Preparation method of micromolecule cathepsin D inhibitor
A technology of small molecules and inhibitors, which is applied in the field of preparation of small molecule cathepsin D inhibitors, can solve the problems of long reaction time, low yield, pollution and the like, and achieves the effects of simple operation, simple reaction conditions and simple post-treatment.
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Embodiment 1
[0021] (I) Preparation of 4-(2-benzothiazylthio)aniline
[0022] First add 2-mercaptobenzothiazole (1.67g, 10mmol), p-aminoiodobenzene (2.63g, 12mmol), catalyst CuI (0.19g, 1mmol), Na 2 CO 3 (1.06g, 10mmol) and H 2 O (20mL), heated to 120°C and refluxed for 24h, the reaction was completed, cooled to room temperature, the reaction liquid was extracted with ethyl acetate, the obtained organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and spin-dried, PE:EA= 2.09 g of 4-(2-benzothiazylsulfanyl)aniline was obtained by passing through the column at 6:1, with a yield of 86.0%.
[0023] (Π) Preparation of a small molecule cathepsin D inhibitor
[0024] Dissolve 4-(2-benzothiazylthio)aniline (1.29g, 5mmol) and 3,5-dichloro-2-hydroxybenzoic acid (1.04g, 5mmol) in CH 2 CL 2 (20mL), add the acylating agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.96g, 5mmol), heat to 40°C under reflux for 8h, After the reaction is complet...
Embodiment 2
[0026] (I) Preparation of 4-(2-(6-chlorobenzothiazylthio))aniline
[0027] First add 2-mercapto-6-chlorobenzothiazole (2.02g, 10mmol), p-aminoiodobenzene (2.63g, 12mmol), catalyst CuI (0.19g, 1mmol), Na 2 CO 3 (1.06g, 10mmol) and H 2 O (20mL), heated to 120°C and refluxed for 24h, the reaction was completed, cooled to room temperature, the reaction liquid was extracted with ethyl acetate, the obtained organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and spin-dried, PE:EA= 2.46 g of 4-(2-(6-chlorobenzothiazylsulfanyl))aniline was obtained in a 6:1 column with a yield of 84.0%.
[0028] (Π) Preparation of a small molecule cathepsin D inhibitor
[0029] Dissolve 4-(2-(6-chlorobenzothiazylthio))aniline (1.46g, 5mmol) and 3,5-dichloro-2-hydroxybenzoic acid (1.04g, 5mmol) in CH 2 CL 2 (20mL), add the acylating agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.96g, 5mmol), heat to 40°C under reflux for 8h, After the re...
Embodiment 3
[0031] (I) Preparation of 4-(2-(6-methoxybenzothiazylthio))aniline
[0032] First add 2-mercapto-6-methoxybenzothiazole (1.97g, 10mmol), p-aminoiodobenzene (2.63g, 12mmol), catalyst CuI (0.19g, 1mmol), Na 2 CO 3 (1.06g, 10mmol) and H 2 O (20mL), heated to 120°C and refluxed for 24h, the reaction was completed, cooled to room temperature, the reaction liquid was extracted with ethyl acetate, the obtained organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and spin-dried, PE:EA= 2.39 g of 4-(2-(6-methoxybenzothiazylsulfanyl))aniline was obtained by 6:1 column, with a yield of 83.2%.
[0033] (Π) Preparation of a small molecule cathepsin D inhibitor
[0034] 4-(2-(6-methoxybenzothiazylthio))aniline (1.44g, 5mmol) obtained in step 1 was dissolved in 3,5-dichloro-2-hydroxybenzoic acid (1.04g, 5mmol) in CH 2 CL 2 (20mL), add the acylating agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.96g, 5mmol), heat to 40°C under r...
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