Acetic Anhydride → HCID 59728108, compound

HRID 2043338Notes

Reaction equation

HRID 2043338 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:28](OC(=O)C)(=[O:30])[CH3:29]>C(O)C.[Pd].O1CCCC1>[N:9]1[CH:10]=[C:6]([CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[C:19]2[CH:20]=[C:21]([NH:25][C:28](=[O:30])[CH3:29])[CH:22]=[CH:23][CH:24]=2)[NH:7][CH:8]=1

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 66751577HCID 66751577, compound

Product 1

HCID 59728108HCID 59728108, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Isopropyl-(3-nitro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-ylmethyl]-amine (0.055 g, 0.14 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 toluene (1.5 ml) and tetrahydrofuran (3 ml), acetic anhydride (0.015 mg, 0.14 mmol) was added and the mixture was stirred overnight. The solvents were evaporated and the residue was partitioned between sodium bicarbonate solution and ethyl acetate. The organic layer was dried over magnesium sulphate and evaporated. The residue was dissolved in tetrahydrofuran (5 ml) and tetrabutylammonium fluoride solution (0.3 ml, 1M) in tetrahydrofuran was added. After stirring the mixture at 65° C. overnight the solvent was evaporated and the residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=95:5) to yield a white gum, (0.005 g, 34%); MS (ISP): 273.2 ((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 toluene (1.5 ml)
  7. customThe solvents were evaporated
  8. customthe residue was partitioned between sodium bicarbonate solution and ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulphate
  10. customevaporated
  11. dissolutionThe residue was dissolved in tetrahydrofuran (5 ml)
  12. additiontetrabutylammonium fluoride solution (0.3 ml, 1M) in tetrahydrofuran was added
  13. stirringAfter stirring the mixture at 65° C. overnight the solvent
  14. customwas evaporated
  15. customthe residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=95:5)
  16. customto yield a white gum, (0.005 g, 34%)

Sources & evidence

ORD record
ord-12162eb6e7b846179350247835e81b96
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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