Benzoyl chloride → N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamide

HRID 1060662

반응식

HRID 1060662 반응식
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].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(S(O)(=O)=O)C>ClCCl.C(O)(C)C>[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][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:21]=2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=1

참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11668Ethanesulfonic acidHCID 120210831-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

생성물 1

HCID 10216053N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamide수율 56.4%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

실험 절차

Triethylamine (0.07 mL, 0.5 mmol) was added to a solution of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (150 mg, 0.5 mmol) in dichloromethane (150 mL). The reaction mixture was cooled in an ice bath. Benzoyl chloride (0.07 mL, 0.5 mmol) was added and the reaction mixture was removed from the ice bath. The reaction mixture was washed twice with water and then concentrated under reduced pressure. The resulting residue was purified by flash chromatography eluting with 10% methanol in dichloromethane to provide an oily brown material. This material was dissolved in a minimum amount of isopropanol and then ethanesulfonic acid (55 mg, 0.5 mmol) was added with stirring. The reaction mixture was stirred at ambient temperature for ˜1 hour and then heated briefly in a sand bath until it became homogeneous. The solution was allowed to cool to ambient temperature and then was chilled in an ice bath. The resulting precipitate was isolated by filtration to provide 111 mg of N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamide as a crystalline solid, m.p. 127.8-128.8° C. Analysis: Calculated for C23H31N5O: % C, 70.20; % H, 7.94; % N, 17.80; Found: % C, 69.82; % H, 7.70; % N, 17.68.

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customthe reaction mixture was removed from the ice bath
  3. washThe reaction mixture was washed twice with water
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with 10% methanol in dichloromethane
  7. customto provide an oily brown material
  8. stirringThe reaction mixture was stirred at ambient temperature for ˜1 hour
  9. temperatureheated briefly in a sand bath until it
  10. temperaturewas chilled in an ice bath
  11. customThe resulting precipitate was isolated by filtration

출처 및 근거

ORD 기록
ord-c7c9995ba1fe4274a2bf60052de5dfac
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525064B1

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