Pyridine → HCID 23652670, compound

Participants

Reaction Steps

A mixture of 103 mg (0.42 mmol) 2-(4-cyclopentyl-piperazin-1-yl)-pyrimidin-4-ylamine (intermediate 1), 67 mg (0.428 mmol) phenyl chloroformate (commercially available) and 0.1 g (0.12 mmol) pyridine in 4 mL DCM was shaken for 30 min at room temperature. A fraction of this mixture containing 0.07 mmol of the intermediately built [2-(4-cyclopentyl-piperazin-1-yl)-pyrimidin-4-yl]-carbamic acid phenyl ester was treated with 64.8 mg (0.41 mmol) 4,4-difluoro-piperidine, hydrochloride and 0.05 mL NEt3. The mixture was shaken at room temperature and concentrated. Methanol, DMF and water were added and the mixture was subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 1.1 mg (5%) of the title compound. MS (m/e): 395.3 (MH+).

Provenance & Evidence