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

HRID 977138ノート

反応式

HRID 977138 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  1. temperaturewas heated at 80°-90° C. for 3-4 hours
  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

出典と根拠

ORDレコード
ord-aa6724bf8f044a76a43b269a4c04b262
出典データセット
uspto-grants-1997_03
特許番号
US05614530

反応ノート

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