- PROCESS FOR THE PREPARATION OF VERDIPERSTAT
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An improved process for preparing verdiperstat is disclosed. The process includes the steps of reacting a compound having formula or a salt thereof, wherein R is the same or different and is each independently a C1-C5 alkyl with 3-(dimethylamino)acrylonitrile to obtain a compound having formula; and converting the compound having formula to verdiperstat.
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Paragraph 0043-0044
(2021/11/13)
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- Preparation method of 2-chloro-5-cyanopyrimidine compound
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The invention discloses a preparation method of a 2-chloro-5-cyanopyrimidine compound. A route adopted by the preparation method is as follows: cyanoacetic acid is used as a raw material, ioxane is used as a solvent, and a reaction is conducted under the action of N,N-dimethylformamide dimethyl acetal so as to generate 3-(dimethylamino)acrylonitrile, and then a Vilsmeier reaction, an addition reaction, a ring closing reaction and a chlorination reaction are sequentially carried out to finally obtain a finished product, i.e., the 2-chloro-5-cyanopyrimidine compound. According to the synthetic route provided by the preparation method, raw materials are cheap and easily available; aftertreatment is simple; purification is easy; column chromatographic purification is not needed in each step ofreaction; the method can effectively overcome the technical defects of long route, expensive raw material cost, need of column chromatography and the like of other synthesis methods in the prior art;and the preparation method of the 2-chloro-5-cyanopyrimidine compound provided by the invention has important economic benefits on reduction of the drug cost, and is a technology which is low in costand suitable for industrial production.
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Paragraph 0028; 0032
(2020/03/09)
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- A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions
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Herein, we report a new prebiotically plausible pathway towards a pyrimidine nucleobase in continuous manner. The route involves simultaneous methylation and carbamoylation of cyanoacetylene-derived α,β-unsaturated thioamide with N-methyl-N-nitrosourea (MNU) in aqueous media. This provides S-methylpyrimidinone in one-pot, which can be converted into a variety of 4-substituted pyrimidine nucleobases including cytosine and uracil.
- Okamura, Hidenori,Becker, Sidney,Tiede, Niklas,Wiedemann, Stefan,Feldmann, Jonas,Carell, Thomas
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supporting information
p. 1939 - 1942
(2019/05/02)
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- Hydrogenolysis of Amide Acetals and Iminium Esters
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Amide acetals and iminium esters were hydrogenated into amines under very mild reaction conditions over common hydrogenation catalysts. This finding provides a new strategy for the selective reduction of amides. The synthetic utility of this approach was demonstrated by the selective reduction of amides bearing ester and nitrile groups.
- Kadyrov, Renat
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p. 170 - 172
(2017/12/26)
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- A process for preparing N, N - dimethyl - 1, 3 - propanediamines method
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The invention relates to a method for preparing N,N-dimethyl-1,3-diaminopropane. The method comprises the steps that acrylonitrile is added into a synthesis kettle, and dimethylamine is added and then removed through decompressing rectifying to prepare N,N-dimethyl amine acrylonitrile; a hydrogenation catalyst is added, liquid ammonia is introduced into the high-pressure kettle, hydrogen is introduced, reacting is performed, settling is performed, then prefractionation is performed, and rectifying is performed to obtain the N,N-dimethyl-1,3-diaminopropane. According to the method for preparing the DMAPA, the technology is simple, improvement of the selectivity is guaranteed, the yield per unit of double slag is greatly decreased, and a large amount of dangerous waste treatment charge is saved; consumption of the raw materials of the acrylonitrile and the dimethylamine is reduced, the raw material consumption cost of a DMAPA synthesis device is saved, that is, the production cost is saved, and the enterprise benefits are increased.
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Paragraph 0036; 0043; 0051
(2017/08/26)
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- Synthesis method of 3-amino-5-N,N-dimethyl pyrazole
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The invention relates to a synthesis method of 3-amino-5-N,N-dimethyl pyrazole, and belongs to the field of chemical synthesis. Aiming at problems that when amino-containing pyrazole compounds are prepared by a conventional one-pot method, the yield and the activity of the compounds are low, and the synthesized products are liable to decompose when affected by the environment, the synthesis method comprises the steps of preparing N-methoxymethylene-N,N-dimethylmethanesulfonamide from methyl iodide and dimethylformamide, preparing sodium cyanoacetate from cyanoacetic acid and sodium hydroxide, and then preparing N,N-dimethylaminoacrylonitrile by mixing N-methoxymethylene-N,N-dimethylmethanesulfonamide and sodium cyanoacetate, and then by conducting a reaction between N,N-dimethylaminoacrylonitrile and hydrazine hydrate, 3-amino-5-N,N-dimethyl pyrazole is obtained. By adopting a two-step method for preparing 3-amino-5-N,N-dimethylpyrazole, the yield of the N, N-dimethyl pyrazole compound is increased to 75-80%.
