Ammonia → HCID 178455830, compound

Participants

Reaction Steps

(cis)-4-[4-(Cyclopropylmethyl)piperazin-1-yl]cyclohexanamine 12e (139 mg, 0.40 mmol), 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 1q (175 mg, 0.40 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (128 mg, 0.40 mmol) and diisopropylethylamine (258 mg, 2.08 mmol) were dissolved in 50 mL of dichloromethane. The reaction solution was stirred for 2 hours followed by the addition of 50 mL of water and 10 mL of aqueous ammonia successively, and stirred for another 0.5 hours. The resulting solution was extracted with dichloromethane (50 mL×3). The combined organic phase was washed with saturated sodium chloride solution (50 mL×3), dried over anhydrous magnesium sulfate. 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-[(cis)-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexyl]-2,3-dihydrobenzofuran-4-carboxamide 12 (160 mg, yield: 61.0%) as a white solid.

Provenance & Evidence