Dimethylformamide → 6-(5-chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione

HRID 1876773ノート

反応式

HRID 1876773 の反応式
Cl[C:2]1[CH:3]=C[C:5]([C:8]2[C:9]([C:17]([OH:19])=O)=[N:10][CH:11]=[C:12](C(=O)N)[N:13]=2)=[N:6][CH:7]=1.[CH3:20][N:21](C)C=O.S(Cl)(Cl)=[O:26].Cl[CH2:30][Cl:31]>>[Cl:31][C:30]1[CH:3]=[CH:2][C:7]([N:6]2[C:5](=[O:26])[C:8]3[C:9](=[N:10][CH:11]=[CH:12][N:13]=3)[C:17]2=[O:19])=[N:21][CH:20]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 68555708HCID 68555708、化合物

生成物 1

HCID 64519736-(5-chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione

反応条件

温度
27.5 °C

実験手順

3-(5-Chloropyridin-2-yl)-carbamoylpyrazine-2-carboxylic acid (100 g) was suspended in 500 ml dichloromethane. The suspension was refluxed azeotropically for 60 min. The mixture was cooled to 25-30° C. and dimethyl formamide (2.6 gm) was added followed by addition of thionyl chloride (72 g) in 45-60 min at 25-30° C. The resulting mixture was refluxed till completion of reaction. The reaction mixture was concentrated to dryness at atmospheric pressure. Cooled the solid to 20-25° C. and 500 ml chilled water was added Cooled the slurry to 20-25° C. and stirred for 30 min. Slurry was filtered and washed with 200 ml water. The solid was dried at 60-70° C. to obtain 88 g of title compound.

後処理

  1. temperatureThe suspension was refluxed azeotropically for 60 min
  2. temperatureThe resulting mixture was refluxed till completion of reaction
  3. concentrationThe reaction mixture was concentrated to dryness at atmospheric pressure
  4. temperatureCooled the solid to 20-25° C.
  5. temperature500 ml chilled water
  6. additionwas added
  7. temperatureCooled the slurry to 20-25° C.
  8. filtrationSlurry was filtered
  9. washwashed with 200 ml water
  10. customThe solid was dried at 60-70° C.

出典と根拠

ORDレコード
ord-1c9ab743bcea4405bdf7d80cc1186b9e
出典データセット
uspto-grants-2012_11
特許番号
US08309723B2

反応ノート

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