Acetic Acid → HCID 178468904, compound

Participants

Reaction Conditions

Reaction Steps

To a solution (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (116 mg, 0.595 mmol) in anhydrous ethanol (5.0 mL) was added acetic acid (0.293 mL, 5.12 mmol) followed by triethylamine (0.179 mL, 1.28 mmol). Ethyl 2-(ethoxy(imino)methyl)-6-ethylisonicotinate hydrochloride (80 mg, 0.32 mmol) was added and the reaction mixture was heated to 110° C. for 30 min. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between a saturated aqueous solution of ammonium chloride (50 mL) and ethyl acetate (50 mL). The pH of the aqueous layer was adjusted to 3 using an aqueous solution of hydrochloric acid (1N). The aqueous layer was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 477.2; HPLC retention time 2.7 min (Method A).

Provenance & Evidence