Methanol → 1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

HRID 2203351ノート

反応式

HRID 2203351 の反応式
C[Al](C)C.[Cl-].[NH4+:6].[F:7][C:8]([F:26])([C:22]([F:25])([F:24])[F:23])[CH2:9][CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([C:20]#[N:21])=[N:12]1.CO>C1(C)C=CC=CC=1>[F:26][C:8]([F:7])([C:22]([F:23])([F:24])[F:25])[CH2:9][CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([C:20](=[NH:6])[NH2:21])=[N:12]1

参加物

6

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 866789821-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

生成物 1

HCID 866789831-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

Trimethylaluminum (2.0M in toluene, 60 mL, 120 mmol) was added dropwise to a suspension of ammonium chloride (6.42 g, 120 mmol) in 180 mL toluene cooled to 0° C. The solution was then stirred at room temperature for 3.5 hours. This solution (0.5M, 146 mL, 72.9 mmol) was then added to the intermediate from Step D above (4.6 g, 15.9 mmol) and then heated at 110° C. for 2.5 hours. The solution was then cooled to room temperature and carefully poured to silica gel (70 g) and methanol (750 mL). After stirring overnight the suspension was filtered and the filtered solid washed with methanol. The filtrate was concentrated in vacuo to give the title compound which was used in the next step without further purification. m/z=308.2 (M+H).

後処理

  1. temperatureheated at 110° C. for 2.5 hours
  2. temperatureThe solution was then cooled to room temperature
  3. stirringAfter stirring overnight the suspension
  4. filtrationwas filtered
  5. washthe filtered solid washed with methanol
  6. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-f02e5e12e95941b581d2189fc37f0c60
出典データセット
uspto-grants-2016_06
特許番号
US09365574B2

反応ノート

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