6-Chloro-3-pyridinecarbonitrile → 6-((1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylamino)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a microwave vessel was added (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride (0.0979 g, 0.311 mmol, Example #6, Step C), EtOH (2 mL), 6-chloronicotinonitrile (0.057 g, 0.41 mmol), and TEA (0.130 mL, 0.932 mmol). The reaction mixture was heated in a CEM™ microwave at about 130° C. for about 1 h (250 psi maximum pressure, 5 min maximum ramp, 300 maximum watts). After cooling to ambient temperature, the reaction was concentrated under reduced pressure and purified by silica gel chromatography eluting with DCM/MeOH/Et2NH (970:27:3) to give 6-((1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylamino)nicotinonitrile (0.027 g, 25%): LC/MS (Table 2, Method a) Rt=1.24 min; MS m/z: 345(M+H)+.

Provenance & Evidence