Triethylamine → 1-[2-(2-Methoxy-benzylamino)-quinolin-6-yl]-3-(1-methyl-piperidin-4-yl)-urea

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Reaction Conditions

Reaction Steps

N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine (example 10, step B, 65 mg, 0.233 mmol) was dissolved in tetrahydrofuran (3 ml) and triethylamine (0.052 mL, 0.512 mmol) was added. At 0° C. bis(trichloromethyl)carbonate (31 mg, 0.105 mmol) was added and the reaction mixture subsequently heated to 80° C. for 3 h. Upon cooling to ambient temperature triethylamine (0.052 mL, 0.512 mmol) and 1-methyl-piperidin-4-ylamine (27 mg, 0.233 mmol) were added and the whole reaction mixture was stirred over night at 50° C. After evaporation of the solvent, the residue was taken up in water and extracted with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and the filtrate was evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol) and to yield the title compound as white solid (15 mg, 15%). MS: m/e=420.4 (M+H+).

Provenance & Evidence