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

HRID 11342

反応式

HRID 11342 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f4478d06628b43f99b4b9e1ba58a7ed6
出典データセット
uspto-grants-2006_08
特許番号
US07098221B2

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