Pyridine → HCID 59437552, compound

Participants

Reaction Steps

To a reaction vessel containing N-5-cyclohexyl-[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine (69 mg, 0.3 mmol, 1 eq.) and pyridine (63 μL, 1.2 mmol, 4 eq.) in dichloromethane (1 mL) was added 4-(pyrrolidin-1-ylmethyl)benzoyl chloride hydrochloride (142 mg, 0.6 mmol, 2 eq., prepared from 4-pyrrolidin-1-ylmethyl-benzoic acid, catalytic DMF and oxalyl chloride in DCM) as a solution in dichloromethane (2 mL), dropwise. The vessel was capped and heated to reflux for approximately 16 hours. The reaction mixture was cooled and the solvent removed in vacuo. The residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a beige solid (12.4 mg, 10%). HPLC, Rt: 3.50 min (purity: 100%). LC/MS M+(ESI): 419.2, M−(ESI) 417.2.

Provenance & Evidence