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Dimethyl Sulfoxide → 1-ethyl-N-(4-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 977132
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HRID 977132 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 773174-PyridinemethanamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

생성물 1

HCID 195922291-ethyl-N-(4-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine수율 34.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and 4-(aminomethyl)pyridine (0.92 ml, 9 mmol) was heated at 80°-90° C. overnight. The reaction mixture was poured into water (200 ml)NH4OH (1 ml) and the mixture was extracted with CH2Cl2 (3×100 ml). The CH2Cl2 layers were combined, dried over MgSO4 and evaporated. The residue was crystallized from ethyl acetate and recrystallized from ethyl acetate to afford 450 mg of 1-ethyl-N-(4-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 191°-192° C.

후처리

  1. temperaturewas heated at 80°-90° C. overnight
  2. extractionthe mixture was extracted with CH2Cl2 (3×100 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was crystallized from ethyl acetate
  6. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-af8fc84deb9d4ddfa17cd07c0fdead3a
출처 데이터셋
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05614530

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