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1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine → 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1969883
ノート
印刷プレビュー

反応式

HRID 1969883 の反応式
[CH2:1]([CH:3]1[CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][N:21](S(C4C=CC(C)=CC=4)(=O)=O)[C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2]>O1CCOCC1.[OH-].[Na+]>[CH2:1]([CH:3]1[CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][NH:21][C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 585572181-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

生成物 1

HCID 1360092531-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine収率 88.1%

試薬・触媒・溶媒 2

HCID 14798Sodium Hydroxide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

To the solution of 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.76 g, 8.04 mmol) in 1,4-dioxane (55 mL), aqueous sodium hydroxide solution (2N, 12 mL) was added and the reaction mixture was heated at about 60° C. for about 90 min. The solvent was removed and the residue partitioned between saturated solution of ammonium chloride in water and EtOAc (75 mL each). The aqueous phase was further washed with EtOAc (60 mL); the combined organic extracts were washed with brine (65 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to yield a brown solid. The solid was triturated in ether (20 mL) and the precipitate was collected by filtration and dried to yield 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (2.22 g, 88%) as a beige solid. LC/MS (Table 1, Method a) Rt=1.71 min; MS m/z: 314 (M+H)+.

後処理

  1. customThe solvent was removed
  2. customthe residue partitioned between saturated solution of ammonium chloride in water and EtOAc (75 mL each)
  3. washThe aqueous phase was further washed with EtOAc (60 mL)
  4. washthe combined organic extracts were washed with brine (65 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown solid
  9. customThe solid was triturated in ether (20 mL)
  10. filtrationthe precipitate was collected by filtration
  11. customdried

出典と根拠

ORDレコード
ord-e236737de73943899a7656d037f8d8ea
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426411B2

反応ノート

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