4-Diazo-4H-imidazole-5-carboxamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098284
[Si:1]([O:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:14](=[C:16]1[N:20]=[CH:19][N:18]=[C:17]1[C:21]([NH2:23])=[O:22])=[N-:15]>CS(C)=O>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:12](=[O:13])[N:20]2[CH:19]=[N:18][C:17]([C:21]([NH2:23])=[O:22])=[C:16]2[N:14]=[N:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 534265854-Diazo-4H-imidazole-5-carboxamideHCID 595674552-(Tert-butyldimethylsilyloxy)ethyl isocyanate

Produkt 1

HCID 441288053-(2-(tert-Butyldimethylsilyloxy)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Crude 2-(tert-butyldimethylsilyloxy)ethyl isocyanate (422 mg, 2.097 mmol) was added drop wise to a solution of 5-diazoimidazole-4-carboxamide (250 mg, 1.823 mmol) in dimethylsulfoxide (2.5 mL) and the reaction mixture was stirred at room temperature. After 16 hours, the crude reaction mixture was applied to reverse phase silica (C18 silica) and eluted with water and then acetonitrile. The acetonitrile fractions were combined and purified by flash column chromatography (SiO2, gradient 0-100% acetonitrile in dichloromethane) to furnish the title compound as a white solid. Yield: 40 mg, 0.12 mmol, 6.5%. LCMS (ES+) m/z 339 (M+H)+ at 3.19 minutes. 1H NMR (400 MHz, d6-DMSO) δ: 8.87 (1H, s), 7.83 (1H, br s), 7.70 (1H, bs), 4.41 (2H, t), 3.98 (2H, t), 0.78 (9H, t), −0.03 (6H, s).

Aufarbeitung

  1. customthe crude reaction mixture
  2. washeluted with water
  3. custompurified by flash column chromatography (SiO2, gradient 0-100% acetonitrile in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-60ee976f646b447eabde9485ee76fe53
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450479B2

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