4-Methylmorpholine → N-(4-tert-butyl-benzyl)-N-[2-(3,4-dichloro-phenyl)-ethyl]-5-ethyl-2-methylamino-nicotinamide

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Reaction Conditions

Reaction Steps

A mixture of 5-ethyl-2-methylamino-nicotinic acid ethyl ester (40 mg, 0.19 mmol), 2 M aq. potassium hydroxide solution (0.19 mL, 0.38 mmol) and THF was heated at 60° C. for 16 h, then evaporated to dryness. The residue was taken up in DMF (3.2 mL) and treated with (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine (71 mg, 0.21 mmol), HBTU (109 mg, 0.29 mmol), and 4-methylmorpholine (58 mg, 0.57 mmol). The homogeneous solution was stirred at RT for 16 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced the title compound (77 mg, 80%). Light yellow oil, MS (ISP) 498.4 (M+H)+.

Provenance & Evidence