Triethylamine → HCID 68418947, compound

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vessel was charged with 50 mg of 4-[1-(2-Chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-ylamino]-benzenesulfonamide (0.14 mmol, 1 equiv), 110 mg (S)-3-amino-piperidine-1-carboxylic acid tert-butyl ester (0.57 mmol, 4 equiv) and 17.0 mg DMAP (0.014 mmol, 0.1 equiv) in NMP (1.5 mL). The resulting solution was warmed to 130° C. via microwave irradiation for 20 min and then heated at 180° C. for an additional 70 min via microwave irradiation. The reaction mixture was cooled and concentrated in vacuo and the residue purified by preparative HPLC. To a solution of 12.0 mg of this product, 3-(S)-{4-[3-(4-sulfamoyl-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-ylamino}-piperidine (0.029 mmol, 1 equiv) in dichloromethane (5 mL), di-tert-butyl dicarbonate (9.5 mg, 0.043 mmol, 1.5 equiv) and 6 μL triethylamine (0.058 mmol, 2 equiv) were added and the resulting solution stirred at rt for 1 h. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography on silica gel eluting with 50% EtOAc: petroleum ether moving to EtOAc (4.2 mg, 29%); MS (ES+) m/e 515.55, (ES−) m/e 513.70

Provenance & Evidence