Hydrazine hydrate (1:1) → 1-(4-aminobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1984426

反応式

HRID 1984426 の反応式
[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:30][CH3:31])[C:14]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.O.NN>C(O)C>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1[N:13]([CH2:30][CH3:31])[N:12]=[C:11]2[C:10]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:3]=[C:2]2[NH2:1]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 577175922-[4-(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]isoindole-1,3-dione

生成物 1

HCID 669586561-(4-aminobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine収率 87.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-[4-(4-Amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]isoindole-1,3-dione (prepared as described in Example 22, 7.10 g, 17.2 mmol), hydrazine hydrate (4.20 mL, 85.9 mmol), and ethanol (213 mL) were combined and heated at reflux for 30 minutes. The solution was allowed to cool to ambient temperature, then was cooled to 0° C. A white solid precipitated from the solution and was isolated by filtration and washed with ethanol. The crude product was purified by chromatography on a HORIZON HPFC system (silica, gradient elution with 10%-75% CMA in chloroform). The appropriate fractions were combined and concentrated under reduced pressure to afford 4.25 g of 1-(4-aminobutyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine.

後処理

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. temperaturewas cooled to 0° C
  4. customA white solid precipitated from the solution
  5. customwas isolated by filtration
  6. washwashed with ethanol
  7. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica, gradient elution with 10%-75% CMA in chloroform)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-49eda0a51a0b4c9382f09629f0a90e98
出典データセット
uspto-grants-2009_06
特許番号
US07544697B2

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