Hydrochloric Acid → 6-[3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-(4-methoxy-phenyl)-5,6-dihydro-4h-thieno[2,3-c]pyridin-7-one, hydrochloride

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Reaction Steps

Treat 6-(4-hydroxy-3-methoxy-phenyl)-2-(4-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.12 g, 0.31 mmol) in DMF (5 mL) with 4-(2-chloro-ethyl)-morpholine hydrochloride salt (59 mg, 0.31 mmol) and 60% NaH (38 mg, 0.94 mmol). Stir the reaction at 85° C. overnight. Quench with water (5 mL) and dilute with EtOAc (150 mL). Separate the phases and wash the organic phase with water (3×50 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 1% NH3—H2O, 10% CH3OH and 90% EtOAc to give 31 mg. Dissolve the material in CH3OH (2 mL), and treat with 1.0 M HCl in EtOAc (65 μL, 0.065 mmol), with stirring at RT for 5 min. Remove the solvent in vacuo to give 33 mg (20%) of the title compound. LC-MS/ES m/z 495.0 [M+H]+.

Provenance & Evidence