Nicotinic Acid → HCID 44632659, compound

Participants

Reaction Steps

To a stirred solution of nicotinic acid (1 eq) in DMF (13 vol) was added HOBt (1.2 eq) and EDC.HCl (1.2 eq) at room temperature. To this mixture was added the free-based (using triethylamine (1.1 eq)) salt of C-[3-(3,4-dichloro-phenyl)-4,5-dihydro-isoxazol-4-yl]-methylamine hydrochloride (1 eq) in DMF (10 vol) and the reaction was stirred at room temperature for 18 hours. Water (100 vol) was added and the pH adjusted to 12 using 2N NaOH. The oily precipitation was extracted with EtOAc (2×67 vol). The organic phases were combined and washed with water (3×67 vol), brine (1×67 vol), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash column chromatography (eluent: EtOAc:heptane) to yield N-[3-(3,4-Dichloro-phenyl)-4,5-dihydro-isoxazol-4-ylmethyl]-nicotinamide.

Provenance & Evidence