Cl.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[CH2:11][NH2:12].C(N(CC)CC)C.Cl[C:21](=[O:27])[C:22]([O:24]CC)=O.[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][NH2:37])=[N:33][CH:34]=1>C(#N)C>[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[CH2:11][NH:12][C:22](=[O:24])[C:21]([NH:37][CH2:36][CH2:35][C:32]1[CH:31]=[CH:30][C:29]([CH3:28])=[CH:34][N:33]=1)=[O:27]To a mixture of 1.8 g of (2-methoxy-4-methylphenyl)methanamine hydrochloride salt and triethylamine (5.1 mL, 3 equiv.) in dry acetonitrile (45 mL) was added ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 equiv.) dropwise at 0° C. under nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 equiv.) was added. The reaction was heated at reflux for 24 hours. After removal of the solvent, the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered, and evaporated. The residue was washed with methyl t-butyl ether (20 mL) and recrystallized from ethanol to give 1.3 g of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide as a white powder (yield 30%).
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