Containing 2-anilino-4-thiazolyl pyridine derivative and its preparation method, pharmaceutical composition and application
A technology of methylthiazole and pyridine, applied in the field of treating tumor diseases
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Embodiment 1
[0214] Example 1.2-(m-trifluoromethylanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine
[0215]
[0216] 2-Bromo-4-(2-amino-4-methylthiazol-5-yl)pyridine (270mg, 1mmol) was added to 10ml of mixed solvent (1N HCl / H 2 O / Dioxane=2 / 4 / 1), heated to 80°C with stirring, added m-trifluoromethylaniline (242mg, 1.5mmol) after dissolution, raised the temperature, and refluxed until the reaction was complete. Cool to room temperature, pour the reaction solution into saturated aqueous sodium bicarbonate solution, filter, collect the solid, and purify by column chromatography to obtain the product 2-(m-trifluoromethylanilino)-4-(2-amino-4-methyl thiazol-5-yl)pyridine. 1 H-NMR(400MHz,DMSO-d6):δ(ppm):9.43(s,1H,-N H -),9.23(s,1H,Ar H ),8.14(d,1H,Ar H ),7.86(d,1H,Ar H ),7.47(t,1H,Ar H ),7.26(s,2H,-N H 2 ),7.18(d,1H,Ar H ),6.81(s,1H,Ar H ),6.77(d,1H,Ar H ),2.32(s,3H,-C H 3 ); m / z351.0[M+H] + .
Embodiment 2
[0217] Example 2.2-(2-chloro-6-methylanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine
[0218]
[0219] Replace m-trifluoromethylaniline with 2-chloro-6-methylaniline, and refer to the operation process of Example 1 to obtain 2-(2-chloro-6-methylanilino)-4-(2-amino-4 -Methylthiazol-5-yl)pyridine. 1 H-NMR(300MHz,DMSO-d6):δ(ppm):8.30(s,1H,-N H -),7.89(d,1H,Ar H ),7.36-7.34(d,1H,Ar H ),7.26-7.24(d,1H,Ar H ),7.19-7.14(m,3H,Ar H ,-N H 2 ),6.60-6.58(dd,1H,Ar H ),6.37(s,1H,Ar H ),2.23(s,3H,-C H 3 ),2.18(s,3H,-C H 3 ); m / z331.0[M+H] + .
Embodiment 3
[0220] Example 3.2-(2-fluoroanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine
[0221]
[0222] Replace m-trifluoromethylaniline with 2-fluoroaniline, and refer to the operation process of Example 1 to obtain 2-(2-fluoroanilino)-4-(2-amino-4-methylthiazol-5-yl)pyridine . 1 H-NMR(300MHz,DMSO-d6):δ(ppm):8.71(s,1H,-N H -),8.26-8.20(m,1H,Ar H ),8.05(d,1H,Ar H ),7.22-7.09(m,4H,-N H 2 , Ar H ),6.99-6.93(m,2H,Ar H ),6.73-6.70(m,1H,Ar H ),2.30(s,3H,-C H 3 ); m / z301.0[M+H] + .
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