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

HRID 1586180ノート

反応式

HRID 1586180 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d76d3cf2bcb344f881c1c13fb32af7e6
出典データセット
uspto-grants-1999_08
特許番号
US05942520

反応ノート

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