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1H-1,2,4-Triazole → 7-N-(tert-Butoxycarbonyl)-8-([1,2,4]triazol-4-ylmethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

HRID 133079
ノート
印刷プレビュー

反応式

HRID 133079 の反応式
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]2[N:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[N:27]=[C:21]2[CH:20]1[CH2:32]OS(C)(=O)=O)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]2[N:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[N:27]=[C:21]2[CH:20]1[CH2:32][N:4]1[CH:3]=[N:2][N:1]=[CH:5]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]
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

5

反応物 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 877981657-N-(tert-Butoxycarbonyl)-8-(methanesulfonyloxymethyl)-2-(trifluoromethyl) 5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

生成物 1

HCID 693628917-N-(tert-Butoxycarbonyl)-8-([1,2,4]triazol-4-ylmethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine収率 63%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
50 °C

実験手順

To a solution of 47 mg (0.683 mmol) of [1,2,4]triazole in 1.0 mL of DMF was added 189 mg (1.365 mmol) of potassium carbonate. The mixture was heated at 50° C. for 15 min. To this was added 182 mg (0.455 mmol) of 7-N-(tert-butoxycarbonyl)-8-(methanesulfonyloxymethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine. The mixture was stirred at 50° C. for 14 h. DMF was removed in vacuo and the residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with three portions of ethyl acetate. The combined organics were dried over magnesium sulfate and concentrated to give 107 mg of an orange oil. The mixture was eluted on a preparative TLC plate (silica gel, 50% ethyl acetate/hexane). The plate was scraped and the product eluted from the silica gel with 80:15:1 chloroform/methanol/ammonium hydroxide to give the title compound.

後処理

  1. customDMF was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with three portions of ethyl acetate
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-a23d649a3f17462bb850be2df7935785
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07390809B2

反応ノート

読み込み中…

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