HCID 59749538, compound → HCID 11528976, compound

Participants

Reaction Steps

5-{1-[2-(4-Methoxy-benzylsulfanyl)-3H-imidazol-4-yl]-ethyl}-quinoline (Intermediate E6) (3 g, 8.0 mmol) and trifluoroacetic acid (100 mL) in a resealable tube was heated to 115° C. for 1 h 20 m. The mixture was cooled to rt and TFA removed under vacuum. The residual acid was quenched with NH3-MeOH. The residue was evaporated and resolvated with 3:1 chloroform:isopropanol (500 mL). The organic solution was washed with water (3×40 mL) and brine (1×30 mL). The solution was dried over MgSO4, filtered, and evaporated to leave a solid. This material was purified on a short column of silica gel by gradient elution with 3 to 9% NH3-MeOH:CH2Cl2 to give 4-(1-quinolin-5-yl-ethyl)-1,3-dihydro-imidazole-2-thione (Compound 7) 1.44 g (71%).

Provenance & Evidence