Ammonia → 4-Amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Ammonia gas was bubbled into a solution of 4-chloro-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxy-methyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.12 g, 0.28 mmol) (from Example 12 supra) in 2-propanol (15 mL) for 20 minutes. The mixture was heated in a microwave reactor at 140° C. for 2 hours. The reaction mixture was concentrated. The residue was purified by flash chromatography eluting with 30% ethyl acetate in dichloromethane to give recovered staring material (25 mg) and 4-amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white powder. (Yield 0.053 g, 44%). HRMS (ES+) m/z Calcd for C21H20N4O4S+H [(M+H)+]: 425.1278. Found: 425.1274.

Provenance & Evidence