Triazole derivative and use thereof
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preparation example 1
[0086]1-1. Preparation of the Compound of Formula 1 Based on Chemical Equation 1
[0087]Compounds 1 to 14 belonging to Formula 1 of the present disclosure can be prepared according to the following Chemical Equation 1:
[0088]Compound c can be obtained by Click reaction from Compound a and Compound b prepared through commonly known methods. More specifically, it can be obtained by adding a catalytic amount of Cu ion and a reducing agent (for example, sodium ascorbate) under a certain ratio of water and quaternary butyl alcohol solvent conditions, and performing the reaction for 8 to 24 hours at room temperature. An aqueous acid solution such as hydrochloric acid is added to the obtained triazole Compound c under methanol solvent conditions, and the protecting groups are deprotected at room temperature or 50° C. to obtain the final products Compounds 1 to 14.
[0089]1-2. Preparation of Compound 3 Based on Chemical Equation 1
[0090]4-fluorophenyl azide (a-3) (100 mg, 0.73 mmol) and 4-ethynyl...
preparation example 2
[0135]2-1. Preparation of the Compound of Formula 1 Based on Chemical Equation 2
[0136]Compounds 15 to 17 belonging to Formula 1 of the present disclosure can be prepared according to the following Chemical Equation 2:
[0137]After performing the reaction of adding various alkylamines including epoxide, alkylamine, alcohol functional groups to Compound 4 obtained through Chemical Equation 1, an aqueous acid solution such as hydrochloric acid is added under methanol solvent conditions, and the protecting groups are deprotected at room temperature or 50° C. to obtain the final products Compounds 15 to 17.
[0138]2-2. Preparation of Compound 16 Based on Chemical Equation 2
[0139]After dissolving Compound 4 (100 mg, 0.28 mmol) in dimethylformamide (2 ml), potassium carbonate (154 mg, 1.12 mmol) and 2-chloro-N,N-dimethoxyethane-1-amine (80 mg, 0.56 mmol) were added, followed by heating and stirring at 110° C. for 5 hours. After checking the completion of the reaction, it was cooled at room tem...
preparation example 3
[0150]3-1. Preparation of the Compound of Formula 1 Based on Chemical Equation 3
[0151]Compounds 18 to 19 belonging to Formula 1 of the present disclosure can be prepared according to the following Chemical Equation 3:
[0152]Compound j can be obtained by Click reaction from Compound h and Compound i prepared through commonly known methods. More specifically, it can be obtained by adding a catalytic amount of Cu ion and a reducing agent (for example, sodium ascorbate) under a certain ratio of water and quaternary butyl alcohol solvent conditions, and performing the reaction for 8 to 24 hours at room temperature. Compound k or Compound 1 can be obtained by reacting the ester functional group of Compound j with various alkylamines including a dialkylamine group at high temperature.
[0153]And then, the final products Compounds 18 to 19 can be obtained through a deprotection process.
[0154]3-2. Preparation of Compound 18 Based on Chemical Equation 3
[0155]Methyl 4-azidobenzoate (h) (200 mg, 1...
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