Diisopropylethylamine → HCID 11997367, compound

Participants

Reaction Steps

To a stirred solution of 1,4-bis(3-chloropropyl)piperazine-2,5-dione (40 mg, 0.15 mmol; prepared as described in Preparation 7) in DMF (1.5 mL) was added biphenyl-2-ylcarbamic acid piperidin-4-yl ester (44 mg, 0.15 mmol; prepared as described in Preparation 3) and DIPEA (0.078 mL, 0.45 mmol) and the reaction was allowed to stir overnight at room temperature. After overnight, 4-hydroxybenzyl amine (18.5 mg, 0.15 mmol) was added and the reaction heated to 50° C. for 16 hours. Next the reaction mixture was concentrated in vacuo and then dissolved in 1:1 mixture HOAc:H2O (1.5 mL) and purified on reverse-phase silica gel (gradient elution, 10-50% ACN/H2O) to afford the title compound in 10% yield (over 2 step) (13 mg, 0.015 mmol). MS m/z: [M+H+] calcd for C35H43N5O5, 614.4; found, 614.2).

Provenance & Evidence