Triethylamine → HCID 58289842, compound

HRID 2088743Notes

Reaction equation

HRID 2088743 reaction equation
CS(Cl)(=O)=O.[CH2:6]([N:8]([CH2:11]C)[CH2:9][CH3:10])C.[N+:13]([C:16]1[CH:25]=C2[C:19]([CH2:20][CH2:21][CH2:22]C2O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>O1CCCC1>[CH3:11][N:8]([CH3:6])[CH:9]1[C:10]2[C:19](=[CH:18][CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:25]=2)[CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110087787-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 58289842HCID 58289842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

With cooling with ice, 0.16 mL of methanesulfonyl chloride and 0.29 mL of triethylamine were added to a tetrahydrofuran (5 mL) solution of 200 mg of 7-nitro-1,2,3,4-tetrahydronaphthalen-1-ol obtained according to the method described in WO2004/087124, and stirred for 1 hour. The insoluble matter was removed through filtration through Celite, the solvent was evaporated away from the filtrate, the residue was dissolved in 3 mL of N,N-dimethylformamide, then 1.55 mL of 2 M dimethylamine/tetrahydrofuran solution was added to it, and stirred overnight at 60° C. After left cooled, water was added to the reaction solution, and then diluted with ethyl acetate. The organic layer was washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 100 mg of the entitled compound as a yellow oil.

Workup

  1. customobtained
  2. customThe insoluble matter was removed through filtration through Celite
  3. customthe solvent was evaporated away from the filtrate
  4. dissolutionthe residue was dissolved in 3 mL of N,N-dimethylformamide
  5. addition1.55 mL of 2 M dimethylamine/tetrahydrofuran solution was added to it
  6. stirringstirred overnight at 60° C
  7. waitAfter left
  8. temperaturecooled
  9. additionwater was added to the reaction solution
  10. additiondiluted with ethyl acetate
  11. washThe organic layer was washed with water and saturated saline water
  12. dry with materialdried with anhydrous sodium sulfate
  13. customThe solvent was evaporated away
  14. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-89c2d9e4559e4b728eb84b7d10b4d331
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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