Sodium Bicarbonate → (S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one

HRID 1046765Notes

Reaction equation

HRID 1046765 reaction equation
[CH:1]1([N:4]2[C:13]([C@@H:14]([NH:16][C:17]3[N:25]=[CH:24][N:23]=[C:22]4[C:18]=3[N:19]=[CH:20][N:21]4C3CCCCO3)[CH3:15])=[CH:12][C:11]3[C:6](=[C:7]([CH3:32])[CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:33])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+]>Cl.CCO>[N:25]1[C:17]([NH:16][C@H:14]([C:13]2[N:4]([CH:1]3[CH2:3][CH2:2]3)[C:5](=[O:33])[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[CH3:32])[CH3:15])=[C:18]2[C:22]([NH:21][CH:20]=[N:19]2)=[N:23][CH:24]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 580089832-cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one2×

Product 1

HCID 178423765(S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-oneYield 83.2%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

2-Cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one (compound 5004) (222 mg, 0.5 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 neutralized with saturated NaHCO3 solution to pH=7-8, and then extracted with CH2Cl2 (50 mL×3). The combined organic layer was washed with brine, 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 desired product, (S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one (5005, compound 200 in Table 4) (150 mg, 83% yield) as a white solid.

Workup

  1. extractionextracted with CH2Cl2 (50 mL×3)
  2. washThe combined organic layer was washed with brine
  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-a535b598dc264b018316eafce47dc772
Source dataset
uspto-grants-2013_10
Patent number
US08569323B2

Reaction notes

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