Piperazin-2-one → HCID 19025734, compound

Participants

Reaction Steps

To the resultant compound from Example 11C (320.5 mg, 0.908 mmol)in dichloromethane (5 mL) at -10° C. was added 2-oxopiperazine (140 mg, 1.40 mmol, Yu et. al. J. Med. Chem.1900, 31, 1435) in pyridine (2 mL). After 30 min at -10° C. and 30 min at ambient temperature, the solvent was evaporated and the residue was partitioned between ether and 0.5M H3PO4. The organic layer was washed with 0.5M H3PO4, saturated NaHCO3 solution and brine, and then was dried over MgSO4 and evaporated. Chromatography of the residue on silica gel with 2% methanol in chloroform afforded 237.1 mg (63%) of the desired product as a foam: TLC (5% methanol/95% chloroform) Rf =0.26; 1H NMR (CDCl3) 7.43-7.07 (m, 10H), 5.97 (br, 1H), 5.12 (d, 1 H), 5.08 (d, 1H), 3.82 (d, 1H), 3.78 (d, 1H), 3.55 (dd, 1H), 3.43-3.17 (m, 5H), 3.07 (dd, 1H), 3.01 (dd, 1H), 2.87 (dd, 1H).

Provenance & Evidence