Reaction Steps
4-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-N,N-dimethyl-benzenesulfonamide was prepared from 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (150.0 mg, 0.7041 mmol) and N,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (210.0 mg, 0.6748 mmol) in a manner analogous to Step 2c. The reaction product was isolated as a tan solid (0.074 g, 34%). MP=188-190° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.63 (d, J=6.4 Hz, 1H), 8.38 (d, J=8.2 Hz, 2H), 7.88-7.82 (m, 3H), 7.03 (t, J=6.8 Hz, 1H), 6.21 (br s, 2H), 2.66 (s, 6H). MS=318 (MH)+. 54b) N,N-Dimethyl-4-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzenesulfonamide was prepared from 4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-N,N-dimethyl-benzenesulfonamide (75.0 mg, 0.236 mmol) and 1-(4-bromo-phenyl)-4-methyl-piperazine (75.0 mg, 0.294 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (48.0 mg, 0.0878 mmol) as the ligand in a manner analogous to Step 2d. The title compound was isolated as a yellow foam (0.034 g, 29%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.45 (d, J=6.7 Hz, 1H), 8.22 (d, J=8.1 Hz, 2H), 7.91 (d, J=7.8 Hz, 2H), 7.63 (d, J=6.3 Hz, 1H), 7.49 (d, J=7.8 Hz, 2H), 7.00-6.95 (m, 3H), 6.69 (s, 1H), 3.20-3.15 (m, 4H), 2.78 (s, 6H), 2.63-2.58 (m, 4H), 2.36 (s, 3H). MS=492 (MH)+.
