Sodium hydride → HCID 58742325, compound

Participants

Reaction Steps

A mixture of the compound of Example 35 (35 mg, 0.093 mmol), sodium hydride 60% (20 mg, 0.5 mmol) and 3-chloromethyl-2-methyl-pyridine hydrochloride (23 mg, 0.13 mmol) in 3 mL of dimethylformamide (DMF) was stirred overnight. Saturated aqueous ammonium chloride solution (5 mL) and water (15 mL) were added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to a oil (35 mg). The residue was purified by flash chromatography using a 50% to 80% ethyl acetate/hexanes eluant to afford 20 mg (44%) of the title compound as an oil, which was crystallized from hexanes to give a white solid. Melting point: 80–83° C. Mass spectrum: (m/e) 461(M+−H2O, +ion).

Provenance & Evidence