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 2175360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175360
[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-7e189e8221244252bd22b071d3618292
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062060B2

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