Ammonium formate → HCID 86756338, compound

HRID 2228770Notes

Reaction equation

HRID 2228770 reaction equation
C([O-])=O.[NH4+].[CH3:5][C@@H:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[C@@H:8]([CH2:18][NH:19][C:20]2[C:21](=[O:39])[N:22]([CH2:28][C:29]([O:31]CC3C=CC=CC=3)=[O:30])[C:23]([CH3:27])=[C:24](Cl)[N:25]=2)[CH2:7]1>[Pd].CO>[CH3:5][C@@H:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:17])[C:13]([F:14])([F:16])[F:15])[C@@H:8]([CH2:18][NH:19][C:20]2[C:21](=[O:39])[N:22]([CH2:28][C:29]([OH:31])=[O:30])[C:23]([CH3:27])=[CH:24][N:25]=2)[CH2:7]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86756339HCID 86756339, compound

Product 1

HCID 86756338HCID 86756338, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

10% Palladium on charcoal (200 mg), followed by ammonium formate (1.1 g, 17.4 mmol) were added to a solution of benzyl 2-[3-({[(2R,4R)-4-methyl-1-(2,2,2-trifluoroacetyl)piperidinyl]methyl}amino)-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 90) (900 mg, 1.74 mmol) in methanol (20 ml) and the reaction was stirred at room temperature ovemight. Additional 10% palladium on charcoal (50 mg) was added and the reaction stirred for a further 24 hrs. The mixture was filtered through Whatman® fibre and the filtrate concentrated under reduced pressure. The residue was suspended in a methanol:dichloromethane (10:90) solution, the resulting precipitate filtered off, and the filtrate evaporated under reduced pressure to provide the title compound as a white solid, (600 mg, 92%). LRMS: m/z=391 (M+1)+.

Workup

  1. stirringthe reaction stirred for a further 24 hrs
  2. filtrationThe mixture was filtered through Whatman® fibre
  3. concentrationthe filtrate concentrated under reduced pressure
  4. filtrationthe resulting precipitate filtered off
  5. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-60a57f17a3d24b6ab02db87fe521a7b3
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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