反应详情

3-Methanesulfonyl-benzylamine was prepared from 3-methanesulfonyl-benzonitrile (0.984 g, 5.43 mmol) in a manner analogous to Example 156b. Product isolated as a pale yellow oil (0.946 g, 94%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.93 (s, 1H), 7.83 (d, J=7.7 Hz, 1H), 7.64 (d, J=7.6 Hz, 1H), 7.54 (t, J=7.7 Hz, 1H), 4.00 (s, 2H), 3.06 (s, 3H). MS=186 (MH)+. 160 b) (2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methanesulfonyl-benzyl)-amine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (500.0 mg, 2.151 mmol) and 3-methanesulfonyl-benzylamine (450.0 mg, 2.429 mmol) in a manner analogous to Example 2d. Product isolated as a pale yellow solid (0.429 g, 59%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.97 (s, 1H), 7.93-7.87 (m, 2H), 7.68 (d, J=7.7 Hz, 1H), 7.58 (t, J=7.7 Hz, 1H), 6.85 (t, J=7.4 Hz, 1H), 6.35 (d, J=7.8 Hz, 1H), 5.51-5.44 (m, 1H), 4.59 (d, J=5.8 Hz, 2H), 3.07 (s, 3H). MS=337, 339 (MH)+. 160 c) N(8)-(3-Methanesulfonyl-benzyl)-N(2)-[4-(4-methyl-piperazin-1-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from (2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-(3-methanesulfonyl-benzyl)-amine (75.0 mg, 0.223 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (47.0 mg, 0.246 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (23.0 mg, 0.0421 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a brown lyophilate as the trifluoroacetic acid salt (0.004 g, 4%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.50 (br s, 1H), 9.17 (s, 1H), 7.98-7.93 (m, 2H), 7.81 (d, J=8.0 Hz, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.65-7.59 (m, 3H), 6.96 (d, J=8.9 Hz, 2H), 6.70 (t, J=7.5 Hz, 1H), 6.64 (br s, 1H), 6.32 (d, J=7.6 Hz, 1H), 4.65-4.60 (m, 2H), 3.72-3.65 (m, 2H), 3.23-3.13 (m, 6H), 2.92-2.82 (m, 6H). MS=492 (MH)+.