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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 133079
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 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

Produkt 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]pyrazineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a23d649a3f17462bb850be2df7935785
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07390809B2

Notizen zur Reaktion

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