2-[-2-(5,8-Dimethyl[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole → US8796304, 2-[2-(5,8-Bis(trideuteromethyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-5,5-dideutero-5H-imidazo[2,1-a]isoindole

HRID 2401522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401522
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH:11]=[CH:12][C:13]3[N:14]=[C:15]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH2:17][N:16]4[CH:24]=3)[N:10]=[C:6]2[C:5]([CH3:25])=[N:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[C:15]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH2:17][N:16]4[CH:24]=3)[N:10]=[C:6]2[C:5]([CH3:25])=[N:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 696708672-[-2-(5,8-Dimethyl[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole

Produkt 1

HCID 57331250US8796304, 2-[2-(5,8-Bis(trideuteromethyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-5,5-dideutero-5H-imidazo[2,1-a]isoindoleAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-[-2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole (139 mg, 0.423 mmol) in methanol (100 mL) was added 10% palladium on carbon (27 mg). A current of hydrogen gas was bubbled through, and the reaction was kept under an atmosphere of hydrogen overnight with stirring. After filtration the organics were evaporated onto silica gel (2 g). Chromatography (gradient elution; A:B 100:0 to 0:100, where A is ethyl acetate and B is 10% MeOH in ethyl acetate) afforded the title compound as a white solid (50.6 mg, 36%). 1H NMR (500 MHz, CDCl3): δ 7.86-7.82 (m, 2H), 7.46-7.42 (m, 2H), 7.33 (t, J=7.5 Hz, 1H), 7.02 (s, 1H), 4.84 (s, 2H), 3.44 (dd, J=8.9, 6.6 Hz, 2H), 3.33 (dd, J=8.9, 6.6 Hz, 2H), 2.91 (s, 3H), 2.73 (s, 3H). LC-MS: m/z=331.0 (MH+), tR=0.74 minutes.

Aufarbeitung

  1. customA current of hydrogen gas was bubbled through, and the reaction
  2. filtrationAfter filtration the
  3. customorganics were evaporated onto silica gel (2 g)
  4. washChromatography (gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-998a29e4d6b94e43bd4b134c9e65736a
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796304B2

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