Diisopropylethylamine → 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-[(2S)-3-(4-methylpiperazin-1-yl)-2-hydroxy-propyl]-2,2-dimethyl-3H-benzofuran-4-carboxamide

Participants

Reaction Steps

The crude compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acid 4f (160 mg, 0.35 mmol), (2S)-1-amino-3-(4-methylpiperazin-1-yl)propan-2-ol 21c (60 mg, 0.35 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (111 mg, 0.35 mmol) and diisopropylethylamine (89 mg, 0.69 mmol) were dissolved in 25 mL of dichloromethane. The reaction solution was stirred for 2 hours. The resulting solution was added dropwise with saturated sodium bicarbonate solution to adjust pH to 8-9 and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with water (50 mL), saturated sodium chloride solution (50 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-[(2S)-3-(4-methylpiperazin-1-yl)-2-hydroxy-propyl]-2,2-dimethyl-3H-benzofuran-4-carboxamide 21 (90 mg, yield: 45.0%) as a white solid.

Provenance & Evidence