Hydrochloric Acid → HCID 178482965, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(5-chloro-2-fluoropyridin-4-yl)-N-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (15 mg, 0.045 mmol), DMSO (0.4 ml), and tert-butyl(trans-4-aminocyclohexyl)methylcarbamate (92 mg, 0.401 mmol) was stirred at 100-105° C. for 18 hours, and the reaction progress was followed by LCMS. To the crude intermediate was added 6 M aq.HCl (120 μl, 0.720 mmol) and heated at 80° C. for 40 minutes, and the reaction progress was followed by LCMS. The reaction mixture was let cool, added 0.5 ml of DMSO, filtered and purified by prep LC. After lypohilization, 15.6 mg of the title compound, as a TFA salt was obtained. LCMS (m/z): 445.2 (MH+), retention time=0.59 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 1.12-1.47 (m, 6H) 1.59 (d, J=12.60 Hz, 2H) 1.67 (ddd, J=7.18, 3.81, 3.66 Hz, 1H) 1.92 (d, J=12.31 Hz, 2H) 2.01-2.11 (m, 1H) 2.16 (d, J=11.43 Hz, 2H) 2.83 (d, J=7.03 Hz, 2H) 3.17 (s, 3H) 3.33-3.45 (m, 2H) 3.56 (d, J=7.33 Hz, 2H) 3.60-3.72 (m, 1H) 3.93 (dd, J=11.14, 2.93 Hz, 2H) 6.92 (s, 1H) 8.02 (d, J=2.64 Hz, 2H) 8.11 (s, 1H).

Provenance & Evidence