反应详情

N-(6-Bromo-2-pyridinyl)-N′-carboethoxy-thiourea was prepared from 6-bromo-pyridin-2-ylamine (1.0 g, 5.8 mmol) in a manner analogous to Step 2a. The product of the reaction was isolated as a yellow solid. 1H NMR (400 MHz, CDCl3, δ, ppm): 12.03 (br s, 1H), 8.81 (d, J=8.0 Hz, 1H), 8.06 (br s, 1H), 7.60 (t, J=8.0 Hz, 1H), 7.32 (d, J=7.7 Hz, 1H), 4.31 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.2 Hz, 3H). MS=306 (MH)+. 12b) 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from N-(6-bromo-2-pyridinyl)-N′-carboethoxy-thiourea (1.8 g, 5.9 mmol) in a manner analogous to Step 2b. The product was isolated as an off-white solid (0.71 g, 56%). MP=203-205° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 7.40-7.32 (m, 2H), 7.23-7.20 (m, 1H), 6.26 (br s, 2H). MS=215 (MH)+. 12c) [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-yl-phenyl)-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100.0 mg, 0.3468 mmol) and 4-(4-bromo-phenyl)-morpholine (101.0 mg, 0.4172 mmol) in a manner analogous to Step 2d. The title compound was isolated as a yellow solid (0.018 g, 12%). MP=247-249° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.28-8.24 (m, 2H), 8.15-8.11 (m, 2H), 7.55-7.51 (m, 2H), 7.49-7.44 (m, 2H), 7.04-7.01 (m, 1H), 6.96-6.91 (m, 2H), 6.68 (s, 1H), 3.90-3.85 (m, 4H), 3.15 (s, 3H), 3.14-3.10 (m, 4H). MS=450 (MH)+.