Dimethylformamide → HCID 67829298, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 ml round bottomed flask fitted with a magnetic stirrer bar and nitrogen inlet was added 1,6-dihydro-l-[2-(3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid (0.22 g, 0.77 mmol) methylamine hydrochloride (0.104 g, 1.54 mmol), and dimethylformamide (25.5 ml). The reaction mixture was cooled in a -8° C. ice bath and treated with triethylamine (1.07 ml, 7.7 mmol) and propylphosphonic acid anhydride (0.55 ml, added as a 0.55 ml ethyl acetate solution, Angew. Chemie 1980, 92(2), 129). The flask was allowed to warm slowly to room temperature and stirred for 2.25 hours. The mixture was concentrated, slurried in aqueous sodium bicarbonate, and again concentrated. The residue was slurried in methanol and filtered. Further purification of the solid recovered from filtration via flash column chromotography (silica gel, 15-20% methanol/dichloromethane) gave the product, MP: 208°-210° C.

Provenance & Evidence