Aldh-2 inhibitors in treatment of addiction
An R20, compound technology, applied in the field of new ALDH-2 inhibitors, can solve the problem of no proof and so on
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[0348] Preparation of the compound of step 1-chemical formula (2)
[0349] Usually, make the compound of chemical formula I (wherein R 1 is benzonitrile), dibutyltin oxide, and azidotrimethylsilane were subjected to microwaves. The reaction is carried out at a temperature of about 150°C for about 10-30 minutes. When the reaction is substantially complete, the product of formula (2) is isolated by conventional means, for example by chromatography on silica gel.
[0350] Step 2 - Preparation of Compounds of Formula I
[0351] The purified product of formula (2) is suspended in an aqueous solvent such as acetonitrile / water and a catalytic amount of a strong acid such as trifluoroacetic acid is added. The solvent is removed to provide a compound of formula I, wherein R 1 is phenyl substituted by tetrazol-5-yl.
[0352] Similarly, where R 1 Is the compound of formula I of [1,2,4]-oxadiazol-3-yl substituted by benzonitrile at the 5-position into wherein R 1 is a compound ...
Embodiment 1
[0466] Preparation of compounds of formula R1WX
[0467] A. Preparation of compounds of formula (4), wherein R is phenyl
[0468]
[0469] A 50 mL round bottom flask equipped with a condenser was charged with benzamide (compound of formula (b), 363.4 mg, 3.0 mmol) and 1.3-dichloroacetone (457.1 mg, 3.6 mmol, 1.2 equiv). The mixture was heated at 130° C. for 1 hour under nitrogen atmosphere. After cooling to room temperature, the resulting mixture was purified by recrystallization from acetonitrile (6 mL). The suspension was heated under reflux reaction conditions for 5 minutes and then cooled to ambient temperature. The resulting solid was filtered through a glass filter, and the crystals on the filter were washed with acetonitrile (2 mL). The desired product, 4-(chloromethyl)-2-phenyl-1,3-oxazole, was obtained as a colorless powder.
[0470] b. Preparation of other compounds of formula (4a), wherein R is phenyl
[0471] Similarly, following the procedure of Exam...
Embodiment 2
[0501] The preparation of the compound of chemical formula (5)
[0502]
[0503] step 1- The preparation of the compound of chemical formula (9)
[0504] 1-(2-Hydroxy-4-methoxyphenyl)ethan-1-one (20 g, 120 mmol) and N,N-dimethylformamide dimethyl acetal (23 g, 181 mmol) were stirred at 90°C mixture for 2 hours. After cooling to room temperature, the reaction mixture afforded a yellow precipitate which was washed with ethyl acetate (3 x 30ml), water (2 x 50ml) and then dried under reduced pressure to give 3-(Dimethylamino)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (9); MS 222.1 (M+H).
[0505] Step 2- The preparation of the compound of chemical formula (5)
[0506] 3-(Dimethylamino)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (20.0 g, 90.37 mmol) was dissolved in anhydrous chloroform ( To a solution in 100 ml) was added N-iodosuccinimide (23.5 g, 99.22 mmol) and silica gel (40 g). The reaction mixture was stirred at 0°C for 60 minutes, then the insoluble mater...
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