8-Chloro-2-phenyl-3-[(1S)-1-[[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]amino]ethyl]-1(2H)-isoquinolinone → HCID 178461883, compound

HRID 928538Notes

Reaction equation

HRID 928538 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([C@@H:19]([NH:21][C:22]1[N:30]=[CH:29][N:28]=[C:27]3[C:23]=1[N:24]=[CH:25][N:26]3C1CCCCO1)[CH3:20])=[CH:7]2>Cl.CCO>[N:30]1[C:22]([NH:21][C@H:19]([C:8]2[N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10](=[O:12])[C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[CH3:20])=[C:23]2[C:27]([NH:26][CH:25]=[N:24]2)=[N:28][CH:29]=1

Participants

3

Reactant 1

HCID 666077098-Chloro-2-phenyl-3-[(1S)-1-[[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]amino]ethyl]-1(2H)-isoquinolinone2×

Product 1

HCID 178461883HCID 178461883, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

8-Chloro-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-one (Compound 10) (0.42 mmol) was dissolved in HCl/EtOH (3 M, 5 mL), and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with saturated NaHCO3 aqueous solution and the pH was adjusted to about 7-8. The mixture was extracted with CH2Cl2 (50 mL×3), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was recrystallized from ethyl acetate and hexanes (1:1). The solid was collected by filtration and dried in vacuo to afford the product (S)-3-(1-(9H-purin-6-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (Formula (I)) (90% yield) as a white solid as polymorph Form A.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 aqueous solution
  2. extractionThe mixture was extracted with CH2Cl2 (50 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was recrystallized from ethyl acetate and hexanes (1:1)
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-aa9ee12865ce435281668f8414256785
Source dataset
uspto-grants-2016_03
Patent number
US09290497B2

Reaction notes

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