Dimethylacetamide → HCID 25119787, compound

Participants

Reaction Steps

To 3-(6-carboxy-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (0.095 g) in THF (6 mL) was added BOP (0.11 g), followed by DMA (0.15 mL, 2M in THF) and Hunig's Base (ethyl-diisopropylamine) (0.042 mL). Solids began to precipitate: DCM was added until all solids dissolved, and a homogenous reaction mixture was obtained. The mixture was stirred at RT for 1 h, then an additional aliquot of BOP, Hunig's base, and DMA added, and the mixture stirred at RT overnight. The product was worked up with EtOAc and H2O, washed with NaHCO3 (aq) and H2O, and dried over MgSO4. The product was concentrated, applied to a silica gel column with EtOAc, and eluted with EtOAc/MeOH, and concentrated to yield 3-(6-dimethylcarbamoyl-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 103) (80 mg) as a pale yellow solid. M+H=457; mp=235.0-236.0° C.

Provenance & Evidence