HCID 25537343, compound → HCID 57422461, compound

HRID 1770543Notes

Reaction equation

HRID 1770543 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[N:10]=[CH:9]2)=[C:5]([CH3:16])[O:4][N:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[N:10]=[CH:9]2)=[C:5]([CH3:16])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 25537343HCID 25537343, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57422461HCID 57422461, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,5-dimethyl-4-((4-nitro-1H-imidazol-1-yl)methyl)isoxazole (example 10-40b) (1.0 g, 4.5 mmol) and 10% palladium on charcoal (200 mg) in methanol (40 mL) was shaken on a Parr shaker under a pressure of 2.5 bar hydrogen for 2 hours. Filtration through a plug of celite followed by rotary evaporation afforded 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-imidazol-4-amine as a yellowish-red solid (800 mg, 93% yield). MS M+H calculated 193. Found 193.

Workup

  1. filtrationFiltration through a plug of celite
  2. customfollowed by rotary evaporation

Sources & evidence

ORD record
ord-c9bfdeabf8374b7a82e3804e82f8b0b2
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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