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Cyanogen Bromide → 5-(4-{1,2-Dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}phenyl)-1,3,4-oxadiazol-2-amine

HRID 1025810
ノート
印刷プレビュー

反応式

HRID 1025810 の反応式
O.[NH2:2][NH2:3].[CH3:4][C:5]([C:25]1[CH:34]=[CH:33][C:28]([C:29](OC)=[O:30])=[CH:27][CH:26]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH3:17])=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+].[N:40]#[C:41]Br>C(O)C.O1CCOCC1.O>[CH3:4][C:5]([C:25]1[CH:26]=[CH:27][C:28]([C:29]2[O:30][C:41]([NH2:40])=[N:3][N:2]=2)=[CH:33][CH:34]=1)([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]([CH3:17])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH3:24])=[CH:13][CH:14]=1)[CH:6]([CH3:8])[CH3:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10476Cyanogen BromideHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium Bicarbonate2 回HCID 59026736Methyl 4-{1,2-dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}benzoate2 回

生成物 1

HCID 583812355-(4-{1,2-Dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}phenyl)-1,3,4-oxadiazol-2-amine

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

Hydrazine monohydrate (10 equiv.) is added to a stirred solution of 5g (1 equiv.) in ethanol and the resulting solution heated at reflux until 5g is consumed. After cooling to room temperature, the volatiles are removed in vacuo, and the residue is partitioned between EtOAc and water. The organic phase is separated, washed three times with water, brine, dried (MgSO4) and concentrated in vacuo. The crude residue is dissolved in dioxane to which aqueous sodium bicarbonate (1.1 equiv) in water is added dropwise via syringe. A solution of cyanogen bromide (1.1 equiv.) in dioxane is then added slowly, and the resulting mixture is aged at ambient temperature until the reaction is deemed complete. The reaction mixture is poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5h. If desired, 5h can be resolved into its enantiomeric components using preparative chiral HPLC techniques.

後処理

  1. temperaturethe resulting solution heated
  2. customis consumed
  3. customthe volatiles are removed in vacuo
  4. customthe residue is partitioned between EtOAc and water
  5. customThe organic phase is separated
  6. washwashed three times with water, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. additionis added dropwise via syringe
  10. customis aged at ambient temperature until the reaction
  11. extractionextracted three times with EtOAc
  12. washThe combined organic extracts are washed with brine
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated in vacuo
  15. customPurification of the crude residue by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-57d36fc2316b482795a533dbe76d6aa2
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729104B2

反応ノート

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