Cyanide → HCID 86757583、化合物

HRID 429044

反応式

HRID 429044 の反応式
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12.[C-:18]#[N:19].[Na+].[C-]#N>CN(C=O)C.C(O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:18]([C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12)#[N:19]

参加物

8

反応物 3

HCID 5975CyanideHCID 8929Sodium Cyanide2 回HCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

生成物 1

HCID 86757583HCID 86757583、化合物収率 40%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (10.0 g, 39.5 mmol) in DMF (50 mL) and ethanol (10 mL) was added either sodium cyanide (3.9 g, 80.0 mmol) or tetrabutylarimonium cyanide (11.8 g, 1.1 eq) or tetrabutylammonium chloride (14.7 g, 1.0 eq) and sodium cyanide (2.4 g, 1.2 eq) together. This solution or suspension was warmed up to 60° C. until reaction was completed as judged by TLC. The reaction mixture was then diluted with water (200 mL) and stirred gently at rt for 10 min. A large amount of precipitate formed. The solid was filtered and rinsed thoroughly with water to afford the title compound as an off-white solid after drying: 40-80% yield. This material was >95% pure as judged by HPLC and was used directly without further purification.

後処理

  1. customA large amount of precipitate formed
  2. filtrationThe solid was filtered
  3. washrinsed thoroughly with water

出典と根拠

ORDレコード
ord-f29d4bde23a8479e8594b6e02fd39747
出典データセット
uspto-grants-2001_11
特許番号
US06316438B1

関連ノート

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