Trimethyl orthoformate → HCID 68681006, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL scintillation vial was charged with 4-tert-butyl-N-(5-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide (191 mg, 0.50 mmol), trimethyl orthoformate (0.072 mL, 0.65 mmol), AcOH (0.60 mL), and dioxane (1.5 mL). The vial was sealed, heated to 110° C., and stirred overnight. The following day, the intermediate methyl carbazate was observed at m/z 425 (via LCMS). 1-Boc-3-aminopyrrolidine (187 mg, 1.0 mmol) was subsequently added and the reaction continued at 110° C. until LCMS analysis indicated consumption of the oxadiazole intermediate. The volatiles were subsequently evacuated in vacuo and the residue was purified via reverse-phase HPLC to provide 3-{3-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-[1,2,4]triazol-4-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester as a white solid: MS (ES) M+H expected 561.1. found 561.1.

Provenance & Evidence