2,6-Lutidine → 4-tert-butyl-N-[5-chloro-2-(4-methyl-5-piperidin-4-yl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A 25 mL scintillation vial was charged with 4-methylcarbamoyl-piperidine-1-carboxylic acid benzyl ester (138 mg, 0.5 mmol), POCl3 (0.095 mL, 1.0 mmol), 2,6-lutidine (130 mg, 1.25 mmol), and CH3CN (1.5 mL). The vial was sealed, heated to 40° C., and stirred for four hours. The volatiles were then evacuated in vacuo and to the resultant residue was added 4-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide (193 mg, 0.5 mmol), DIPEA (0.5 mL), and dioxane (1.0 mL). The vial was sealed, heated to 130° C., and stirred for two hours. The volatiles were then removed in vacuo and to the residue was added 3 mL of 33% hydrobromic acid in acetic acid. The vial was sealed and stirred for 3 h. The volatiles were then evacuated in vacuo and the residue was purified via preparatory HPLC to afford 4-tert-butyl-N-[5-chloro-2-(4-methyl-5-piperidin-4-yl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide as a white powder: MS (ES) M+H expected 489.2, found 488.5.

Provenance & Evidence