Acetonitrile → HCID 118195206, compound

Participants

Reaction Conditions

Reaction Steps

(R)-2′-Chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5′-fluoro-2-(3-hydroxypyrrolidin-1-yl)-[3,3′-bipyridine]-5-carboxamide (Example 288, 100 mg, 0.195 mmol), Pd(Ph3P)4 (22.51 mg, 0.019 mmol), zinc cyanide (114 mg, 0.974 mmol) were added to a vial, flushed with argon, treated with DMF (2 mL) and stirred for 18 h at 130° C. The solvent was evaporated off under reduced pressure and the residue was purified by preparative SFC (Column NH2, from 16% to 21% in 6 min). The fractions containing product were combined and the solvent was evaporated off under reduced pressure to give a residue which was lyophilized in water/min. vol. MeCN to afford the title product as an off-white powder. UPLC-MS (Condition 3), tR=1.09 min, m/z=504.1/506.1 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 1.70-1.97 (m, 2H) 2.80-2.94 (m, 1H) 3.09-3.23 (m, 1H) 3.23-3.38 (m, 2H) 4.16-4.29 (m, 1H) 4.85-5.02 (m, 1H) 7.35 (d, J=8.47 Hz, 2H) 7.86 (d, J=8.28 Hz, 2H) 8.08-8.37 (m, 2H) 8.86 (d, J=6.96 Hz, 2H) 10.24 (br. s, 1H).

Provenance & Evidence