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

HRID 375896ノート

反応式

HRID 375896 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) was heated at 80°-90° C. for 3 hours. The reaction mixture was cooled to room temperature and then was poured into water. The resulting solid was collected by filtration, washed with water and evaporated. The residue was 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. temperaturewas heated at 80°-90° C. for 3 hours
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel eluting with CH2Cl2 /ether (9/1)

出典と根拠

ORDレコード
ord-5808fd0d6173443ba64c4844ad58e6dc
出典データセット
uspto-grants-1996_01
特許番号
US05488055

反応ノート

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