HCID 117678023, compound → HCID 57406855, compound

HRID 623668Notes

Reaction equation

HRID 623668 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[N:7]=[N:8][N:9]([C:24]2[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[C:27]([O:33]CC3C=CC=CC=3)=[CH:26][C:25]=2[O:41]CC2C=CC=CC=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[CH2:1]([NH:3][C:4]([C:6]1[N:7]=[N:8][N:9]([C:24]2[CH:29]=[C:28]([CH:30]([CH3:31])[CH3:32])[C:27]([OH:33])=[CH:26][C:25]=2[OH:41])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 117678023HCID 117678023, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57406855HCID 57406855, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Pd(OH)2/C (0.01 mmol) was added to the intermediate obtained in Step F (0.1 mmol) dissolved in EtOH (5 ml) and the resulting mixture was subjected to hydrogenation under one atmosphere of hydrogen for 1 hour. The catalyst was filtered off through a Celite® pad and the ethanol was removed under reduced pressure. The reaction mixture was purified by column chromatography (DCM/MeOH:90/10) to obtain the title compound as an oil.

Workup

  1. filtrationThe catalyst was filtered off through a Celite® pad
  2. customthe ethanol was removed under reduced pressure
  3. customThe reaction mixture was purified by column chromatography (DCM/MeOH:90/10)

Sources & evidence

ORD record
ord-cee30b68183b48b7b34fedce5a043550
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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