Sodium Iodide → N-[4-(4-amino-2-methyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]methanesulfonamide

HRID 1984490

反応式

HRID 1984490 の反応式
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].Cl[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]([CH3:27])[N:15]=[C:16]2[C:25]=1[C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:18]=[C:17]2[NH2:26].[I-].[Na+]>CN(C=O)C>[NH2:26][C:17]1[C:16]2=[N:15][N:14]([CH3:27])[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[C:25]2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 577175021-(4-chlorobutyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine

生成物 1

HCID 57717637N-[4-(4-amino-2-methyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]methanesulfonamide収率 38.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

Methanesulfonamide (1.5 g, 16.5 mmol) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 0.660 g, 16.5 mmol) in DMF (10 mL); the reaction was stirred for five minutes. 1-(4-Chlorobutyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine (0.952 g, 3.3 mmol) in DMF (1 mL) and sodium iodide (123 mg, 0.825 mmol) were sequentially added. The reaction was heated at 80° C. for four hours, allowed to cool to ambient temperature, and poured into ice water (70 mL). The resulting mixture was extracted with dichloromethane (6×50 mL), and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified twice by chromatography using a HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform first and 5-10% methanol in dichloromethane second) followed by recrystallizafion from acetonitrile to provide 440 mg of N-[4-(4-amino-2-methyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]methanesulfonamide as light tan crystals, mp 188-189° C.

後処理

  1. temperatureto cool to ambient temperature
  2. extractionThe resulting mixture was extracted with dichloromethane (6×50 mL)
  3. dry with materialthe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified twice by chromatography
  7. washa HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform first and 5-10% methanol in dichloromethane second)

出典と根拠

ORDレコード
ord-ae97ae3a24a248289ce6720d7deffdf4
出典データセット
uspto-grants-2009_06
特許番号
US07544697B2

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