Bis(2-amino-1H-imidazole) sulphate → HCID 58032564, compound

HRID 1046833Notes

Reaction equation

HRID 1046833 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH:7]=[C:8]([C:14](=O)[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)#[N:2].S(O)(O)(=O)=O.[NH:24]1[CH:28]=[CH:27][N:26]=[C:25]1[NH2:29].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH:7]2[N:24]3[CH:28]=[CH:27][N:26]=[C:25]3[NH:29][C:14]([CH3:15])=[C:8]2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 367509HCID 367509, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 58032564HCID 58032564, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Under an atmosphere of argon, ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (1.42 g, 5.82 mmol) and 1H-imidazole-2-amine sulfate (2:1) (1000 mg, 3.78 mmol, 0.65 eq.) were dissolved in DMF (10 ml), and solid sodium bicarbonate (1.96 g, 23.3 mmol, 4 eq.) was added. The mixture was stirred at 65° C. for 12 h. The mixture was then filtered through kieselguhr, and the DMF from the filtrate was distilled off under reduced pressure. Acetonitrile (10 ml) was added to the residue. The precipitated product was filtered off, washed with ethanol and dried under high vacuum, which gave a first product fraction (503 mg). The concentrated filtrate was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA) and lyophilized. This gave 778 mg as a further product fraction (total yield: 71% of theory).

Workup

  1. filtrationThe mixture was then filtered through kieselguhr
  2. distillationthe DMF from the filtrate was distilled off under reduced pressure
  3. additionAcetonitrile (10 ml) was added to the residue
  4. filtrationThe precipitated product was filtered off
  5. washwashed with ethanol
  6. customdried under high vacuum, which
  7. customgave a first product fraction (503 mg)
  8. customThe concentrated filtrate was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)

Sources & evidence

ORD record
ord-f04cdab25e834ee9b700c8b878466434
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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