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

HRID 613281노트

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HRID 613281 반응식
[CH3:1][N:2]1[C:6]2=[N:7][C:8]3[C:13]([C:14](Cl)=[C:5]2[C:4]([CH3:16])=[N:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CS(C)=O>O>[CH3:1][N:2]1[C:6]2=[N:7][C:8]3[C:13]([C:14]([NH:24][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:5]2[C:4]([CH3:16])=[N:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 7504BenzylamineHCID 134489994-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinoline

생성물 1

HCID 195922281,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

시약·촉매·용매 1

HCID 962Water용매

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온도
85 °C

실험 절차

A mixture of 1,3-dimethyl-4-chloro-1H-pyrazolo[3,4-b] quinoline (1.2 g, 0.005 mol), benzylamine (1.2 ml) and DMSO (3 ml) was heated at 80-90° C. for 3-4 hours. The reaction mixture was cooled to room temperature and then was poured into water. The mixture was extracted with CH2Cl2 (3×50 ml) and then the CH2Cl2 layers were combined and evaporated. The residue was purified by column chromatography on silca gel eluting with ethyl acetate to afford the product which was crystallized from ether/hexane to afford 1.2 g of 1,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 105° C.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with CH2Cl2 (3×50 ml)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silca gel
  5. washeluting with ethyl acetate
  6. customto afford the product which
  7. customwas crystallized from ether/hexane

출처 및 근거

ORD 기록
ord-2502e3c8515b436b8e5c421ff22c759c
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008226

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