Hydrochloric Acid → 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone

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Reaction Steps

To a solution of 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.87 g, 8.72 mmol) in THF (30 mL), was added aqueous HCl (1N, 26.2 mL) at about 0° C. The ice bath was removed and the reaction was stirred at ambient temperature for about 6 h. THF was removed under reduced pressure. The aqueous phase was neutralized by the addition of saturated aqueous NaHCO3 and was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (60 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using 20 to 80% EtOAc in DCM to yield 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone (2.84 g, 81%) as a yellow amorphous solid. LC/MS (Table 1, Method a) Rt=2.44 min; MS m/z: 400 (M+H)+.

Provenance & Evidence