Dimethyl Sulfoxide → 1-ethyl-8-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586180노트

반응식

HRID 1586180 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][C:10]=3[Br:17])[CH3:2].CS(C)=O.[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:29][CH2:28][CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][C:10]=3[Br:17])[CH3:2]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 76688CyclohexanemethylamineHCID 212176931-ethyl-4-chloro-8-bromo-1H-pyrazolo[3,4-b]quinoline

생성물 1

HCID 212176961-ethyl-8-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine수율 80.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1-ethyl-4-chloro-8-bromo-1H-pyrazolo[3,4-b]quinoline (2.0 g, 6.44 mmol), DMSO (5 ml) and cyclohexylmethylamine (1.46 g, 12.9 mmol) is heated at 80°-90° C. for 3 hours. The reaction mixture is cooled to room temperature and then is poured into water. The resulting solid is collected by filtration, washed with water and evaporated. The residue is purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1) to afford 2.0 g (80%) of 1-ethyl-8-bromo-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 160°-162° C.

후처리

  1. temperatureis heated at 80°-90° C. for 3 hours
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1)

출처 및 근거

ORD 기록
ord-d76d3cf2bcb344f881c1c13fb32af7e6
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05942520

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