HCID 136009271, compound → HCID 136009214, compound

Participants

Reaction Steps

To a slurry of 20 wt % Pd(OH)2 on carbon (0.134 g, 0.192 mmol) in THF (20 mL) was added a solution of (E)-ethyl 2-((cis)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylidene)acetate (1.3 g, 3.83 mmol, Example #38, Step G) in THF (5 mL). The reaction mixture was sparged with hydrogen and an atmosphere of hydrogen was maintained via balloon. After about 3 days, the reaction mixture was filtered through Celite®, concd under reduced pressure and purified by flash chromatography on silica gel eluting with EtOAc to afford a dark brown/black solid. The compound was further by purified by chiral chromatography (Table 2, Method 47) to afford ethyl 2-((1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)acetate [W.1.1](Rt=12.0 min, or =negative) (0.400 g, 31%): LC/MS (Table 1, Method a) Rt=1.85 min; MS m/z: 342 (M+H)+ and ethyl 2-((1S,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)acetate [W.1.2](Rt=13.7 min, or =negative) (0.420 g, 32%) as a white solid: LC/MS (Table 1, Method a) Rt=1.85 min; MS m/z: 342 (M+H)+.

Provenance & Evidence