HCID 66751577, compound → HCID 59728037, compound

HRID 2043337Notes

Reaction equation

HRID 2043337 reaction equation
[CH:1]([N:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1)[CH2:5][C:6]1[N:7](COCC[Si](C)(C)C)[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[N:9]1[CH:10]=[C:6]([CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)[NH:7][CH:8]=1

Participants

4

Reactant 1

HCID 66751577HCID 66751577, compound

Product 1

HCID 59728037HCID 59728037, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Isopropyl-(3-nitro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-ylmethyl]-amine (0.2 g, 0.51 mmol) was dissolved in ethanol, palladium on charcoal (20 mg, 10% Pd) was added and the mixture was hydrogenated overnight. The catalyst was filtered off and the solvent was evaporated. The residue was dissolved in ethyl acetate and filtered over silica gel. After evaporation the residue was dissolved in hydrochloric acid in ethanol (5M, 1 ml) and stirred at 60° C. for 2 hours. The solvent was evaporated and the residue was partitioned between sodium hydroxide solution (10%) and dichloromethane. After separation the aqueous layer was extracted again with dichloromethane. The combined organic layers were dried over magnesium sulphate and evaporated. The residue was purified using flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=90:10) to yield a light yellow gum, (0.054 g, 51%); MS (ISP): 231.4 ((M+H)+.).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered over silica gel
  5. customAfter evaporation the residue
  6. dissolutionwas dissolved in hydrochloric acid in ethanol (5M, 1 ml)
  7. customThe solvent was evaporated
  8. customthe residue was partitioned between sodium hydroxide solution (10%) and dichloromethane
  9. customAfter separation the aqueous layer
  10. extractionwas extracted again with dichloromethane
  11. dry with materialThe combined organic layers were dried over magnesium sulphate
  12. customevaporated
  13. customThe residue was purified
  14. customto yield a light yellow gum, (0.054 g, 51%)

Sources & evidence

ORD record
ord-77503d137cf94b3ca0d1cbefffc6ee00
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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