3-(4-Methylpiperazin-1-yl)aniline → N-Methyl-N-(3-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide

Participants

Reaction Steps

N-Methyl-N-(3-{2-[3-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide was prepared from N-[3-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-N-methyl-methanesulfonamide (75.0 mg, 0.214 mmol) and 3-(4-methylpiperazin-1-yl)aniline (45.0 mg, 0.235 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (24.0 mg, 0.0439 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.053 g, 49%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.43 (d, J=6.6 Hz, 1H), 8.05 (d, J=7.7 Hz, 1H), 7.93 (s, 1H), 7.60 (d, J=7.4 Hz, 1H), 7.52 (t, J=7.7 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.01 (d, J=8.0 Hz, 1H), 6.97 (t, J=7.2 Hz, 1H), 6.84 (s, 1H), 6.58 (dd, J=8.2, 1.5 Hz, 1H), 4.42 (s, 2H), 3.29-3.25 (m, 4H), 2.88 (s, 3H), 2.83 (s, 3H), 2.62-2.57 (m, 4H), 2.37 (s, 3H). MS=506 (MH)+.

Provenance & Evidence