2-Dimethylaminopyridine → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[5-methyl-1-(2-oxo-2-pyrrolidin-1-yl-ethyl)-1H-pyrazol-3-yl]-benzamide

Participants

Reaction Steps

To a solution of (3-{4-chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid (41.9 mg, 0.1 mmol) in N,N-dimethylformamide (1 mL) was added a solution of 1-hydroxybenzotriazole (20.25 mg, 0.15 mmol) in N,N-dimethylformamide (0.5 mL) and carbonyldiimidazole on polystyrene (294 mg, 0.3 mmol). The mixture was shaken at room temperature for 10 minutes. Pyrrolidine (10.65 mg, 0.15 mmol) was added as a solution in N,N-dimethylformamide (1.5 mL). Polystyrene supported dimethylaminopyridine (152 mg, 0.22 mmol) was added and the mixture was shaken at room temperature for 16 h. MP-carbonate resin (139 mg, 0.4 mmol) was added and the mixture was shaken at room temperature for 3 h. The mixture was filtered, washed with methanol and concentrated in vacuo. The residue was purified by reverse phase chromatography to afford the title compound (22 mg). LCMS (m/z) 473.4 M+1.

Provenance & Evidence