Acetic Acid → HCID 89533488, compound

Participants

Reaction Steps

To a mixture of 5-[(2-Oxopiperazin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (40 mg, 0.15 mmol), NaBH3CN (19 mg, 0.30 mmol) and HOAc (18 mg, 0.298 mmol) in 20 mL MeOH was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (52 mg, 0.30 mmol) and the mixture was stirred at RT overnight. Then saturated Na2CO3 (50 mL) was added and stirred for 30 min and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by prep-TLC to give the desired product. 1H-NMR (400 MHz, MeOD) δ ppm 7.78 (d, J=7.8 Hz, 1H), 7.39˜7.51 (m, 4H), 7.31 (d, J=7.8 Hz, 1H), 5.34 (s, 2H), 3.74˜3.80 (m, 1H), 3.32˜3.43 (m, 3H), 3.25˜3.28 (m, 1H), 3.21 (s, 2H), 2.97˜3.01 (m, 2H), 2.74˜2.84 (m, 6H), 1.89˜1.96 (m, 1H), 1.71˜1.79 (m, 3H).

Provenance & Evidence