1,1'-Carbonyldiimidazole → HCID 136009246, compound

Participants

Reaction Steps

To a solution of 1-((cis)-4-ethylpyrrolidin-3-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine•hydrochloride (0.075 g, 0.168 mmol, Example #36, step F) in THF (1.00 mL) was added DIEA (0.150 mL, 0.861 mmol) and CDI (0.027 g, 0.168 mmol). After about 1 h, 4-aminomethyltetrahydropyran (0.020 g, 0.17 mmol, Acros) was added and the reaction mixture was stirred at ambient temperature for about 16 h. The reaction mixture was heated at about 55° C. for about 24 h. DMAP (0.021 g, 0.168 mmol) was added and continued stirring at about 55° C. for about 48 h. 4-aminomethyltetrahydropyran (0.400 g, 3.47 mmol, Acros) was added and continued stirring at about 55° C. for about 24 h. The solvent was removed under reduced pressure. The crude material was purified by RP-HPLC (Table 1, Method m) to afford (cis)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrrolidine-1-carboxamide (0.007 g, 10%) as product: LC/MS (Table 1, Method a) Rt=1.32 min; MS m/z: 398 (M+H)+.

Provenance & Evidence