Hydrogen chloride-ethyl acetate → HCID 67134359, compound

HRID 1807879Notes

Reaction equation

HRID 1807879 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]1[C:23]([CH:26]3[CH2:31][CH2:30][CH2:29][O:28][CH2:27]3)=[N:24][CH:25]=[C:17]1[C:16](=[O:32])[NH:15]2)=[O:11].[ClH:33].C(OCC)(=O)C>CO.O1CCCC1>[ClH:33].[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]1[C:23]([CH:26]3[CH2:31][CH2:30][CH2:29][O:28][CH2:27]3)=[N:24][CH:25]=[C:17]1[C:16](=[O:32])[NH:15]2)=[O:11]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58575021HCID 58575021, compound

Product 1

HCID 67134359HCID 67134359, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 37 mg of (+)-7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-8-methyl-1-(tetrahydro-2H-pyran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one in 1 mL of methanol and 2 mL of tetrahydrofuran was added 32 μL of 4 M hydrogen chloride/ethyl acetate, followed by stirring at room temperature for 1 hour. The precipitated solid was collected by filtration, washed with ethyl acetate, and then dried under reduced pressure to obtain 24 mg (>99% ee) of (+)-7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-8-methyl-1-(tetrahydro-2H-pyran-3-yl)imidazo[1,5-a]quinoxalin-4(5H)-one hydrochloride as a white solid.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with ethyl acetate
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-81acc288d17a49fc9d81c8a7f66160c3
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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