90% CH3CN/H2O and 0.1% TFA as additive) to afford 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [(S)-5-(4-methyl-piperidin-1-yl)-5-oxo-1-(3-trifluoromethyl-phenyl)-pentyl]-amide (21 mg, 30% over 2 steps).

Provenance & Evidence