Lithium hydroxide, monohydrate → 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one

HRID 445982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445982
FC(F)(F)C([NH:5][CH:6]([CH2:17][C:18](=[O:32])[N:19]1[CH2:24][CH2:23][N:22]2[C:25]([C:28]([F:31])([F:30])[F:29])=[N:26][N:27]=[C:21]2[CH2:20]1)[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16])=O.O.[OH-].[Li+]>CO.O>[O:32]=[C:18]([N:19]1[CH2:24][CH2:23][N:22]2[C:25]([C:28]([F:31])([F:30])[F:29])=[N:26][N:27]=[C:21]2[CH2:20]1)[CH2:17][CH:6]([NH2:5])[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86657327N-trifluoroacetyl-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine

Produkt 1

HCID 113066913-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-oneAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

In a 25 mL three neck flask (2S) N-trifluoroacetyl-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (wt.-0.250 g, % Purity by HPLC-96.5%) was dissolved in a mixture of MeOH (2.5 mL) and water (0.5 mL) at 25-30° C. To the reaction mixture lithium hydroxide monohydrate (21 mg) was added. It was stirred at 0 to 5° C. for 4 h and at 25 to 30° C. for 24 h. Distilled out solvent at reduced pressure on Buchi rotavapour. To the thick liquid water (2.5 mL) was added. It was transferred into a separating funnel. It was extracted twice with ethyl acetate. Both the extracts were combined and washed with water and brine solution. It was dried over anhydrous sodium sulfate. Distilled out solvent to obtain a 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (Wt.-78 mg, % Purity by HPLC-83.1%).

Aufarbeitung

  1. distillationDistilled out solvent at reduced pressure on Buchi rotavapour
  2. additionTo the thick liquid water (2.5 mL) was added
  3. customIt was transferred into a separating funnel
  4. extractionIt was extracted twice with ethyl acetate
  5. washwashed with water and brine solution
  6. dry with materialIt was dried over anhydrous sodium sulfate
  7. distillationDistilled out solvent

Quellen und Nachweise

ORD-Eintrag
ord-61728403a3924598955e172fda355509
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476437B2

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