Medical application of N-{5-(1,2,4-triazole-1-yl) thiazole-2-yl} fatty acid amide
The technology of a kind of fatty amide, thiazole is applied in the application field in the preparation of influenza virus neuraminidase inhibitor
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Embodiment 1
[0007] N Preparation of -[4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]acetamide
[0008] 2 mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine, 6.0 mL of acetic anhydride, reacted at 50°C for 1.5 h, after cooling, poured into ice water and stirred to obtain N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]acetamide, the yield is 90.6%, m.p. 190~191℃. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.13 (s, 9H, 3×CH 3 ), 2.29 (s, 3H, CH 3 ), 8.12 (s, 1H, C 2 N 3 H 2 3-H), 8.28 (s, 1H, C 2 N 3 H 2 5-H), 9.16 (s, 1H, NH).
Embodiment 2
[0010] N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]propionamide
[0011] According to the method of Example 1, 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine was reacted with propionic anhydride for 0.5 h to obtain N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]propionamide, yield 87.2%, m.p. 159~161°C. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.13 (s, 9H, 3×CH 3 ), 1.28 (t, J = 7.6 Hz, 3H, CH 3 ), 2.54 (q, J = 7.6 Hz, 2H, CH 2 ), 8.15 (s, 1H, C 2 N 3 H 2 3-H), 8.31 (s, 1H, C 2 N 3 H 2 5-H), 9.49 (s, 1H, NH).
Embodiment 3
[0013] N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-2-butenamide
[0014] 2 mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)thiazol-2-amine dissolved in 20.0 mL dichloromethane, add 2.2 mmol 2-butenoic acid, 0.03 g 4 -Dimethylaminopyridine (DMAP), after 0.5 h, add 2.2 mmol N,N'-dicyclohexylcarbodiimide (DCC), stir at room temperature, react for 6.0 h, the reaction solution is neutralized with sodium bicarbonate aqueous solution, and stand still , Separate layers, dry the organic layer with anhydrous sodium sulfate, filter, rotary steam, and column chromatography to obtain N -[4-tert-Butyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]-2-butenamide, yield 35.8%, m.p. 205~208℃. 1 H NMR (400 MHz, CDCl 3 ) δ : 1.15 (s, 9H, 3×CH 3 ), 1.98 (dd, J = 7.0 Hz, J = 1.6 Hz, 3H, CH 3 ), 5.99 (dd, J = 14.2 Hz, J = 1.6 Hz, 1H, 3'-H), 7.13-7.19 (m, 1H, 2'-H), 8.12 (s, 1H, C 2 N 3 H 2 3-H), 8.26 (s, 1H, C 2 N 3 H 2 5-H), 8.92 (s, 1H, NH).
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