Sulfuric Acid → HCID 86617503, compound

Participants

Reaction Steps

A mixture of 4-chloro-3-{5-[4-(4-methoxy-benzyl)-5-methyl-4H-[1,2,4]triazol-3-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (85 mg; 0.151 mmol) (from Example 58 supra) with trifluoroacetic acid (1.0 mL; 13 mmol), anisole (100 μL; 0.92 mmol) (Aldrich) and sulfuric acid (50 μL; 0.94 mmol) was stirred at room temperature for 42 hours. The mixture was concentrated. The residue was diluted with dichloromethane and concentrated again. The residue was then diluted with dichloromethane and methanol and washed with saturated aqueous sodium bicarbonate solution and water. The aqueous phases were backwashed with a mixture of dichloromethane and methanol. The two organic phases were combined, dried over sodium sulfate and concentrated. The crude material was purified by flash chromatography (12 g column; EtOAc followed by a gradient to 60:40 EtOAc: methanol) to give 4-chloro-3-[2-methyl-5-(methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 56.3 mg, 84.20%).

Provenance & Evidence