HCID 59436032, compound → HCID 25226757, compound

Participants

Reaction Steps

A solution of 5-[(4-acetyl-2,6-dichlorophenyl)amino]-9-[2-(1-hydroxy-1-methylethyl)-1,3-thiazol-4-yl]benzo[c]-2,6-naphthyridin-1(2H)-one (75 mg, 0.14 mmol) in THF (2 mL) was cooled to −10° C. and methyl magnesium bromide (0.79 mL, 1.11 mmol, 1.4 M in toluene/THF) was added. The reaction was stirred rapidly keeping the temperature between −5 & 0° C. for 1 h. After warming to room temperature, the reaction was quenched with water, diluted with ethyl acetate/THF (1:3), and extracted with water. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with methanol in dichloromethane followed by reverse phase HPLC to afford the title compound.

Provenance & Evidence