Diisopropylethylamine → 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxamide

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Reaction Steps

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 1q (187 mg, 0.43 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (138 mg, 0.43 mmol) were dissolved in 40 mL of anhydrous dichloromethane followed by the addition of diisopropylethylamine (0.2 mL, 0.95 mmol), stirred until the solution became clear, followed by the addition of 5 mL of a solution of (cis-exo)-2-methyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-amine 5k (60 mg, 0.43 mmol) in dichloromethane, and stirred for another 2 hours. The resulting solution was added with 30 mL of dichloromethane, washed with dilute aqueous ammonia (20 mL), water (20 mL) and saturated sodium chloride solution (20 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 (cis-exo)-N-2-methyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-yl]-7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxamide 5 (170 mg, yield: 71.0%) as a white solid.

Provenance & Evidence