Methanol → HCID 86701163, compound

HRID 1396678Notes

Reaction equation

HRID 1396678 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][C:23]=3[CH2:24][O:25][CH3:26])[N:20]3[C:27]([CH:30]5[CH2:34][CH2:33][O:32][CH2:31]5)=[N:28][CH:29]=[C:19]3[C:18](=[O:35])[NH:17]4)=[O:13])[C:6]2=[CH:7][N:8]=1.CO.C(OCC)(=O)C.[ClH:44]>O1CCCC1>[ClH:44].[ClH:44].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][C:23]=3[CH2:24][O:25][CH3:26])[N:20]3[C:27]([CH:30]5[CH2:34][CH2:33][O:32][CH2:31]5)=[N:28][CH:29]=[C:19]3[C:18](=[O:35])[NH:17]4)=[O:13])[C:6]2=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 56928499HCID 56928499, compound

Product 1

HCID 86701163HCID 86701163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customThe solvent was evaporated under reduced pressure, to the obtained residue
  2. additionwas added 2 mL of diethyl ether
  3. stirringthe suspension was stirred for 30 minutes
  4. filtrationThe solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-4eb51a607fb34cacb1539fd46795a35a
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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