Tag: M.W=100-200

1195768-18-3, A common heterocyclic compound, 1195768-18-3, name is Methyl 3-amino-2-fluorobenzoate, molecular formula is C8H8FNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To the reaction flask were added methyl 2-fluoro-3-aminobenzoate (20 g, 118.23 mmol), bromomethylcyclopropane (20.75 g, 153.70 mmol), N,N-dimethylformamide (200 mL) , stirred under reflux for 16 h, monitored by TLC to reactionWhen not in progress, turn off the heat and end the reaction. After the reaction mixture was cooled to room temperature, water (200 mL) was added, and the mixture was evaporated.Purification by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1) afforded pale-yellow liquid product 2-fluoro-(3-(cyclopropylmethyl)amino)benzoic acid methyl ester (13 g, yield 49.39%).

The synthetic route of 1195768-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Taihe International Trade Co., Ltd.; Lv Liang; Liu Jiyong; Xiang Juncheng; Ma Wenjing; Zhou Liqi; Hou Shuang; Ni Jueping; Li Zongcheng; (56 pag.)CN108586279; (2018); A;,
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A common compound: 4341-76-8, name is Ethyl 2-butynoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4341-76-8

General procedure: In a two neck rbf was stirred a mixture of Pd(OAc)2 (275 mg,1.22 mmol) and TDMPP (540 mg, 1.22 mmol) in benzene (30 ml)for 15 min at rt under nitrogen. To this mixture was added ethyl-2-butynoate 7 (2.84 ml, 24.48 mmol) and the resulting mixturewas further stirred for 10 min at rt. Next, ethynylbenzene 4a(2.50 g, 24.48 mmol) was added to this solution and the mixturewas stirred for 5-10 min until reaction was completed. Theworkup of reaction was performed by evaporating the solvent invacuum followed by column chromatography (Hexane:EtOAc = 100:1) to give the desired compound 8a (2.62 g);

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4341-76-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singh, Sarbjit; Goo, Ja-Il; Noh, Hyojin; Lee, Sung Jae; Kim, Myoung Woo; Park, Hyejun; Jalani, Hitesh B.; Lee, Kyeong; Kim, Chunsook; Kim, Won-Ki; Ju, Chung; Choi, Yongseok; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1394 – 1405;,
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344-14-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below.

(8R, 8S)-3-Fluoro-2-hydroxy-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H- pyrimido[1 ,2-a]pyrimidin-4-one can be prepared in the following way. 5.6 g of sodium methoxide are added to a suspension of 7 g of (4R,4S)-4-(trifluoromethyl)-1 ,4,5,6-tetrahydropyrimidin-2-ylamine hydrochloride in 35 ml of dimethyl fluoropropanedioate. After stirring the suspension for 3 hours at a temperature of 100C, the medium obtained is concentrated to dryness under reduced pressure. The residue is taken up in diethyl ether and then dried with suction under vacuum. The solid obtained is taken up in 14 ml of water, and the resulting mixture is cooled in ice, before acidification to pH 5-6 by addition of concentrated hydrochloric acid (25%). After 2 hours of stirring at a temperature of 0C and then overnight at a temperature of about 20C, the suspension is filtered and then the solid is dried with suction and dried under vacuum over P2O5. 6.5 g of (8R, 8S)-3- fluoro-2-hydroxy-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1 ,2- a]pyrimidin-4-one are obtained in the form of a yellow powder, the characteristics of which are the following: Mass spectrum (method A) (ES +/-) [M+H]+: m/z 254; [M-H]-: m/z 252; Tr (min) = 0.28

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SANOFI; EL-AHMAD, Youssef; FILOCHE-ROMME, Bruno; LETALLEC, Jean-Philippe; MARCINIAK, Gilbert; RONAN, Baptiste; VIVET, Bertrand; WO2013/190510; (2013); A2;,
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344-14-9, Name is Dimethyl 2-fluoromalonate, 344-14-9, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2¡Á20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

Statistics shows that Dimethyl 2-fluoromalonate is playing an increasingly important role. we look forward to future research findings about 344-14-9.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
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2318-25-4, Adding a certain compound to certain chemical reactions, such as: 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2318-25-4.

