Sodium sulfate decahydrate → 5-(N-[ethyl]amino)-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

HRID 1075566ノート

反応式

HRID 1075566 の反応式
[C:1]([NH:4][C:5]1[N:10]=[C:9]2[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([NH:4][C:5]1[N:10]=[C:9]2[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:12][NH:13][C:8]2=[CH:7][CH:6]=1)[CH3:2]

参加物

5

反応物 3

HCID 62649Sodium sulfate decahydrateHCID 10445946N-[3-(1-Methylpiperidin-4-YL)-1H-pyrrolo[3,2-B]pyridin-5-YL]acetamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 102207875-(N-[ethyl]amino)-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

A mixture of 0.200 gm (0.74 mMol) 5-(N-[acetyl]amino)-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine and 0.125 gm (3.31 mMol) lithium aluminum hydride in 40 mL tetrahydrofuran was heated at 75° C. for 18 hours. The reaction mixture was cooled to 0° C. and was then treated with sodium sulfate decahydrate. After vigorous stirring the reaction mixture was filtered through a pad of celite and the filtrate concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing from 0-20% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.10 gm (54%) of the title compound.

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationwas filtered through a pad of celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washeluting with dichloromethane containing from 0-20% methanol
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e99780d1b0c04ec2b542f4afb21097d4
出典データセット
uspto-grants-1999_05
特許番号
US05905084

反応ノート

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