Imidazo-Pyridine Derivatives For Use In The Treatment of Herpes Viral Infection
a technology of pyridine derivatives and imidazopyridine, which is applied in the field of compounds, can solve the problems of inability to prevent infection, endanger the host's sight, and individual risk of recurrent clinical manifestations of infection, and achieve the effect of prevention or treatmen
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example 1
4-[8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine
[0333]
a) 2-Amino-3-chloropyridine
[0334]2,3-Dichloropyridine (20 g, 0.14 moles) was placed in a steel bomb. To this was added concentrated ammonium hydroxide (300 mL), the bomb sealed and heated at 190° C. for 48 hours. The vessel was cooled to room temperature and opened. Ethyl acetate and water were added. The phases were separated and the ethyl acetate phase washed with water, dried (magnesium sulfate), filtered and concentrated to a solid. This solid was crystallized from a small volume of ethyl acetate to give 12.6 g (70%) of 2-amino-3-chloropyridine as a white solid. 1H NMR (CDCl3) δ 7.95 (dd, 1H), 7.46 (dd, 1H), 6.58 (q, 1H), 5.0 (broad s, 2H); MS m / z 129 (M+H).
b) 8-Chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridine
[0335]To a solution of 3-chloro-2-pyridinamine (4.8 g, 37.4 mmol) and 2-bromo-1-(3-methoxyphenyl)ethanone (8.56 g, 37.4 mmol) in ethanol (30 mL) was added potassium carbonate (5.15 g, ...
example 2
N-Cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-8-amine
[0341]
[0342]To a solution of 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine (162 mg, 0.39 mmol) in cyclopentylamine (5 mL) was added, successively, racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (15.3 mg, 0.02 mmol), cesium carbonate (376 mg, 1.15 mmol) and palladium (II) acetate (3.5 mg, 0.015 mmol). The resulting mixture was heated in a sealed tube at 150° C. for 24 hours at which time the reaction was judged complete by thin layer chromatography. The solution was cooled to room temperature and ethyl acetate and water were added. The phases were separated and the organic layer was washed with water and brine. The combined organics were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (2:1 hexanes-ethyl acetate) to give N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxy...
example 3
4-[8-Chloro-2-(4-methylphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine
[0343]
a) 8-Chloro-2-(4-methylphenyl)imidazo[1,2-α]pyridine
[0344]In a similar manner as described in Example 1 from 2-bromo-1-(4-methylphenyl)ethanone (3.5 g, 16.4 mmol) and 3-chloro-2-pyridinamine (2.1 g, 16.4 mmol) was formed 8-chloro-2-(4-methylphenyl)imidazo[1,2-α]pyridine (4 g, 99%) as a white solid. 1H NMR (CDCl3): δ 8.06 (d, 1H), 7.90 (d, 2H), 7.89 (s, 1H), 7.26 (d, 2H), 7.24 (d, 1H), 6.72 (t, 1H), 2.40 (s, 3H); MS m / z 243 (M+1).
b) 8-Chloro-2-(4-methylphenyl)imidazo[1,2-α]pyridine-3-carbaldehyde
[0345]In a similar manner as described in Example 1 from 8-chloro-2-(4-methylphenyl)imidazo[1,2-α]pyridine (4 g, 16.4 mmol) and phosphorous oxychloride (2.29 mL, 24.6 mmol) in N,N-dimethylformamide (50 mL) was formed 8-chloro-2-(4-methylphenyl)imidazo[1,2-α]pyridine-3-carbaldehyde (1.7 g, 38%) as a white solid. 1H NMR (CDCl3): δ 10.09 (s, 1H), 9.61 (d, 1H), 7.77 (d, 2H), 7.64 (d, 1H), 7.35 (d, 2H), 7.06 (...
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