1-Chloro-2-(diethylamine)ethane hydrochloride → 1-(4-chlorophenyl)-3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carboxamide trifluoroacetate

HRID 495646노트

반응식

HRID 495646 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=3[NH:10][C:9]2=[O:23])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26][CH2:27][N:28]([CH2:31][CH2:32]Cl)[CH2:29][CH3:30].Cl.[C:35](=[O:38])(O)[O-:36].[Na+]>CN(C)C=O.C(N(CC)CC)C>[F:20][C:19]([F:22])([F:21])[C:35]([OH:36])=[O:38].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([C:19]([F:21])([F:20])[F:22])=[CH:14][C:15]([C:17]([NH2:18])=[O:36])=[CH:16][C:11]=3[N:10]([CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:9]2=[O:23])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 223273651-(4-chlorophenyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile

생성물 1

HCID 98080931-(4-chlorophenyl)-3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carboxamide trifluoroacetate수율 30%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

1-(4-Chlorophenyl)-2-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-benzimidazole-5-carbonitrile (0.1767 g) was dissolved in N,N-dimethylformamide (5 ml), and to the solution was added sodium hydride (27.2 mg). The mixture was stirred at room temperature for 5 minutes. To the mixture were added 2-chlorotriethylamine hydrochloride (117.1 mg) and triethylamine (0.109 ml), and the mixture was stirred at 60-70° C. for 1 hour. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant residue was dissolved in 2-methyl-2-propanol (15 ml) and heated at 50° C. To the solution was added powdered potassium hydroxide (0.7340 g), and the mixture was stirred for 1 hour. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant residue was purified by HPLC using condition 1 to give the title compound (90.4 mg, 30%).

후처리

  1. stirringthe mixture was stirred at 60-70° C. for 1 hour
  2. temperatureto cool, to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resultant residue was dissolved in 2-methyl-2-propanol (15 ml)
  8. temperatureheated at 50° C
  9. additionTo the solution was added powdered potassium hydroxide (0.7340 g)
  10. stirringthe mixture was stirred for 1 hour
  11. temperatureto cool, to the reaction mixture
  12. additionwas added saturated aqueous sodium bicarbonate solution
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe organic layer was washed with saturated brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. concentrationconcentrated in vacuo
  17. customThe resultant residue was purified by HPLC

출처 및 근거

ORD 기록
ord-23b03dd0d7a4489fa197cf057623e477
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939887B2

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