HCID 178435781, compound → HCID 178435782, compound

HRID 709948Notes

Reaction equation

HRID 709948 reaction equation
[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15](=[O:25])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH:23]=[CH2:24])[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1>CO.[Pd]>[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15](=[O:25])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][CH3:24])[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

4

Reactant 1

HCID 178435781HCID 178435781, compound

Product 1

HCID 178435782HCID 178435782, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-2-phenyl-8-vinylisoquinolin-1(2H)-one (8) (120 mg, 0.29 mmol) and palladium (10% weight on carbon, 24 mg) in anhydrous MeOH (25 mL) was degassed and flushed with hydrogen (three cycles). The reaction mixture was stirred under a hydrogen atmosphere (hydrogen balloon) at RT for 1 h. The mixture was filtered through Celite and rinsed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by ISCO (silica gel cartridge, 0-10% MeOH-DCM) to afford the product, (S)-3-(1-((9H-purin-6-yl)amino)ethyl)-8-ethyl-2-phenylisoquinolin-1(2H)-one (9). ESI-MS m/z: 411.2 [M+H]+.

Workup

  1. customwas degassed
  2. customflushed with hydrogen (three cycles)
  3. filtrationThe mixture was filtered through Celite
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by ISCO (silica gel cartridge, 0-10% MeOH-DCM)

Sources & evidence

ORD record
ord-b35e410526aa4a3983499b952badbf33
Source dataset
uspto-grants-2015_11
Patent number
US09181221B2

Reaction notes

Loading…