Sodium Bicarbonate → HCID 178423750, compound

HRID 1627220Notes

Reaction equation

HRID 1627220 reaction equation
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2C2CCCCO2)=[C:4]([NH:17][CH:18]([C:20]2[N:21]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22](=[O:31])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:30])[CH3:19])[N:3]=1.C([O-])(O)=O.[Na+].[F:43][C:44]1[N:52]=[C:51]2[C:47]([N:48]=[CH:49][NH:50]2)=[C:46]([NH:53][CH:54]([C:56]2[N:57]([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[C:58](=[O:67])[C:59]3[C:64]([CH:65]=2)=[CH:63][CH:62]=[CH:61][C:60]=3[CH3:66])[CH3:55])[N:45]=1>Cl.CCO>[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:17][C@H:18]([C:20]2[N:21]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:22](=[O:31])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:30])[CH3:19])[N:3]=1.[F:43][C:44]1[N:52]=[C:51]2[C:47]([N:48]=[CH:49][NH:50]2)=[C:46]([NH:53][CH:54]([C:56]2[N:57]([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[C:58](=[O:67])[C:59]3[C:64]([CH:65]=2)=[CH:63][CH:62]=[CH:61][C:60]=3[CH3:66])[CH3:55])[N:45]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 69033406HCID 69033406, compound2×HCID 178423750HCID 178423750, compound

Product 2

HCID 178423750HCID 178423750, compoundYield 94%HCID 178423764HCID 178423764, compound

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

3-(1-(2-Fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 5203) (160 mg, 0.32 mmol) was dissolved in HCl/EtOH (3 M, 5 mL) and the resulting mixture was stirred at room temperature for 1 h. The mixture was neutralized with saturated NaHCO3 aqueous solution to pH=7-8, and 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. The solid was collected by filtration and dried in vacuo to afford the desired product, 3-(1-(2-fluoro-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 5204) (125 mg, 94% 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
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6a0c32c266ca49f29fe9a0ff453628bf
Source dataset
uspto-grants-2014_07
Patent number
US08785456B2

Reaction notes

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