Tag: M.W=200-300

Synthetic Route of 1132-95-2,Some common heterocyclic compound, 1132-95-2, name is 1,1-Diisopropoxycyclohexane, molecular formula is C12H24O2, 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.

The product from (1) was dissolved in 310 mL of acetone. 127,5 g of 1,1- diisopropoxycyclohexane and 31.0 g of pyridine hydrobromide were added. The mixture was stirred at 40-45 C for 3 hours. Then 300 mL of isopropyl acetate, 250 mL of 5% aqueous sodium carbonate and 9 mL of 20% aqueous sodium hydroxide were added. After stirring the aqueous phase was seperated off, and the organic phase was concentrated by distilling under vacuum. 246 g of a mixture 2′, 4″-0- bis (trimethylsilyl) erythromycin A 9- {O- [1- (1- methylethoxy)-cyclohexyl] oxime} and isopropyl acetate was obtained.; (2) The product obtained above in (1) was dissolved in 310 mL of acetone. 127,5 g of 1,1- diisopropoxycyclohexane and 31.0 g of pyridine hydrobromide were then added. The mixture was stirred at 40-45 C for 3 hours. Then 300 mL of isopropyl acetate, 250 mL of 5% aqueous sodium carbonate and 9 mL of 20% aqueous sodium hydroxide were added. After stirring and the aqueous phase was seperated off, and the organic phase was concentrated by distilling under vacuum. 236 g of a mixture 2′, 4″-0- bis (trimethylsilyl) erythromycin A 9- {O- [1- (1-methylethoxy)-cyclohexyl] oxime} and isopropyl acetate was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Diisopropoxycyclohexane, its application will become more common.

Reference:
Patent; SANDOZ AG; WO2005/90377; (2005); A1;,
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Related Products of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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.

Indoline (9a) (1.6 mL, 12.9 mmol) was added dropwise with stirring to triethyl methanetricarboxylate (3.2 mL, 12.9mmol) heated to 215C, at such a rate that the temperature of the reaction mixture was maintained within ¡À5C of the initial temperature. The ethanol eliminated during the reaction was distilled through a suitable still-head. After adding all the indoline the reaction mixture was maintained at the same temperature for 10-15 min, after which it was cooled. The solid ester 5a was filtered off, washed with water, and dried. Yield 1.3 g (38%); mp 303.0 -304C LC-MS (M+1) 260.4 1H NMR (300 MHz, DMSO) delta 13.10 (s, 1H), 7.68 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 7.1 Hz, 1H), 7.22 – 7.13 (m, 1H), 4.33 (q, J = 7.1 Hz, 2H), 4.26 – 4.16 (m, 2H), 3.37 (s, 1H), 3.32 (s, 1H), 1.31 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Triethyl methanetricarboxylate, its application will become more common.

Reference:
Article; Huddar, Srigouri; Jang, Soojin; Kim, Hyung Jun; Lee, Sunkyung; Park, Chul Min; Bioorganic and medicinal chemistry letters; (2020);,
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Synthetic Route of 107045-28-3,Some common heterocyclic compound, 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, molecular formula is C12H17NO2, 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 solution of 5-bromo-2-iodobenzoic acid (5. 00g, 15. [3MMOL)] in dimethylformamide [(60ML)] was treated with EDAC. [HC1] (3.. [51G, 18. 4MMOL), 1-] [HYDROXYBENZOTRIAZOLE] hydrate (2. [48G,] 18. 4mmol), and 4-aminomethylbenzoic acid tert-butyl ester (3.74g, 18. [4MMOL),] then stirred overnight at room temperature. The solution was treated with water [(40ML),] saturated aqueous sodium bicarbonate solution (15mL), followed by water [(40ML)] and the mixture stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and allowed to air dry overnight. The solid was heated in hexanes/ethyl acetate 2: 1, cooled to room temperature, and the crystals collected by filtration. Drying afforded the product as 6.30g of white solid (79.8% yield). [1H-NMR] [(CDC13)] ; d 7.98-7. 96 (d, [2H),] 7.70-7. 68 (d, 1H), 7.53-7. 52 (d, [1H),] 7.44-7. 43 (d, [2H),] 7.24-7. 21 (dd, 1H), 6.13 (bs, 1H), 4.67 (d, 2H), 1.60 (s, [9H).] MS: M+ +1 = 515.9/517. 9 Da.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-(aminomethyl)benzoate, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/14379; (2004); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1105187-36-7, name is Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

