N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamine → HCID 86686934, compound

HRID 520757Notes

Reaction equation

HRID 520757 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.[F:13][C:14]([F:24])([F:23])[C:15](=[O:22])[CH:16]=[C:17](SC)SC>C(#N)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:10][CH2:11][NH:12][C:17]2=[CH:16][C:15](=[O:22])[C:14]([F:24])([F:23])[F:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10997737N-((6-chloro-3-pyridinyl)methyl)-1,2-ethane-diamineHCID 14127909HCID 14127909, compound

Product 1

HCID 86686934HCID 86686934, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 77 mg (0.42 mmol) of the N-((6-chloropyridin-3-yl)methyl)ethane-1,2-diamine obtained by the foregoing method in 8 mL of anhydrous acetonitrile was added to 60 mg (0.28 mmol) of 1,1,1-trifluoro-4,4-bis(methylthio)-3-buten-2-one obtained by the foregoing method, and the mixture was refluxed under heating for 40 minutes. Following reaction completion, the reaction mixture was returned to room temperature and concentrated under reduced pressure, after which ethyl acetate and water were added, and liquid-liquid extraction was carried out. The organic phase was washed with anhydrous magnesium sulfate, then concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=3:1), giving 59 mg of the target compound (yield, 69%).

Workup

  1. customobtained by the foregoing method
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 40 minutes
  4. customreaction completion
  5. customwas returned to room temperature
  6. concentrationconcentrated under reduced pressure
  7. additionafter which ethyl acetate and water were added
  8. extractionliquid-liquid extraction
  9. washThe organic phase was washed with anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customthe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a0a43ac9fc6e49e8ac44fd5e3359514b
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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