Sodium Carbonate → HCID 178455838, compound

Participants

Reaction Steps

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 1q (200 mg, 0.46 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (147 mg, 0.46 mmol) were dissolved in 25 mL of anhydrous dichloromethane followed by the addition of diisopropylethylamine (0.2 mL, 1 mmol) and (trans)-4-(4-methylpiperazin-1-yl)cyclohexanamine 17b (90 mg, 0.46 mmol) successively. The reaction solution was stirred for 3 hours. The resulting solution was added with 20 mL of saturated sodium carbonate solution and extracted with dichloromethane (30 mL×3). The combined organic phase was washed with saturated sodium carbonate solution (30 mL×2), water (30 mL) and saturated sodium chloride solution (30 mL) successively, then dried over anhydrous sodium 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-[(trans)-4-(4-methylpiperazin-1-yl)cyclohexyl]-2,3-dihydrobenzofuran-4-carboxamide 19 (190 mg, yield: 67.0%) as a white solid.

Provenance & Evidence