Methyl 3-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylate (173 mg, 0.45 mmol), 3-acetamido-phenylboronic acid (80 mg, 0.45 mmol), tetrakis triphenylphosphine palladium (0) (26 mg, 0.02 mmol) and potassium carbonate (0.45 ml, 2M aq. solution, 0.90 mmol) were mixed under nitrogen atmosphere in degassed 1,2-dimethoxyethane (4 mL). The reaction mixture was refluxed overnight. Water (10 mL) was added and the mixture was extracted with ethyl acetate (2×15 mL). After drying with MgSO4, filtering and evaporation of the solvent, the product was purified by silica gel flash chromatography (40% ethyl acetate in iso-hexane) to give the desired product (62 mg, 32% yield). ESI-MS [M+H] 395, 393; 1H NMR (400 MHz, ODd3) O 9.05 (br 5, 1 H), 7.75 (m, 1 H), 7.48 (dm, J = 7.7 Hz, 1 H), 7.39 – 7.29 (m, 2H), 7.20 (brs, 1H), 7.14 (brs, 1H), 3.80 (5, 3H), 2.13 (5, 3H).

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 1105187-36-7.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; GISING, Johan; LINDSTROM, Stefan; ANTONOV, Dmitry; BRANDT, Peter; BELFRAGE, Anna Karin; BREM, Juergen; SCHOFIELD, Christopher J.; (161 pag.)WO2018/215800; (2018); A1;,
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Some common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, 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. Recommanded Product: Diethyl 2-((phenylamino)methylene)malonate

A mixture of aniline (1a) (9.3 g, 0.1 M) and diethyl 2-(ethoxymethylene)malonate (21.6 g, 0.1 M) was heated to 110 C. After 3 hours reaction mixture was cooled and ethanol was evaporated in vacuo to afford off-white solid which was used in next reaction without further purification.The 2-phenylaminomethylene-malonic acid diethyl ester was refluxed in Dowtherm for 15 min to 2 h. The reaction mixture was cooled to 80 C. and solid was collected by filtration and washed with hexane to yield crude ethyl 4-hydroxy-quinoline-3-carboxylate 2a which was used in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54535-22-7, its application will become more common.

Reference:
Patent; Helicon Therapeutics, Inc.; US2008/306048; (2008); A1;,
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Synthetic Route of 99548-55-7, 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 99548-55-7 as follows.

Example 33B methyl 4-bromo-2-(bromomethyl)benzoate A solution of Example 33A (1.02 g, 4.47 mmol) in CCl4 (22 mL) was treated with AIBN (0.065 g, 0.4 mmol) and NBS (0.955 g, 5.4 mmol), heated to reflux for 4 hours, washed with water, dried (Na2SO4), filtered, and concentrated to provide the desired product (1.1 g, 79%).

According to the analysis of related databases, 99548-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
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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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-amino-5-bromo-2-methylbenzoate

Example 112:Methyl 5-bromo-3-(6-bromohexanamido)-2-methyl benzoateTo a stirred solution of 6-bromohexanoic acid (3 g, 15.38 mmol) in DCM (25 mL) at 0 C was added drop-wise solution of oxalyl chloride (1.481 mL, 16.92 mmol) in DCM (10 mL). After complete addition, the reaction mixture was stirred at 0 C and then at RT for 30 mm. After completion of the reaction, solvents were removed, the resulting mixture was dried and was added drop-wise to thepreviously cooled solution of methyl 3-amino-5-bromo-2-methyl benzoate (3.75 g,15.38 mmol) in DCM (30 mL). To the resulting mixture was added triethylamine(4.29 mL, 30.8 mmol) and stirred for 2 h. The reaction mixture was quenched withwater, extracted with DCM and the organic layer was washed with brine solution.The organic layer was dried over anhydrous sodium sulphate and evaporated toobtain a brown residue. The residue was purified by column chromatography(silica gel, 2:8 ethyl acetate: petroleum ether) to yield the title compound.Yield: 4.7 g (72 %); 1H NMR (DMSO-d6, 300 MHz): 6 9.56 (5, 1 H), 7.78 (d, J = 1.8 Hz, 1H), 7.68 (d, J = 1.8 Hz, 1H), 3.84 (5, 3H), 3.55 (t, J = 6.6 Hz, 2H), 2.37 (t, J = 7.2 Hz, 2H), 2.27 (5, 3H), 1 .89 (m, 2H), 1.68 (m, 2H), 1 .49 (m, 2H); MS(ESl+): m/z 422.2 [M+H], HPLC Purity: 99.56 %.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); A1;,
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Related Products of 619-42-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 619-42-1 name is Methyl 4-bromobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a sealed vial was added aniline (1.2 eq), methyl 4-(phenylamino)benzoate (1 eq), Pd(OAc)2 (0.05mmol), rac-BINAP (0.05 eq), K2CO3 (3 eq) and toluene. Then the sealed vial was irradiated in the microwave at 130C for 2h. After the reaction completed, ethyl acetate was added to dilute the reaction mixture, and then filtered by diatomite. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to afford diphenylamine intermediate (8).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Huang, Yafei; Yu, Mingcheng; Sun, Nannan; Tang, Ting; Yu, Fazhi; Song, Xiaoxia; Xie, Qiong; Fu, Wei; Shao, Liming; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 465 – 476;,
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Electric Literature of 206551-41-9, A common heterocyclic compound, 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

