Triethylamine → (+/-)-2-Methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-nicotinamide

Participants

Reaction Steps

To a solution of 0.040 g (0.26 mmol) of 6-methoxy-pyridine-2-carboxylic acid dissolved in 8 mL of anhydrous dichloromethane was added 0.11 mL (0.79 mmol) of triethylamine, 0.050 g (0.26 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.035 g (0.26 mmol) of 1-hydroxybenzotriazole. The resulting mixture was stirred at room temperature for 10 min and added slowly at −10° C. to a solution of 0.110 g (0.26 mmol) of (+/−)-9-amino-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-5H-1,4a,7-triaza-benzocyclohepten-4-one dihydrobromide (2:1) dissolved in a mixture of 17 mL of anhydrous dichloromethane and 0.15 mL (1.05 mmol) of triethylamine. The resulting mixture was stirred at −10° C. for 1 hour and at room temperature for 16 hours. After addition of water, extraction with dichloromethane; the reaction mixture was washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated to dryness. The residue was chromatographed on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 90/10/1 to afford 0.100 g (90%) of the pure product as a powder.

Provenance & Evidence