Ammonia → HCID 178469826, compound

Participants

Reaction Conditions

Reaction Steps

Ammonia gas was bubbled into a suspension of 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 (0.106 g; 0.24 mmol) (from Example 61 supra) in 2-propanol (20 mL) for 15-20 minutes. The mixture was then heated in a microwave reactor at 140° C. for 75 minutes. After cooling to room temperature the reaction mixture was diluted with dichloromethane (˜75 mL) and washed with water and then brine. The organic phase was dried (Na2SO4) and concentrated. The residue was triturated twice with hot dichloromethane to give 4-amino-3-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 80.4 mg) Additional product was obtained by chromatographing the mother liquors from the two triturations. (Yield 7.7 mg, overall 82.49%).

Provenance & Evidence