Ammonium formate → HCID 18470873, compound

HRID 2228780Notes

Reaction equation

HRID 2228780 reaction equation
C([O-])=O.[NH4+].[C:5]([O:9][C:10]([N:12]([CH3:46])[CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:18]=[C:19]([CH:43]=[CH:44][CH:45]=1)[CH2:20][CH2:21][NH:22][C:23]1[C:24](=[O:42])[N:25]([CH2:31][C:32]([O:34]CC2C=CC=CC=2)=[O:33])[C:26]([CH3:30])=[C:27](Cl)[N:28]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>[Pd].CO>[C:5]([O:9][C:10]([N:12]([CH3:46])[CH2:13][CH2:14][O:15][CH2:16][C:17]1[CH:18]=[C:19]([CH:43]=[CH:44][CH:45]=1)[CH2:20][CH2:21][NH:22][C:23]1[C:24](=[O:42])[N:25]([CH2:31][C:32]([OH:34])=[O:33])[C:26]([CH3:30])=[CH:27][N:28]=1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18470952HCID 18470952, compound

Product 1

HCID 18470873HCID 18470873, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (368 mg, 5.83 mmol), followed by 10% palladium on charcoal (200 mg), were added to a solution of benzyl 2-[3-{[3-({2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy}methyl)phenethyl]amino}-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 113) (350 mg, 0.58 mmol) in methanol (10 ml), and the reaction stirred at room temperature ovemight. The reaction mixture was filtered through Whatman® fibre, and the filtrate concentrated under reduced pressure. The residue was triturated with dichloromethane, the resulting suspension filtered again through Whatman® fibre, then through celite, and this filtrate evaporated under reduced pressure. The residual solid was dissolved in dichloromethane, the solution washed with water, brine, then dried over MgSO4 and evaporated under reduced pressure to give the desired product as a gum, (213 mg, 79%).

Workup

  1. filtrationThe reaction mixture was filtered through Whatman® fibre
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was triturated with dichloromethane
  4. filtrationthe resulting suspension filtered again through Whatman® fibre
  5. customthrough celite, and this filtrate evaporated under reduced pressure
  6. dissolutionThe residual solid was dissolved in dichloromethane
  7. washthe solution washed with water, brine
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-413fde423c914f33a652287f329a3724
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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