Ammonium formate → 2-[3-{[3-({2-[(tert-Butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

HRID 2228777Notes

Reaction equation

HRID 2228777 reaction equation
C([O-])=O.[NH4+].[C:5]([O:9][C:10]([NH:12][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].C(#N)C>[C:5]([O:9][C:10]([NH:12][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])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18470846benzyl 2-[3-{[3-({2-[(tert-butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate

Product 1

HCID 184709262-[3-{[3-({2-[(tert-Butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acidYield 58.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

Ammonium formate (425 mg, 6.74 mmol) and 10% palladium on charcoal (200 mg) was added to a solution of benzyl 2-[3-{[3-({2-[(tert-butoxycarbonyl)amino]ethoxy}methyl)phenethyl]amino}-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 106) (392 mg, 0.67 mmol) in acetonitrile (10 ml), and the reaction stirred at room temperature overnight. The reaction mixture was filtered through Whatman® fibre, and the filtrate concentrated under reduced pressure. The residue was suspended in dichloromethane, basified using 1N NaOH solution, and re-acidified to pH 4, using 1N hydrochloric acid. This solution was extracted with ethyl acetate (3×), and the combined organic extracts dried over MgSO4 and evaporated under reduced pressure to give the title compound as a white foam, (180 mg, 58%).

Workup

  1. filtrationThe reaction mixture was filtered through Whatman® fibre
  2. concentrationthe filtrate concentrated under reduced pressure
  3. extractionThis solution was extracted with ethyl acetate (3×)
  4. dry with materialthe combined organic extracts dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-33214c5bd05a48d2ab9c8608f382ef4e
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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