4-Amino-1-Boc-piperidine → HCID 178521576, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-4-(5′-chloro-6-fluoro-2,4′-bipyridin-2′-yl-amino)cyclohexanol (15.5 mg, 0.048 mmol), DMSO (0.4 ml), and tert-butyl 4-aminopiperidine-1-carboxylate (48.2 mg, 0.241 mmol) reaction mixture was stirred at 105° C. for 40 hr. LCMS indicated formation of the intermediate tert-butyl 4-(5′-chloro-2′-(trans-4-hydroxycyclohexylamino)-2,4′-bipyridin-6-yl-amino)piperidine-1-carboxylate (LCMS (m/z): 502.4 (MH+), retention time=0.70 min.). The Boc protecting group was removed from the intermediate by adding HCL 6M aq (140 μl, 0.840 mmol) to the crude reaction mixture mixture, followed by stirring the mixture at 90° C. for 45 minutes. The reaction mixture was cooled, 0.5 ml of DMSO was added, filtered and purified by prep LC. Lypholization of the material yielded 9.8 mg of the title compound, as a TFA salt. LCMS (m/z): 402.3 (MH+), retention time=0.41 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 1.32-1.52 (m, 4 H) 1.71-1.87 (m, 2 H) 1.96-2.12 (m, 4 H) 2.27 (dd, J=14.21, 3.37 Hz, 2 H) 3.06-3.18 (m, 2 H) 3.39-3.50 (m, 2 H) 3.54-3.68 (m, 2 H) 4.05-4.17 (m, 1 H) 6.72 (d, J=8.50 Hz, 1 H) 6.90 (d, J=7.33 Hz, 1 H) 7.00 (s, 1 H) 7.56-7.64 (m, 1 H) 8.01 (s, 1 H)

Provenance & Evidence