Sodium Hydroxide → n-(4-(6h-Pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)-3-chlorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 3-chloro-N-(4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)benzenesulfonamide (0.14 g, 0.22 mmol, prepared using A from Preparation #9 and 4-(tert-butoxycarbonylamino)bicyclo-[2.2.2]octane-1-carboxylic acid [Prime Organics], C with TEA, I, and N from 3-chlorobenzenesulfonyl chloride) and 1,4-dioxane (5 mL) to give a tan suspension and then aqueous NaOH (1N, 0.45 mL, 0.45 mmol, J. T. Baker) was added. The suspension was heated at about 60° C. for about 3 h. The reaction mixture was cooled to ambient temperature and the solvents were removed under reduced pressure. Upon addition of NH4OAc (50 mM aqueous buffer solution), a solid precipitated that was collected by vacuum filtration, washed with water, and dried to give N-(4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)-3-chlorobenzenesulfonamide as a white solid (0.088 g, 86%): LC/MS (Table 2, Method a) Rt=1.88 min; MS m/z: 457 (M+H)+.

Provenance & Evidence