6-Chloro-3-pyridinecarbonitrile → 6-{4-[(4-Cyclobutylhexahydro-1H-1,4-diazepin-1-yl)carbonyl]phenyl}-3-cyanopyridine hydrochloride

Participants

Reaction Steps

The title compound (E12) was prepared in a similar manner to Example 11 from 1-cyclobutyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}hexahydro-1H-1,4-diazepine (D7) (0.15 g) and 6-chloronicotinonitrile (0.054 g). The crude reaction mixture was purified by flash chromatography [silica gel, step gradient 0-15% MeOH (containing 10% 0.88 ammonia solution) in DCM]. The free base compound was converted into the HCl salt in dry DCM (2 ml) with ethereal HCl (1 ml), 1N). Evaporation of solvent afforded the title compound (E12) as a white solid (0.046 g). 1H NMR δ (methanol-d4): 1.78-1.90 (2H, m), 2.1-2.4 (6H, m), 3.03-3.2 (2H, m), 3.5-3.9 (6H, m), 4.28-4.35 (1H, m), 7.65 (2H, d, J=8 Hz), 8.13 (1H, d, J=8 Hz), 8.23-8.26 (3H, m), 8.99 (1H, d, J=2.4 Hz). LCMS electrospray (+ve) 361 (MH+).

Provenance & Evidence