Tetrahydrofuran → HCID 59846230, compound

Participants

Reaction Conditions

Reaction Steps

A 2:1 mixture of 1-(6-methyl-2-phenylamino-pyridin-3-yl)-3-(6-methylsulfonyl-pyridin-3-yl)-propan-1-one and 1-(6-methyl-2-phenylamino-pyridin-3-yl)-3-(6-methylsulfinyl-pyridin-3-yl)-propan-1-one (0.22 g) was dissolved in THF (3 mL) and toluene (1.5 mL), and monomethyl oxalyl chloride (0.27 g) added. The mixture was heated to 80° C. for 2.5 h, concentrated to a semi-solid, taken up in MeOH, and K2CO3 (0.22 g) added. This mixture was heated to 80° C. for 15 min, then cooled to RT. The product was worked up in EtOAc/H2O, the organic layer washed with LiCl (2×, 0.3 wt % aq), dried over MgSO4, and purified by prep TLC (1:1 EtOAc/hexane) to provide 3-(6-methanesulfonyl-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]naphthyridine-2-carboxylic acid methyl ester (compound 92) (8 mg) as a yellow solid. M+H=464, mp=217-218° C.

Provenance & Evidence