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Paragraph 0008; 0009; 0010
(2017/08/28)
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- A 3-difluoromethyl-1-methyl -1H-pyrazole-4-carboxylic acid
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The invention relates to a preparation method of 3-difluoromethyl-1-methyl-1H-pyrazolyl-4-carboxylic acid, which comprises the following steps: reacting sodium cyanoacetate and imide salt to obtain N,N-dimethylaminoacrylonitrile, and reacting with difluoroacetyl chloride to obtain 2-((dimethylamino)methylene)-4,4-difluoro-3-carbonylbutyronitrile; reacting with methyl hydrazine to obtain 1-methyl-3-difluoromethyl-4-pyrazolylnitrile; and finally, reacting the 1-methyl-3-difluoromethyl-4-pyrazolylnitrile with sodium hydroxide to obtain the 3-difluoromethyl-1-methyl-1H-pyrazolyl-4-carboxylic acid. The method has the advantages of simple and accessible raw materials, low price, short process route, mild reaction conditions, low facility requests, high total reaction yield (more than 52%) and high product purity (more than 99.2%). The method has the characteristics of simple and reasonable technique, mild reaction conditions, high yield and low cost, can easily implement industrialization, and has wide application prospects.
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Paragraph 0030; 0031; 0034; 0043; 0044
(2018/01/19)
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- Catalytic Hydrogenation for the Preparation of Amines from Amide Acetals, Ketene N,O-Acetals or Ester Imides
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The present invention relates to a process for the preparation of amines, comprising the following steps: Reaction of a (i) amide acetal of the general formula (I), or (ii) ketene N,O-acetal of the general formula (II), or (iii) ester imide of the general formula (III) with H2 in the presence of a hydrogenation catalyst, where catalyst and amide acetal or ketene N,O-acetal or ester imide are used in a molar ratio of from 1:10 to 1:100 000 and where a hydrogen pressure of from 0.1 bar to 200 bar is established and where a temperature in the range of from 0° C. to 250° C. is established.
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Paragraph 0155; 0156
(2016/10/04)
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- Esterification of carboxylic acids and etherification of phenols with amide acetals
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The esterification and etherification of unhindered, as well as severely hindered, carboxylic acids and phenols with basic amide acetals, such as N,N-dimethylformamide dimethyl acetal, and their side reactions are discussed. Modified procedures are descri
- Vorbrüggen, Helmut
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experimental part
p. 1603 - 1617
(2009/04/07)
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- Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors
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A structure-activity relationship study of dorsomorphin, a previously identified inhibitor of SMAD 1/5/8 phosphorylation by bone morphogenetic protein (BMP) type 1 receptors ALK2, 3, and 6, revealed that increased inhibitory activity could be accomplished by replacing the pendent 4-pyridine ring with 4-quinoline. The activity contributions of various nitrogen atoms in the core pyrazolo[1,5-a]pyrimidine ring were also examined by preparing and evaluating pyrrolo[1,2-a]pyrimidine and pyrazolo[1,5-a]pyridine derivatives. In addition, increased mouse liver microsome stability was achieved by replacing the ether substituent on the pendent phenyl ring with piperazine. Finally, an optimized compound 13 (LDN-193189 or DM-3189) demonstrated moderate pharmacokinetic characteristics (e.g., plasma t1/2 = 1.6 h) following intraperitoneal administration in mice. These studies provide useful molecular probes for examining the in vivo pharmacology of BMP signaling inhibition.
- Cuny, Gregory D.,Yu, Paul B.,Laha, Joydev K.,Xing, Xuechao,Liu, Ji-Feng,Lai, Carol S.,Deng, Donna Y.,Sachidanandan, Chetana,Bloch, Kenneth D.,Peterson, Randall T.
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supporting information; scheme or table
p. 4388 - 4392
(2009/04/06)
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- ORTHOAMIDES, XLVIII REACTIONS OF AN AZAVINYLOGUE AMINALESTER WITH CH2-ACIDIC COMPOUNDS
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Condensation reactions of azavinylogue orthoamides 5a and 6a with CH2-acidic compounds are described.Reaction products are formylated - or azavinylogue formylated compounds 8 and 9 resp.The condensation reactions of 5a can be enhanced by addition of trimethyl borate.Under these conditions the formylations reaction-leading to compounds of type 8 - is preferred.
- Kantlehner, Willi,Hauber, Michael
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p. 697 - 704
(2007/10/02)
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- Process for producing dialkyl aminoacrylonitrile
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A process for producing a dialkyl aminoacrylonitrile by treating dimethylaminopropionitrile with a hydrogen acceptor in the presence of a dehydrogenation catalyst. The dialkylaminoacrylonitrile thus produced is converted to aminomethylene malonitrile, a known intermediate for thiamine.
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