2-(2-Aminoethylamino)-5-nitropyridine → [6-(2,4-Dichlorophenyl)-5-imidazolyl(2-pyridyl)]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine

HRID 31855

반응식

HRID 31855 반응식
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1.FC(S(O[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29](S(C(F)(F)F)(=O)=O)[CH:30]=[CH:31][N:32]=2)=[C:24]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=2[Cl:47])[N:23]=1)(=O)=O)(F)F>CN(C)C(=O)C>[Cl:47][C:41]1[CH:42]=[C:43]([Cl:46])[CH:44]=[CH:45][C:40]=1[C:24]1[N:23]=[C:22]([NH:1][CH2:2][CH2:3][NH:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=2)[CH:27]=[CH:26][C:25]=1[C:28]1[NH:32][CH:31]=[CH:30][N:29]=1

참가 물질

4

반응물 2

HCID 1224252-(2-Aminoethylamino)-5-nitropyridineHCID 538229476-(2,4-Dichlorophenyl)-5-{1-[(trifluoromethyl)sulfonyl]imidazol-2-yl}-2-pyridyl (trifluoromethyl)sulfonate

생성물 1

HCID 10238712[6-(2,4-Dichlorophenyl)-5-imidazolyl(2-pyridyl)]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine수율 85%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
40 °C

실험 절차

A suspension of (2-aminoethyl)(5-nitro(2-pyridyl))amine (255 mg, 1.40 mmol) in N,N-dimethylacetamide (3 ml) containing dry powdered 4 Å molecular sieves (50 mg) was added to a suspension of 6-(2,4-dichlorophenyl)-5-{1-[(trifluoromethyl)sulfonyl]imidazol-2-yl}-2-pyridyl (trifluoromethyl)sulfonate (200 mg, 0.35 mmol) in N,N-dimethylacetamide (3 ml) containing dry powdered 4 Å molecular sieves (50 mg). After stirring at 40° C. for 24 h, ethylenediamine (0.5 ml) and water (0.5 ml) were added to the reaction to hydrolyze the one remaining triflate from the product. The reaction was stirred at 85° C. for 2 h and left at room temperature for 12 h. The reaction was then diluted with ethyl acetate (100 ml), filtered, extracted with sat. aq. NaHCO3 (6×30 ml), brine (30 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The product [6-(2,4-dichlorophenyl)-5-imidazol-2-yl(2-pyridyl)]{2-[(5-nitro(2-pyridyl))amino]ethyl}amine (79859) was obtained as a yellow glass weighing 143 mg in 85% yield.

후처리

  1. additioncontaining
  2. customdry powdered 4 Å molecular sieves (50 mg)
  3. additioncontaining
  4. customdry powdered 4 Å molecular sieves (50 mg)
  5. additionethylenediamine (0.5 ml) and water (0.5 ml) were added to the reaction
  6. stirringThe reaction was stirred at 85° C. for 2 h
  7. waitleft at room temperature for 12 h
  8. additionThe reaction was then diluted with ethyl acetate (100 ml)
  9. filtrationfiltered
  10. extractionextracted with sat. aq. NaHCO3 (6×30 ml), brine (30 ml)
  11. dry with materialdried with Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-71762ba3269f47cda8b6110539750a2f
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425557B2

연결된 노트

불러오는 중…