Triethylamine → N'-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamide

HRID 1815002Notes

Reaction equation

HRID 1815002 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=[C:17]([NH2:24])[C:16]=2[N:15]=[C:14]1[CH2:25][CH2:26][CH2:27][CH3:28].[CH3:29][N:30]([CH3:35])[S:31](Cl)(=[O:33])=[O:32]>ClCCl>[NH2:24][C:17]1[C:16]2[N:15]=[C:14]([CH2:25][CH2:26][CH2:27][CH3:28])[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][S:31]([N:30]([CH3:35])[CH3:29])(=[O:33])=[O:32])[C:21]=2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 120210831-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Product 1

HCID 10237612N'-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamideYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.031 mL, 0.23 mmol) was added to a solution of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (67 mg, 0.23 mmol) in dichloromethane (45 mL). The reaction mixture was cooled in an ice bath. Dimethylsulfamoyl chloride (0.025 mL, 0.23 mmol) was added. The reaction mixture was removed from the ice bath. The reaction mixture was allowed to stir at ambient temperature for ˜113 hours. Analysis by HPLC indicated that the reaction was not complete. The dichloromethane was removed under reduced pressure. 1,2-Dichloroethane (50 mL) was added and the reaction mixture was heated to 60° C. After 3 hours, more dimethylsulfamoyl chloride (2.5 μL) was added and heating was continued. After 22 hours the reaction temperature was raised to reflux and the reaction mixture was refluxed for 100 hours. The reaction mixture was extracted twice with water. The aqueous fractions were combined and concentrated under reduced pressure. The resulting residue was recrystallized from methyl acetate to provide 10 mg of N′-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamide as an off-white crystalline solid, m.p. 129.5-131° C. M/Z=397.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customThe reaction mixture was removed from the ice bath
  3. customThe dichloromethane was removed under reduced pressure
  4. addition1,2-Dichloroethane (50 mL) was added
  5. temperaturethe reaction mixture was heated to 60° C
  6. waitAfter 3 hours
  7. additionmore dimethylsulfamoyl chloride (2.5 μL) was added
  8. temperatureheating
  9. temperatureAfter 22 hours the reaction temperature was raised
  10. temperatureto reflux
  11. temperaturethe reaction mixture was refluxed for 100 hours
  12. extractionThe reaction mixture was extracted twice with water
  13. concentrationconcentrated under reduced pressure
  14. customThe resulting residue was recrystallized from methyl acetate

Sources & evidence

ORD record
ord-d194bf1ac42743ce9c8864d3e358ccc2
Source dataset
uspto-grants-2005_04
Patent number
US06878719B2

Reaction notes

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