Acetic Acid → 6-[1,2,3]Triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline

HRID 15996

Reaktionsgleichung

Reaktionsgleichung von HRID 15996
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.CC(O)=O.CCOC(C)=O.[H][H]>CO.[Pd]>[N:8]1([CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[C:6]2=[N:7][CH:2]=[CH:3][N:4]=[C:5]2[N:10]=[N:9]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 593419336-[1,2,3]Triazolo[4,5-b]pyrazin-1-ylmethyl-quinolineAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 6-(6-bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinoline (200 mg, 0.586 mmol) in MeOH (10 mL):AcOH (1 mL): EtOAc (1 mL) was degassed 3 times with nitrogen. To this solution was added Pd/C (20 mg). A balloon containing hydrogen was added via syringe and the reaction was allowed to stir for 18 hours at room temperature. The reaction did not complete and more Pd/C was added (20 mg) and stirred for 18 hours at room temperature. The reaction was stopped when LCMS showed a ratio of 1:1 (product:starting material). The reaction was filtered over celite and washed with EtOAc (50 mL). The filtered solution was concentrated and purified by Biotage silica gel column chromatography with EtOAc: Hexanes to give 30 mg of the product 6-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline (20% yield).

Aufarbeitung

  1. additionwas added via syringe
  2. stirringstirred for 18 hours at room temperature
  3. filtrationThe reaction was filtered over celite
  4. washwashed with EtOAc (50 mL)
  5. concentrationThe filtered solution was concentrated
  6. custompurified by Biotage silica gel column chromatography with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-4825ae5a95894914b5d5be85049a19ca
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732604B2

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