To 3-amino-2-chloro-pyridine 1k1 (964 mg, 7.5 mmol, 1 eq) was added imidate 1g2 (1.47 g, 7.5 mmol, 1 eq) in ethanol (15 mL) under a N2 atmosphere. The mixture was stirred at RT for 24 h at which point the reaction was concentrated and purified directly on a silica gel column (eluent: EtOAc/Hexanes (1:9)) to afford adduct 1k2 (1.54 g, 76percent) as a clear oil

According to the analysis of related databases, 2318-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/19905; (2006); A1;,
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89-91-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89-91-8 as follows.

j00471j A mixture of(4-chloro-3-fluorophenyl)methanamine (2.0 g, 12.5 mmol) and methyl 2,2- dimethoxyacetate (3.4 g, 25.1 mmol) was stirred at 140 C for 1 hour in microwave. On completion, the reaction was diluted with dichloromethane (200 mL) and concentrated under reduced pressure togive compound B-100 (4.9 g, crude) as a yellow gum. LCMS (B): tR = 0.665 mm., (ES) mlz (M+H)=262.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 89-91-8, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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A common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 105-53-3.

A solution of Malonate 2.2 (1 eq) and acid (trifluoroacetic acid) (0.1 eq.) was prepared in acetonitrile (5 volumes) and was added slowly at a rate such that the internal temperature never exceeded 25 C. (time of addition=10-15 minutes). The reaction was complete in two hours at room temperature and achieve an in-solution conversion of 76%

The synthetic route of Diethyl malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OptMed, Inc.; Gondi, Vijaya Bhasker; Reid, John Gregory; US2013/197263; (2013); A1;,
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4385-35-7, These common heterocyclic compound, 4385-35-7, name is 3-Isochromanone, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A. o-[(carboxymethyl)benzyl]triphenylphosphonium bromide. 3-Isochromanone (30 g), Mann, F. G. and Stewart, F. H., Journal of the Chemical Society 2819 (1954) is added with swirling to 150 ml of hydrobromic acid (48%) at 80 C. The resulting mixture is then heated on a steam bath with occasional swirling for 10 min and thereafter poured into a mixture of crushed ice and water (750 g). The resulting mixture is then extracted with ethyl acetate and the ethyl acetate extracts washed with a mixture of water and brine (1:1) and dried over magnesium sulfate. Concentration under reduced pressure yields a residue of crude o-(bromomethyl)phenylacetic acid. (Crystallization of the crude product from methylene chloride yields a product with melting point 130-131 C. and a C:H ratio of 46.90:4.09).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4385-35-7.

Reference:
Patent; The Upjohn Company; US4281113; (1981); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1559-02-0

Example 91 2″-amino-6′-(5-chloropyrid-3-yl)-l”-methyldispiro[cyclopropane-l,3′-chroman-4′,4″- imidazol]-5′(l’H)-oneStep A: A mixture of diethyl cyclopropane-l,l-dicarboxylate (14.1 mL, 80.6 mmol) and lithium tri-tert- butoxyaluminohydride (201.4 mL, 201.4 mmol) was heated to reflux in THF for 3 hours. The mixture was cooled down and partitioned between water and EtOAc. The organics were washed with water, brine and dried with Na2S04. This was concentrated down and then purified on a column using 10 to 50% EtOAc:hexanes to give ethyl l-(hydroxymethyl)cyclopropanecarboxylate (1.5 g, 10.4 mmol, 12.9%) as an 12.9%) as an oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1559-02-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 23786-14-3 as follows. 23786-14-3

Methyl bromo(4-methoxyphenyl)acetate; A mixture of 13.4 g (74.4 mmol) of methyl (4-methoxyphenyl)acetate, 13.9 g (78.1 mmol) of Lambda/-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (120 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered and the solvent was removed in vacuo. Yield: 18.98 g (98%) of yellow oil1H-NMR (CDCI3): 3.78 (s, 3H), 3.81 (s, 3H), 5.35 (s, 1 H), 6.88 (d, 8.7 Hz, 2H), 7.48(d. 8.7 Hz, 2H).MS (API-ES,pos) m/z = 179 [M+H-Br]+

According to the analysis of related databases, 23786-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics