C13 deuterated methyl telmisartan and preparation method and application thereof
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A technology of telmisartan and methyl substitution, which is applied in the field of carbon 13 deuterated methyl telmisartan and its preparation, and achieves the effects of high yield, reduced production cost, and reduced death
Inactive Publication Date: 2018-06-29
QINZHOU UNIV
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[0008] At present, there is no literature report on the synthesis of carbon-13 deuterium instead of misartan
Method used
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[0038]A kind of carbon 13 deuterium replaces the preparation method of misartan, it comprises the following steps:
[0039] 1): Mix carbon-13 deuterated methanol and iodine, and catalyze carbon-13 deuterated methyl iodide by refluxing red phosphorus (Ⅱ)
[0040]
[0041] 2): Dissolving compound (Ⅲ) in a solvent, adding base, and adding carbon 13 deuterated methyl iodide to react to obtain compound (Ⅳ)
[0042]
[0043] 3): Dissolving compound (Ⅳ) in a solvent, adding reaction base and catalyst, and preparing compound (Ⅴ) through Suzuki coupling reaction
[0044]
[0045] 4): Dissolving compound (Ⅴ) in a solvent, adding a reaction base, and obtaining carbon-13 deuterium instead of misartan through hydrolysis reaction
[0046]
[0047] As a preferred version, the above-mentioned deuterium replaces misartan-C 13 d 3 The preparation method, in the reaction described in step 1, the reaction mass ratio of carbon-13 deuterated methanol to iodine and red phosphorus is 1...
Embodiment 1
[0054] Step 1, the preparation of compound (II):
[0055]
[0056] Mix iodine element (19.5g) with carbon-13 deuterated methanol (5.0g) and place it in a 150mL constant pressure dropping funnel. , first drop a small amount of deuterated methanol mixture that dissolves part of the iodine in the constant pressure dropping funnel into the round bottom flask, then heat to reflux, and when the temperature rises to about 50°C, drop the remaining mixed solution into the round bottom flask in batches in the flask. The dropwise addition was completed in about 30 minutes. The reflux continued to dissolve the iodine and drop it in. After all the iodine in the dropping funnel was dissolved, stop heating and cool to room temperature. After stirring at room temperature for 1 h, distill at atmospheric pressure, collect fractions at 41 to 44 ° C, and use saturated Na 2 S 2 o 3 Wash 3 times, wash 2 times with saturated brine, add anhydrous CaCl 2 After drying, 13.8 g of carbon-13 deut...
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Abstract
The invention belongs to the field of organic medicinal synthesis, and discloses C13 deuterated methyl telmisartan and a preparation method and application thereof. According to the preparation method, with C13 deuterated methanol as a C13 deuterated raw material, the C13 deuterated telmisartan is synthesized through a four-step reaction. The preparation method comprises the following steps: iodizing the C13 deuterated methanol to obtain C13 deuterated iodomethane; performing a substitution reaction on the C13 deuterated iodomethane and a compound (III) to obtain a compound (IV); performing aSuzuki coupling reaction on the compound (IV) and 2-boro methylbenzoate to obtain a compound (V); performing esterolysis on the compound (V) under an alkaline condition to obtain the C13 deuterated telmisartan. The preparation method is easy and convenient to operate; by the preparation method, a C13 deuterated reagent is saved, the cost is low and purification is easy; a purified product is obtained after rapid preparation and chromatographic purification. A standard deuterated telmisartan substance prepared by the preparation method provided by the invention is high in purity and stable in chemical properties, and can be applied to preparation of an analytical standard substance.
Description
technical field [0001] The invention relates to the technical field of medicine, in particular to the technical field of organic drug synthesis, in particular to a carbon-13 deuterated methyl telmisartan and a preparation method and application thereof. Background technique [0002] Telmisartan, as an angiotensin (AT1) II receptor antagonist, is a new type of antihypertensive drug. The compound was developed by Boehringer Ingethiem in Germany, and it was first launched in the United States in March 1999, and in Germany in the same year. Non-peptide angiotensin II receptor antagonists can selectively and irreversibly block ATI receptors without affecting other receptor systems. For mild to moderate high blood pressure. Telmisartan is a new type of antihypertensive drug and a specific angiotensin II receptor (ATI type) antagonist for the treatment of essential hypertension. The alternative angiotensin II receptor binds with high affinity to the ATI receptor subtype (the kno...
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