HCID 19365524, compound → HCID 19365514, compound

HRID 849938Notes

Reaction equation

HRID 849938 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:16]=2)=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][CH:4]=[C:5]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:19])([F:20])[F:18])=[CH:15][N:16]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 19365524HCID 19365524, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 19365514HCID 19365514, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

First, 79 mg of 10% palladium/carbon was added to a solution of 0.30 g of 3-(4-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-13) in 12 ml of ethyl acetate under an atmosphere of nitrogen, which was then replaced with hydrogen under a pressure of 1 atm., and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered through celite and concentrated. The residue was subjected to silica gel column chromatography, which afforded 0.13 g (yield, 47%) of 3-(5-amino-4-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-19).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-65262d1b7e8a4fd2a12201a778586867
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

Loading…