HCID 178418361, compound → HCID 178482104, compound

HRID 620834Notes

Reaction equation

HRID 620834 reaction equation
Cl[C:2]1[C:3]([NH:22][CH3:23])=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]2[NH:9][C:10]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[C:11]([CH3:13])[N:12]=2)[CH:7]=1.[H][H]>[Pd].C(N(CC)CC)C.CO>[CH3:13][C:11]1[N:12]=[C:8]([C:6]2[CH:7]=[CH:2][C:3]([NH:22][CH3:23])=[CH:4][C:5]=2[O:20][CH3:21])[NH:9][C:10]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178482269HCID 178482269, compound

Product 1

HCID 178482104HCID 178482104, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(5-Chloro-4-methylamino-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.50 g) and 10% palladium on carbon (7.5 g) in a mixture of triethylamine (0.64 ml) and methanol (20 ml) was hydrogenated at ambient temperature under atmospheric pressure of hydrogen gas. After removal of the insoluble substance by filtration, the filtrate was evaporated under reduced pressure. The residue was triturated in diisopropyl ether to give 4-methyl-2-(4-methylamino-2-methoxyphenyl)-5-(3-pyridyl)imidazole (0.10 g).

Workup

  1. customAfter removal of the insoluble substance
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-c9e466bba7d543b7842d537e9757eee3
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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