Example 35
A mixture of 6-chloro-4-((2-methoxy-5-(methoxymethyl)-3-(2-methyl-2H-1,2,3-triazol-4-yl)phenyl)amino)-N-(methyl-d3)pyridazine-3-carboxamide (25 mg, 0.059 mmol), cyclopropanecarboxamide (25.3 mg, 0.297 mmol), Pd2(dba)3, chloroform adduct (6.14 mg, 5.94 μmol), xantphos (6.87 mg, 0.012 mmol) and Cs2CO3 (77 mg, 0.238 mmol) in dioxane (0.5 mL) was degassed by bubbling N2 through the mixture for 5 minutes. The reaction vessel was sealed and heated to 130° C. for 30 minutes. The reaction mixture was diluted with DMSO, filtered and purified by prep. HPLC. The purfractions were concentrated to afford 6-(cyclopropane-carboxamido)-4-((2-methoxy-5-(methoxymethyl)-3-(2-methyl-2H-1,2,3-triazol-4-yl)phenyl)amino)-N-(methyl-d3)pyridazine-3-carboxamide (16.3 mg; 57.7%). MS (M+1) m/z: 470.0 (M+H)+. LC retention time 1.46 [I]. 1H NMR (500 MHz, DMSO-d6) δ 11.29 (s, 1H), 10.95 (s, 1H), 9.13 (s, 1H), 8.10 (d, J=9.0 Hz, 2H), 7.67 (d, J=1.8 Hz, 1H), 7.39 (d, J=1.7 Hz, 1H), 4.42 (s, 2H), 4.23 (s, 3H), 3.64 (s, 3H), 3.30 (s, 3H), 2.14-2.00 (m, 1H), 0.87-0.73 (m, 4H).
