1H-1,2,4-Triazole → HCID 61709244, compound

HRID 340468Notes

Reaction equation

HRID 340468 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC.Cl[C:23]1[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][N:24]=1>[Cu](I)I.O.CN(C=O)C>[N:1]1([C:23]2[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][N:24]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 844322-Chloropyridin-4-amineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 61709244HCID 61709244, compoundYield 4.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1H-1,2,4-triazole (540 mg), cesium carbonate (1.9 g), trans-N,N′-dimethylcyclohexane-1,2-diamine (74 mg), and copper iodide (50 mg) were added to a tube containing a DMF (5 ml) solution containing 2-chloropyridin-4-amine (500 mg) and the tube was sealed, followed by stirring at 150° C. for 14.5 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 10:1), and a brown solid of 2-(1H-1,2,4-triazol-1-yl)pyridin-4-amine (25.8 mg) was thus obtained.

Workup

  1. customthe tube was sealed
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 10:1)

Sources & evidence

ORD record
ord-79400f65fe86406dbee998f52316e8fa
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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