Hydrochloric Acid → 2-(4-Chloro-phenyl)-6-[3-methoxy-4-(3-methyl-3h-imidazol-4-ylmethoxy)-phenyl]-6h-thieno[2,3-c]pyridin-7-one, hydrochloride

Participants

Reaction Conditions

Reaction Steps

Dissolve 2-(4-chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-3a,7a-dihydro-6H-thieno[2,3-c]pyridin-7-one (0.271 g, 0.71 mmol) in NMP (10 mL) and treat with K2CO3 (0.39 g, 2.83 mmol), and 5-chloromethyl-1-methyl-1H-imidazole hydrochloride salt (123 mg, 0.74 mmol). Stir the mixture at 80° C. overnight. Dilute the reaction with EtOAc (100 mL), wash with water (3×25 mL), dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography, eluting with 1% NH3—H2O, 30% CH3OH/EtOAc to give 0.105 g. Dissolve the material in CHCl3 (5 mL) and CH3OH (2 mL). Add 1.0 M HCl in EtOH (213 μL) stir. Concentrate and dry in vacuo to give 0.104 g (28%) of the title compound. LC-MS/ES m/z (37Cl) 479.0 [M+]. 1H NMR (DMSO-d6) δ 3.79 (s, 3H), 3.92 (s, 3H), 5.30 (s, 2H), 6.83 (d, J=7.2 Hz, 1H), 7.03 (dd, J=8.3, 2.1 Hz, 1H), 7.17 (d, J=2.1 Hz, 1H), 7.30 (d, J=8.7 Hz, 1H), 7.5 (d, J=7.2 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.83 (d, J=8.5 Hz, 2H), 7.88 (s, 3H), 9.07 (bs, 1H).

Provenance & Evidence