HCID 367509, compound → HCID 136133155, compound

HRID 2200926Notes

Reaction equation

HRID 2200926 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][O:20][C:21]1[NH:25][N:24]=[C:23]([NH2:26])[N:22]=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:24]3[N:25]=[C:21]([O:20][CH3:19])[N:22]=[C:23]3[NH:26][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 178494246HCID 178494246, compound

Product 1

HCID 136133155HCID 136133155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Under an atmosphere of argon, ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (297 mg, 1.2 mmol) and 5-methoxy-1H-1,2,4-triazole-3-amine (153 mg, 1.3 mmol, 1.1 eq.) were dissolved in DMF (2.5 ml), and solid sodium bicarbonate (513 mg, 6.1 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 (191 mg, 42% 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 (191 mg, 42% of theory)

Sources & evidence

ORD record
ord-7aaf5a9267f64bf7ae9bc6de2407c5da
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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