Dimethylamine → HCID 86644290, compound

HRID 1359959Notes

Reaction equation

HRID 1359959 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([N:13](CC)[CH2:14]C)C.S(Cl)(C)(=O)=O.CNC>ClC(Cl)C.CO.O>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([N:13]([CH3:14])[CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15668203HCID 15668203, compound

Product 1

HCID 86644290HCID 86644290, compoundYield 33.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
4 °C

Procedure

1-(6-Bromopyridin-3-yl)ethanol (100 mg, 0.54 mmol) was dissolved in dichloroethane (4 ml), 200 mg of triethylamine was added thereto, and the mixture was stirred at 4° C. under ice cooling. Mesyl chloride (68 mg, 0.60 mmol) was added to the reaction solution. After the dropwise addition, the mixture was stirred at 4° C. under ice cooling and was further stirred at room temperature for 30 min. The reaction solution was poured into 10 ml of iced water and was extracted with 20 ml of ethyl acetate. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under the reduced pressure. The residue was dissolved in DMF (2 ml), and the solution was stirred at room temperature. A 2 M solution (1 ml) of dimethylamine (2 mmol) in methanol was added thereto, and the mixture was stirred at 50° C. for 4 hr. The reaction solution was poured into 10 ml of iced water and was extracted with 20 ml of ethyl acetate. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to give 15 mg (yield 33.1%) of the title compound.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture was stirred at 4° C. under ice cooling
  3. stirringwas further stirred at room temperature for 30 min
  4. extractionwas extracted with 20 ml of ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under the reduced pressure
  8. dissolutionThe residue was dissolved in DMF (2 ml)
  9. stirringthe solution was stirred at room temperature
  10. stirringthe mixture was stirred at 50° C. for 4 hr
  11. extractionwas extracted with 20 ml of ethyl acetate
  12. dry with materialThe extract was dried over anhydrous sodium sulfate
  13. filtrationAfter filtration
  14. concentrationthe filtrate was concentrated under the reduced pressure
  15. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-3326eef0db41445688292e0f7f68103a
Source dataset
uspto-grants-2011_02
Patent number
US07879808B2

Reaction notes

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