Carbon Dioxide → Rizatriptan

HRID 1180100

反応式

HRID 1180100 の反応式
O[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)[CH:11]=2)[NH:6][C:5]=1C(O)=O.C(=O)=O.C(O)(=O)CCC(O)=O.[N:33]1[C:42]2C(=CC=CC=2)C=C[CH:34]=1>>[CH3:34][N:33]([CH2:2][CH2:3][C:4]1[C:12]2[CH:11]=[C:10]([CH2:13][N:14]3[N:15]=[CH:16][N:17]=[CH:18]3)[CH:9]=[CH:8][C:7]=2[NH:6][CH:5]=1)[CH3:42]

参加物

5

反応物 4

HCID 280Carbon DioxideHCID 1110Succinic AcidHCID 7047QuinolineHCID 103566433-(2-Hydroxyethyl)-5-[1,2,4]triazol-1-ylmethyl-1h-indol-2-carboxylic acid

生成物 1

HCID 5078Rizatriptan収率 86%

実験手順

700 mg (2,2 mmoles) of 3-(2-hydroxyethyl)-5-[1,2,4-triazol-1-ylmethyl]-1H-indol-2-carboxylic acid was suspended in 7 ml of dry quinoline. 14 mg of cuprous oxide was added and the stirred suspension heated, under dry nitrogen stream, to 200° C. The reaction mixture was kept at this temperature until no more CO2 was released (15-20 min.). It was left to cool to room temperature and the reaction mixture was filtered through decalite. The filtrate was concentrated by vacuum distillation of the solvent, providing a residue which was dissolved with a succinic acid solution and washed three times with 10 ml of dichloromethane. The washed aqueous phase was cooled and adjusted to pH 12 with a 40% sodium hydroxide solution and extracted three times with 20 ml of dichloromethane. The combined organic phases were dried on anhydrous sodium sulphate and evaporated to dryness. The residue was recrystallised from heptane/isopropyl acetate to give 510 mg (86%) of rizatriptan as a white solid.

後処理

  1. temperaturethe stirred suspension heated, under dry nitrogen
  2. customstream, to 200° C
  3. custom(15-20 min.)
  4. waitIt was left
  5. filtrationthe reaction mixture was filtered through decalite
  6. concentrationThe filtrate was concentrated by vacuum distillation of the solvent
  7. customproviding a residue which
  8. washwashed three times with 10 ml of dichloromethane
  9. temperatureThe washed aqueous phase was cooled
  10. extractionextracted three times with 20 ml of dichloromethane
  11. dry with materialThe combined organic phases were dried on anhydrous sodium sulphate
  12. customevaporated to dryness
  13. customThe residue was recrystallised from heptane/isopropyl acetate

出典と根拠

ORDレコード
ord-b12dfa9dc83d4aaca8b80b4a944176b0
出典データセット
uspto-grants-2007_10
特許番号
US07279581B2

関連ノート

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