HCID 367509, compound → HCID 136133153, compound

HRID 1046828Notes

Reaction equation

HRID 1046828 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].[CH3:19][C:20]1[NH:21][C:22]([NH2:25])=[N:23][N:24]=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:23]3[N:24]=[C:20]([CH3:19])[N:21]=[C:22]3[NH:25][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 178434112HCID 178434112, compound

Product 1

HCID 136133153HCID 136133153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Under an atmosphere of argon, ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (381 mg, 1.6 mmol) and 5-methyl-4H-1,2,4-triazole-3-amine (200 mg, 2.0 mmol, 1.3 eq.) were dissolved in DMF (4 ml), and solid sodium bicarbonate (659 mg, 7.8 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 (300 mg, 46% 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 (300 mg, 46% of theory)

Sources & evidence

ORD record
ord-ddd8198a9ac644fa95030df94616c8fe
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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