Acetic Acid → HCID 56970897, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottomed flask was placed 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6-dihydro-1-benzothiophen-7(4H)-one (60 mg, 0.2 mmol) and then suspended in 1,1-dimethoxy-N,N-dimethylmethanamine (3 mL, 20 mmol). The mixture was stirred for 6 h at 120° C. The mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was dissolved in acetic acid (5 mL, 90 mmol) and then was added hydrazine hydrate (100 uL, 2 mmol) and the mixture was stirred for 16 h at 50° C. The mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL) and was washed with saturated aqueous solution of NaHCO3 (50 mL), brine (50 mL), dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (24 g) column chromatography eluted with a 50% to 100% EtOAc/hexane to yield target compound as an yellow solid (72 mg), which include some impurities and further purification has been performed by preparative HPLC to yield title compound (30 mg, 50%) as an yellow solid. LCMS: (FA) ES+ 364, 366; 1H NMR (400 MHz, d6-DMSO) δ ppm 12.74 (br s, 1H), 8.50-8.52 (m, 2H), 7.58-7.59 (m, 2H), 7.55 (s, 1H), 7.40 (d, 2H), 7.25 (d, 2H), 7.18 (s, 1H), 4.40 (t, 1H), 3.13-3.19 (m, 1H), 2.93 (dd, 1H).

Provenance & Evidence