Hydrochloric Acid → HCID 51347188, compound

Participants

Reaction Steps

To a solution of 2-phenyl-1-(tetrahydrofuran-3-yl)ethanone (Intermediate 92) (60 mg, 0.32 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (67.5 mg, 0.32 mmol) and urea (57.4 mg, 0.96 mmol) in 20 mL of ethanol was added 0.2 mL of conc. HCl, and the mixture was refluxed for 2 days. The solvent was removed under reduced pressure, and the residue was purified by reverse-phase preparatory HPLC (26-53% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 15 min.) to give Compound 173 (26 mg, yield 20.0%). 1H NMR (DMSO-d6 400 MHz): δ 10.25 (s, 1H), 8.05 (m, 1H), 7.42 (d, J=7.2 Hz, 1H), 7.28 (m, 4H), 7.08 (d, J=7.2 Hz, 2H), 6.95 (d, J=18.8, 1H), 5.08 (m, 1H), 3.98 (m, 3H), 3.62 (m, 3H), 3.01 (m, 1H), 2.13 (m, 2H), 1.31 (m, 3H); MS (ESI): m/z 426.2 [M+1]+.

Provenance & Evidence