Guanidinobenzoic acid ester compound
A technology of guanidinobenzoyl and compound, which is applied in the field of guanidinobenzoate compounds, can solve the problems of high cost, low practice of low-protein diet therapy, and low compliance
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[0194] Hereinafter, the production method of the compound of formula (I) is demonstrated in more detail based on an Example. It should be noted that the present invention is not limited to the compounds described in the following examples. In addition, the production methods of the raw material compounds are shown in the production examples. In addition, the production method of the compound of formula (I) is not limited to the production method of the specific examples shown below, and the compound of formula (I) can also be produced by a combination of these production methods or by a method obvious to those skilled in the art .
[0195] In addition, the following abbreviations may be used in Examples, Production Examples, and Tables described below.
manufacture example 1
[0199] tert-butyl 4-methylthiophene-2-carboxylate (12.0g), N-bromosuccinimide (10.8g), 2,2'-azobisisobutyronitrile (496mg) and carbon tetrachloride (119 mL) was stirred at 90°C for 1 hour. Then N-bromosuccinimide (1.08 g) was added and stirred at 90°C for 1 hour. The reaction suspension was cooled to room temperature, then the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 4-(bromomethyl)thiophene-2-carboxylate (16.3 g).
[0200] To a solution of 4-(bromomethyl)thiophene-2-carboxylic acid tert-butyl ester (9.90 g) in N,N-dimethylformamide (100 mL) was added glycine tert-butyl ester hydrochloride (18.0 g) and triethyl amine (19.9 mL), and stirred at 60°C for 15 hours. The reaction suspension was cooled to room temperature, then sodium triacetoxyborohydride (22.7 g) was added, and stirred at room temperature for 5 hours. Water...
manufacture example 2
[0202] To a solution of 6-hydroxy-2-naphthoic acid (220mg) in N,N-dimethylformamide (3.30mL) was added 4-{[(2-tert-butoxy-2-oxoethyl)amino] Methyl}thiophene-2-carboxylic acid tert-butyl ester (383mg), O-(7-azobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (489 mg) and N,N-diisopropylethylamine (500 μL), and stirred at room temperature for 20 hours. Then O-(7-azobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (222 mg) and N,N-diisopropylethyl amine (200 μL) and stirred at room temperature for 6 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed successively with water and saturated aqueous sodium chloride, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 4-{[(2-tert-butoxy-2-oxoethyl)(6-hydroxy-2-naphthoyl)amino] Methyl}thiophene-2-carb...
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