Acetic Acid → HCID 68183152, compound

Participants

Reaction Steps

A solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-4,5,6,7-tetrahydro-8H-cyclohepta[b]thiophen-8-one (81.5 mg, 0.230 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.514 mL, 3.87 mmol) in tetrahydrofuran (9.27 mL, 114 mmol) was refluxed under argon for 6 hr. The reaction was cooled to room temperature and concentrated under reduced pressure. The obtained residue (81.0 mg, 0.212 mmol), (7E)-4-(4-chlorophenyl)-7-[(dimethylamino)methylene]-2-pyridin-4-yl-4,5,6,7-tetrahydro-8H-cyclohepta thiophen-8-one, was dissolved in acetic acid (6.55 mL, 115 mmol) then hydrazine hydrate (0.112 mL, 2.30 mmol) was added and the reaction mixture was heated at 50° C. for 16 h. The mixture was allowed to cool to rt and concentrated under reduced pressure. The residue was diluted with ethyl acetate (5 mL) then washed with a saturated aqueous solution of NaHCO3 (5 mL), then brine (5 mL), then dried over anhydrous MgSO4, filtered, and concentrated. The obtained residue was purified by preparative HPLC to yield 7.4 mg product as a white solid (9.0% yield). LCMS: (AA) ES+ , 378. 1H NMR (400 MHz, DMSO-d6) δ: 12.8 (br s, 1H), 8.49-8.52 (dd, J=1.7 Hz, J=4.7 Hz, 2H), 7.53-7.55 (dd, J=1.7 Hz, J=4.7 Hz, 2H), 7.34-7.39 (m, 3H), 7.04-7.08 (m, 2H), 4.65-4.70 (m, 1H), 2.63-2.75 (m, 1H), 2.20-2.32 (m, 2H), 2.0-2.10 (m, 1H).

Provenance & Evidence