1,2-Dichloroethane → HCID 57805465, compound

Participants

Reaction Steps

To a round bottom flask was added EDC (535 mg, 2.79 mmol), HOBt (377 mg, 2.79 mmol), anhydrous DCM (17.5 mL), anhydrous NMP (.2.5 mL), and cyclopropanecarboxylic acid (248 mg, 5.40 mmol). The reaction mixture was then stirred at room temperature under an atmosphere of nitrogen for 30 minutes. Then added tert-butyl {1-[4-(5-hydrazino-3-phenyl-1,6-naphthyridin-2-yl)phenyl]cyclobutyl}carbamate (1-6) (1.221 g, 2.54 mmol). The reaction mixture was then permitted to stir overnight (18 hours) at room temperature under an atmosphere of nitrogen. Acetic acid (2.178 mL, 38.0 mmol) was added and the reaction mixture was heated in a hot oil bath at 80° C. for 2 hours. The reaction mixture was permitted to cool to room temperature and ethyl acetate was added and the mixture was washed with a saturated solution of sodium bicarbonate, water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography 90% EtOAc/DCM (isocratic). The appropriate fractions were combined and the solvent was removed in vacuo to give tert-butyl {1-[4-(3-cyclopropyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclobutyl}carbamate (1-6 g) as a pink solid. HRMS (M+H)+: observed=532.2729, calculated=532.2707.

Provenance & Evidence