Method for preparing 4-(3-(4-hydroxylphenyl)-1,2,4-oxadiazole-5-yl)-aniline
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A technology of hydroxyphenyl and oxadiazole, which is applied in the field of chemical synthesis, can solve problems such as unseen synthetic methods, and achieve the effect of easy operation and mild conditions
Inactive Publication Date: 2011-06-08
AFFILIATED HUSN HOSPITAL OF FUDAN UNIV
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Another study disclosed the structure of a diphenyl substituted oxadiazole (DPOD) derivative, and found that it has a high affinity with β-AP (Masahiro Ono et al, Development of novel β-amyloid probes based on 3 , 5-diphenyl-1, 2, 4-oxadiazole.Bioorganic & Medicinal Chemistry, 2008, 16, 6867-6872), but there is no report on the synthesis method
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Embodiment 1
[0023] Synthesis of p-methoxybenzamide oxime
[0024] In a 100ml single-necked flask equipped with a reflux condenser, add (3.3mmol, 0.44g) benzonitrile, (3.3mmol, 0.46g) anhydrous K2 CO 3 , (3.3mol, 0.23g) the mixed solvent of hydroxylamine hydrochloride and 50ml 95% ethanol and 15ml water, reflux reaction 12h, detect reaction complete with thin-layer chromatography, stop reaction, cooling, decompression distills off part ethanol, cooling separates out solid, After filtering and drying, a white solid 1 (0.466g, 2.8mmol) was obtained with a yield of 85%.
Embodiment 2
[0026] Synthesis of 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1,2,4,-oxadiazole
[0027] Under ice-cooling, the mixture of 5mmol p-nitrobenzoyl chloride and 20ml dry toluene was added dropwise to (5mmol, 0.83g) compound 1 in 50ml toluene solution, and the drop was completed in 25min. After dropping, the temperature was raised to reflux for 10 h, and the reaction was detected by thin-layer chromatography. The reaction was stopped, the solid was precipitated by cooling, filtered, and dried to obtain a light yellow solid 2 (1.11 g, 3.75 mmol), with a yield of 75%.
Embodiment 3
[0029] Synthesis of 4-(3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)aniline
[0030] Compound 2 (0.89g, 3mmol) and stannous chloride dihydrate (3.84g, 15mmol) were dissolved in 100ml of ethanol, stirred and refluxed for 4 hours, cooled to room temperature, 300ml of 1M NaOH was added until it was alkaline, 100ml×3 acetic acid Extracted with ethyl ester, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain compound 3 (0.63 g, 2.37 mmol), with a yield of 79%.
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Abstract
The invention belongs to the field of chemical synthesis and relates to a preparation technology of a PET (Polyester Terephthalate) imaging agent, in particular to a synthesis method for a diphenyl-substituted oxadiazole derivative of a labeled precursor of a positron medicament Abeta plaque agent, i.e. 4-(3-(4-hydroxyphenyl)-1,2,4-oxadiazole-5-yl)-aniline and a reference substance of 4-(3-(4-hydroxyphenyl)-1,2,4-oxadiazole-5-yl)-N-methylaniline thereof. In the invention, the method comprises the following steps of: condensing cyanobenzene and hydroxylamine hydrochloride as raw materials to obtain p-methoxybenzamidoxime; cyclizing the p-methoxybenzamidoxime and paranitrobenzoyl chloride to obtain 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1,2,4-oxadiazole; reducing the 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1,2,4-oxadiazole and removing hydroxymethoxyl to obtain the labeled precursor; and methylating a reduzate of amine and then removing hydroxymethoxyl to obtain the reference substance. By adopting the method, the yield of obtaining the labeled precursor of a target product reaches 20%, and the whole reaction process has mild condition and is easy to operate.
Description
technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a PET imaging agent preparation technology, in particular to a positron drug β-amyloid protein (β-AP) plaque imaging agent diphenyl substituted oxadiazole (DPOD) The preparation method of the derivative, that is, the synthesis method of 4-(3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)-aniline. Background technique [0002] Positron emission tomography (PET) can be used for brain imaging with high sensitivity and good resolution. Senile dementia (Alzheimer disease, AD) is a kind of brain disease with primary mental retardation as the main manifestation, and is characterized by the degeneration of cortical cells, senile plaques and neurofibrillary tangles. The etiology of AD is still unclear, and clinical treatment is difficult. At present, the gold standard for the pathological diagnosis of AD is the appearance of senile plaques mainly composed of β-amyloid protein (β-AP) and hyperph...
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