HCID 367509, compound → HCID 3154565, compound

HRID 1046825Notes

Reaction equation

HRID 1046825 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].[NH:19]1[CH:23]=[N:22][C:21]([NH2:24])=[N:20]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH:7]2[N:20]3[N:19]=[CH:23][N:22]=[C:21]3[NH:24][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 367509HCID 367509, compoundHCID 516892Sodium BicarbonateHCID 178418311HCID 178418311, compound

Product 1

HCID 3154565HCID 3154565, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Under an atmosphere of argon, ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (300 mg, 1.2 mmol) and 1H-1,2,4-triazole-3-amine (130 mg, 1.5 mmol, 1.2 eq.) were dissolved in DMF (3 ml) and solid sodium bicarbonate (518 mg, 6.2 mmol, 5 eq.) was added. The mixture was stirred at 65° C. for 12 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (233 mg, 50% of theory).

Workup

  1. filtrationThe mixture was then filtered
  2. distillationthe DMF from the filtrate was distilled off under reduced pressure
  3. customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (233 mg, 50% of theory)

Sources & evidence

ORD record
ord-749e48ba03ae47c8b42eee7f0eb4599b
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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