Diisopropylethylamine → HCID 58576847, compound

Participants

Reaction Steps

3-{4-[4-(4-Trifluoromethyl-benzyloxy)-phenyl]-piperazin-1-yl}-propionic acid lithium salt (160 mg; 0.39 mmol, prepared in accordance with Example 37), diisopropylethyl amine (134 μL; 0.77 mmol) and tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (127 mg; 0.39 mmol) are diluted in a 2 to 1 mixture of dimethylformamide and tetrahydrofuran (1.5 mL) and the resulting solution is stirred for 5 minutes. A solution (3-methoxy-4-nitro-phenyl)-piperidin-4-yl-amine hydrochloride (100 mg; 0.35 mmol, prepared in accordance with Example 39) in dimethylformamide (0.5 mL) is added and the reaction is stirred for 3 hours at room temperature. Following dilution with dichloromethane (10 mL), the organic layer is sequentially washed with water (5 mL), aq. sat. sodium hydrogen carbonate (2×5 mL), is dried over magnesium sulfate and concentrated under reduced pressure. The residue obtained is finally purified by preparative HPLC to deliver the desired product in pure form (29.5 mg; 0.05 mmol). The structure was confirmed using Protocol II-A. Calculated mass=642; observed mass=642; HPLC retention time=3.68 min.

Provenance & Evidence