REFERENCE EXAMPLE 83 To a mixture of methyl 3-bromo-2-fluorobenzoate (117 mg), 2-thiopheneboronic acid (83 mg) and 1,2-dimethoxyethane (2 ml) were added a 2M aqueous solution of sodium carbonate (0.83 ml) and tetrakis(triphenylphosphine)palladium(0) (29 mg) at ambient temperature. The mixture was heated for 3 hours at 90¡ã C. After cooling, the reaction mixture was diluted with ethyl acetate (30 ml), and washed with water (20 ml*3) and brine (20 ml). The organic layer was dried over magnesium sulfate and filtered. After evaporation, the residue was chromatographed on a silica gel eluding with a mixture of ethyl acetate and n-hexane to give methyl 2-fluoro-3-(2-thienyl)benzoate (99 mg). Mass: 237 (m/z, (M+H)+) NMR(DMSO-d6, delta): 3.89 (3H, s), 7.1-7.3 (1H, m), 7.39 (1H, t, J=7.8 Hz), 7.6-7.9 (3H, m), 8.0-8.2 (1H, m).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Yamada, Akira; Spears, Glen; Hayashida, Hisashi; Tomishima, Masaki; Ito, Kiyotaka; Imanishi, Masashi; US2003/176454; (2003); A1;,
Ester – Wikipedia,
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Reference of 792-74-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A sample of 4,4′-biphenyldicarboxylate dimethyl ester, 2.0 g, was place in a 50 ml 2 neck 24/40 flask with stirring bar. Then trifluoroacetic acid, 10 ml, was added, and the mix was cooled to 0 0C. The cooled mixture was treated with 90% nitric acid, 0.38 ml, and then trifluoroacetic anhydride , 1.91 ml was added dropwise. TLC with 1 :8 ethyl acetate/hexanes on silica ant 30 minutes post TFAA showed some SM, and a new lower RF product. The mix was stirred 1 hour at 0 0C, then 3 hours at room temperature. The mixture was then poured into 100 ml of cold water, giving a gummy precipitate. The mix was treated with 80 ml of ethyl acetate and 20 ml of hexanes. The layers were separated, and the organic layer was washed with 100 ml of water. The organic layer was then stirred with 20 g of sodium bicarbonate in 100 ml of water. The ethyl acetate was evaporated in vacuo. The residue was treated with 100 ml of hexanes, heated to a boil, and diluted with ethyl acetate hot until a solution was obtained, then hexanes was added to a total volume of 200 ml. The mix was cooled to room temperature, and the resulting solids were collected by filtration, washed with 10 ml hexanes, and air dried to give 2-nitro-4,4′-biphenyldicarboxylate dimethyl ester, 1.319 g.NMR 500 MH D6DMS0: 8.51, d, J=IJ, IH, 8.31, dd, J=U, 8.1, IH, 8.06, dd, J=1.8, 8.3, 2H, 7.76, d, J=8, IH, 7.56, dd, J=1.8, 8.4, 2H, 3.94, s, 3H, 3.89, s, 3H

The synthetic route of Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMMUSOL INCORPORATED; WO2008/21745; (2008); A2;,
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