Methanol → HCID 86701163, compound

Participants

Reaction Steps

373 mg of 7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one was purified by preparative HPLC (flow rate: 8 mL/min, acetonitrile/water=30/70) using CHIRALCEL (registered trademark) OJ-RH column, 5 μm, 20×150 mm (Daicel Chemical Industries, Ltd.). As a compound with a short retention time (retention time: 9.32 min), 125 mg of (−)-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one was obtained, and as a compound with a long retention time (retention time: 13.31 min), 132 mg of (+)-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one was obtained. To a mixture of 125 mg of (−)-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one, which was a compound with a short retention time, 5 mL of methanol and 7.4 mL of tetrahydrofuran was added 230 μL of a 4 M hydrogen chloride-ethyl acetate solution, followed by stirring at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, to the obtained residue was added 2 mL of diethyl ether, and the suspension was stirred for 30 minutes. The solid was collected by filtration and dried under reduced pressure to obtain 128 mg of (−)-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one dihydrochloride, which was a compound with a short retention time, as a white solid. To a mixture of 132 mg of (+)-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one, which was a compound with a long retention time, 5 mL of methanol and 7.4 mL of tetrahydrofuran was added 243 μL of a 4 M hydrogen chloride-ethyl acetate solution, followed by stirring at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, to the obtained residue was added 2 mL of diethyl ether, and the suspension was stirred for 30 minutes. The solid was collected by filtration and dried under reduced pressure to obtain 125 mg of (+)-7-[(5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-1-yl)carbonyl]-8-(methoxymethyl)-1-(tetrahydrofuran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one dihydrochloride, which was a compound with a long retention time, as a white solid.

Provenance & Evidence