Sodium Carbonate → HCID 178495955, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N2′-(trans-4-aminocyclohexyl)-5′-chloro-3-fluoro-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine trifluoroacetate (30 mg, 0.055 mmol) and sodium carbonate (23 mg, 0.22 mmol) in DMSO (0.75 ml) was added p-toluenesulfonic acid 2-methoxyethyl ester (15 mg, 0.066 mmol). The mixture was stirred at 85° C. for 20 hr in a sealed microwave vial. The cooled reaction mixture was filtered. The filtrate was purified by reverse phase HPLC and lyophilized to give 5.0 mg of 5′-chloro-3-fluoro-N2′-(trans-4-(2-methoxyethylamino)cyclohexyl)-N6-((tetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine as its TFA salt. LCMS (m/z): 492.2 (MH+), retention time=0.57 min.; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.10-1.46 (m, 6 H) 1.64-1.74 (m, 2 H) 1.86 (br. s., 2 H) 1.95-2.09 (m, 2 H) 2.09-2.26 (m, 2 H) 2.58 (br. s., 1 H) 2.88 (t, J=5.09 Hz, 2 H) 3.17 (t, J=6.26 Hz, 2 H) 3.29-3.45 (m, 5 H) 3.53 (t, J=5.09 Hz, 3 H) 4.00 (dd, J=11.35, 3.52 Hz, 2 H) 4.34-4.47 (m, 1 H) 4.54-4.68 (m, 1 H) 6.35-6.48 (m, 2 H) 7.31 (t, J=8.80 Hz, 1 H) 8.11 (s, 1 H).

Provenance & Evidence