Pyridine → 1-Acetyl-piperidine-4-carboxylic acid {4-[(S)-3-((S)-2-methyl-pyrrolidin-1-yl)-cyclopentyl]-phenyl}-amide

Participants

Reaction Steps

4-[(S)-3-((S)-2-Methyl-pyrrolidin-1-yl)-cyclopentyl]-phenylamine (Intermediate 14) was dissolved in DCE (1 mL). To this solution was transferred a solution of 1-acetyl-piperidine-4-carboxylic acid chloride in DCE (1 mL), followed by pyridine (0.5 mL). The solution was stirred at r.t. for 2 h when TLC (5% of 7N NH3 MeOH in DCM) and LC/MS showed that the reaction was complete. The reaction was quenched with polymer bound diethylenetriamine (4 mmol/g) (0.1 g) and the suspension was stirred for 30 min. Then, 10 mL of DCM was added to the suspension and the suspension was filtered through a celite pad, rinsed with DCM and 10% MeOH in DCM. The crude product was purified on a silica gel column eluted with 5% of 7N NH3 MeOH in DCM to obtain 15.9 mg (63%) of the title compound as a gummy solid.

Provenance & Evidence