6-(4-{[4-(2-oxo-2,3-Dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile → HCID 178518592, compound

Participants

Reaction Steps

A mixture of 6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (1-5; TFA salt) (71 mg, 0.1 mmol), 2M of NaN3 water solution (0.75 mL, 1.5 mmol), 2M of ZnBr2 water solution (0.5 mL, 1.0 mmol) was microwaved (Smith-Synthesizer) at 165° C. for 15 min. After this time, the solution was concentrated. The residue was re-dissolved in DMSO (1 mL) and purified by LCMS to afford the pure desired product (1-6; TFA salt) as a slightly yellow solid. Analytical LCMS: single peak (214 nm), 2.248 min. 1H NMR (500 MHz, DMSO-d6): δ 10.94 (s, 1H), 9.74-9.90 (s, 1H), 9.33 (d, J=2.1 Hz, 1H), 8.44 (d, J=2.1 Hz, 1H), 7.47-7.50 (s, 4H), 7.36-7.40 (m, 3H), 7.26-7.30 (m, 3H), 6.98-7.02 m, 3H), 4.45-4.54 (m, 1H), 4.33-4.38 (s, 2H), 3.49 (d, J=12.7 Hz, 2H), 3.13-3.23 (m, 2H), 2.58-2.69 (m, 2H), 1.95 (d, J=12.8 Hz, 2H); HRMS, calc'd for C31H29N8O (M+1), 529.2459; found 529.2449.

Provenance & Evidence