Methanol → HCID 66713064, compound

HRID 1618267Notes

Reaction equation

HRID 1618267 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10](Cl)[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7].C([O-])(=O)C.[Na+].CO>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7]

Participants

6

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 86014604HCID 86014604, compound

Product 1

HCID 66713064HCID 66713064, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [(1-chloro-4-phenyl-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester (177 mg, 0.5 mmol, Example D-74 b), Pd/C (50 mg, 10 wt % Pd), sodium acetate (49 mg, 0.6 mmol), MeOH (10 ml) and EtOAc (5 ml) was stirred under a H2-atmosphere at ambient pressure and temperature for 2 h. Then the mixture was filtered through a pad of celite. Celite and filter cake were washed thoroughly with EtOAc and the combined organic phases were concentrated in vacuo. To the residue was added concentrated aqueous NaHCO3 (10 ml) and the mixture was extracted with EtOAc (2×15 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a colorless gum (154 mg); MS-(+)-ion: M+1=321.0.

Workup

  1. filtrationThen the mixture was filtered through a pad of celite
  2. filtrationCelite and filter cake
  3. washwere washed thoroughly with EtOAc
  4. concentrationthe combined organic phases were concentrated in vacuo
  5. additionTo the residue was added concentrated aqueous NaHCO3 (10 ml)
  6. extractionthe mixture was extracted with EtOAc (2×15 ml)
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd9f8c14694942e2a61ebd94e985600a
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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