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Diisopropylethylamine → 5-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amine

HRID 2178327
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HRID 2178327 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][NH2:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1.Cl[C:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][C:25]([I:31])=[CH:24][N:23]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[I:31][C:25]1[CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:22]([NH:20][CH2:19][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]3[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:23][CH:24]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 15142942-Chloro-5-iodo-3-nitropyridineHCID 118113971(3-Methoxy-4((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine

생성물 1

HCID 1181139925-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amine수율 85%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a stirred solution of (3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine (9.11 g, 33.21 mmol) in acetonitrile (150 mL) was added 2-chloro-5-iodo-3-nitropyridine (9.90 g, 34.81 mmol) and N,N-diisopropylethylamine (6.44 g, 49.81 mmol). The yellow solution was heated to reflux and stirred. After 3 h, the red-brown mixture was cooled to 0° C. resulting in the formation of a precipitate. The precipitate was isolated by filtration and washed with acetonitrile (50 mL) and water (200 mL). The moist solids were dissolved in dichloromethane, and a small amount of water separated and was removed. The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 14.67 g (85%) of 5-iodo-N-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3-nitropyridin-2-amine as a yellow-brown solid.

후처리

  1. temperatureThe yellow solution was heated
  2. temperatureto reflux
  3. customresulting in the formation of a precipitate
  4. customThe precipitate was isolated by filtration
  5. washwashed with acetonitrile (50 mL) and water (200 mL)
  6. dissolutionThe moist solids were dissolved in dichloromethane
  7. customa small amount of water separated
  8. customwas removed
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6de989ea929d4786baaed83a70ecfff1
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067914B1

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