Acetic Acid → HCID 68553228, compound

HRID 2359882Notes

Reaction equation

HRID 2359882 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][CH2:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[O:15][CH3:16].Br[C:22]#[N:23].Cl.[C:25]([OH:28])(=[O:27])[CH3:26]>C(O)C.O1CCOCC1.CCCCC>[C:25]([OH:28])(=[O:27])[CH3:26].[CH3:16][O:15][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=1[CH2:6][N:5]1[CH2:4][C:3]2[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:1]=[C:22]1[NH2:23]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10476Cyanogen BromideHCID 68549502HCID 68549502, compound

Product 1

HCID 68553228HCID 68553228, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8003PentaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.78 g (10.21 mmol) (2-aminobenzyl)(2,6-dimethoxybenzyl)amine and 1.5 g BrCN in 60 mL ethanol was heated at reflux for 10 hours. After evaporation, the resulting residue was dissolved in a small amount of dioxane, mixed with one equivalent 4N HCl in dioxane, the resulting solids were filtered out and dried. The resulting crude product was purified by MPLC (silica gel: Bischoff Prontoprep 60-2540-C18E, 32 μm; mobile phase: CH3CN/H2O+0.1% acetic acid), the resulting product was then dissolved in acetone and converted to the corresponding acetate by adding one equivalent of glacial acetic acid. Stirring the resulting solids [in] n-pentane and drying yielded 580 mg white solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hours
  3. customAfter evaporation
  4. dissolutionthe resulting residue was dissolved in a small amount of dioxane
  5. filtrationthe resulting solids were filtered out
  6. customdried
  7. customThe resulting crude product was purified by MPLC (silica gel: Bischoff Prontoprep 60-2540-C18E, 32 μm; mobile phase: CH3CN/H2O+0.1% acetic acid)
  8. dissolutionthe resulting product was then dissolved in acetone
  9. customdrying

Sources & evidence

ORD record
ord-3e0f1a670855455b8bf6401af7fe231f
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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