Ammonia → Benzo[b]thiophene-2,7-dicarboxamide, 3-amino-4-(cyclobutyloxy)-

Participants

Reaction Steps

To a stirred solution of the above benzoic acid intermediate (2.00 g, 8.50 mmol) in THF (20 mL) was added an ammonia solution (0.5M in 1,4-dioxane, 17.0 mL, 8.50 mmol), diisopropylethylamine (3.36 g, 26.0 mmol) and PyBOP (4.43 g, 8.50 mmol). The solution was stirred at room temperature overnight then 2-mercaptoacetamide (1.1 M in MeOH, 11.6 mL, 12.76 mmol) was added and the reaction was heated at 80° C. for 3 h. Sodium ethoxide (2.68 M in EtOH, 4.80 mL, 12.86 mmol) was added and the reaction continued for 4 h. After cooling to room temperature, the reaction was diluted with 2 N sodium hydroxide solution (100 mL). The precipitate formed was collected by filtration, washed with MeOH and dried in vacuo to give 3-amino-4-cyclobutoxy-benzo[b]thiophene-2,7-dicarboxylic acid diamide (0.850 g, 2.784 mmol, 32.7%).

Provenance & Evidence