Diisopropylethylamine → 1-Methyl-piperidine-4-carboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amide

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of 1-methyl-piperidine-4-carboxylic acid hydrochloride salt (35 mg, 179 mmol) in tetrahydrofurane (3 ml) were added at room temperature N-ethyldiisopropylamine (74 mg, 0.573 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (27 mg, 0.197 mmol), N,N-diisopropyl ethyl amine (74 mg, 0.197 mmol) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (38 mg, 0.197 mmol) and the mixture was allowed to stir for 90 min. N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine (example 10, step B, 50 mg, 0.179 mmol) was added and the reaction mixture was allowed to stir for 17 h, poured into sat. sodium bicarbonate solution (30 ml) and extracted with dichloromethane (2×30 ml). The combined organic layers were washed with water (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and crystallization (ethyl acetate/heptane) to yield the title compound as white solid (35 mg, 48%). MS: m/e=405.5 (M+H+).

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