Methanol → HCID 67134359, compound

HRID 1189490Notes

Reaction equation

HRID 1189490 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].CO.[ClH:35].C(OCC)(=O)C>O1CCCC1>[ClH:35].[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 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 58575021HCID 58575021, compound

Product 1

HCID 67134359HCID 67134359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 34 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, 1 mL of methanol, and 2 mL of tetrahydrofuran was added 30 μL of 4 M hydrogen chloride/ethyl acetate, followed by stirring at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. The obtained residue was triturated with 1 mL of ethyl acetate to give a powder, and the suspension was stirred for 30 minutes. The solid was collected by filtration, washed with ethyl acetate, and then dried under reduced pressure to obtain 34 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. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe obtained residue was triturated with 1 mL of ethyl acetate
  3. customto give a powder
  4. stirringthe suspension was stirred for 30 minutes
  5. filtrationThe solid was collected by filtration
  6. washwashed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a3242b2dde9341c89f477a967aac4238
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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