HCID 58923890, compound → HCID 136353475, compound

Participants

Reaction Steps

3-(Benzyloxy)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine, (3.34 g, 10.0 mmol) prepared as described in Example 368, was dissolved in a mixture of methanol (100 mL) and dichloromethane (100 mL) and transferred to a hydrogenation vessel charged with 10% palladium on carbon (5 g, 47 mmol). The vessel was placed under hydrogen pressure (50 psi, 3.45×105 Pa) and shaken for two days at ambient temperature. An analysis by LC/MS indicated the presence of starting material. The catalyst was removed by filtration through a layer of CELITE filter aid, and the filtrate was placed under hydrogen pressure (50 psi, 3.45×105 Pa) again for two days in the presence of 10% palladium on carbon (5 g, 47 mmol). The catalyst was removed by filtration through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure. The residue (560 mg) was combined with material from another run to provide 1.19 g of 6-amino-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-3-ol.

Provenance & Evidence