1-Acetylpiperazine → HCID 68717175, compound

Participants

Reaction Steps

(2R,4S)-4-[(5-Bromopyrimidin-2-yl)-(3-cyano-5-trifluoromethyl-benzyl)]amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (300 mg) is dissolved in toluene (4 ml), and thereto are added tris(dibenzylideneacetone)dipalladium (44 mg), sodium tert-butoxide (70 mg), 2-(di-tert-butylphosphino)biphenyl (58 mg) and acetyl piperazine (93 mg). The mixture is stirred at room temperature for 1 hour under nitrogen flow, then heated at 50° C. and stirred for 5.5 hours, and partitioned by adding a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer is washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; hexane:ethyl acetate=1:1→0:1) to give (2R,4S)-4-{[5-(4-acetylpiperazin-1-yl)pyrimidin-2-yl]-(3-cyano-5-trifluoromethyl-benzyl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (177 mg). MS (m/z): 667 [M+H]+.

Provenance & Evidence