Month: March 2021

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 581065-95-4 as follows. Recommanded Product: 581065-95-4

N-Fmoc imino diacetic acid, PSMA11 , (107 mg, 0.30 mmol) was treated with PSMA12 (212 mg, 0.66 mmol), TBTU (193 mg, 0.60 mmol), HOBt (92 mg, 0.60 mmol), and DIEA (209 muIota_, 1.20 mmol) in DMF for 2 h. The reaction was concentrated in vacuo and purified through Si02 gel chromatography to afford PSMA13 (250 mg, 91 %). AP-ESI+ Mass calcd C49H75N3016: 961.51 , Found: 962.6 [M+H]+, 984.6 [M+Na]+

According to the analysis of related databases, 581065-95-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLSTICE BIOLOGICS, LTD.; BRADSHAW, Curt, W.; ELTEPU, Laxman; KABAKIBI, Ayman; LAM, Son; LIU, Bin; LIU, Dingguo; MEADE, Bryan, R.; SAKAMURI, Sukumar; WO2015/69932; (2015); A1;,
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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;,
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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. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H12O2

The 60% sodium hydride 24.4g (0.61 muM) added to the 335 ml in tetrahydrofuran, heated to 75 C. Cyclopentyl methyl formate 50g (0.39 muM) is dissolved in acetonitrile 25g (0.61 muM), slowly adding sodium hydride to the reaction solution. The completion of the dropping, 70 C reaction 15 hours, cooling, concentrated in order to remove a portion of the solvent, adding water 180 ml, extracted with ethyl acetate three times, the organic phase is discarded. The aqueous phase is 4M hydrochloric acid to pH=2, extracted with ethyl acetate three times, drying, so as to obtain bright yellow 3 – cyclopentyl -3 – oxo third nitrile (II) 49.75g, yield is 93%

According to the analysis of related databases, 4630-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Bei Ka Pharmaceutical Co., Ltd.; Wang Yong; Liu Ligang; Xiang Jie; Yang Shiqiong; Li Qian; Kang Litao; (11 pag.)CN104496904; (2017); B;,
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Reference of 70347-04-5, The chemical industry reduces the impact on the environment during synthesis 70347-04-5, name is Methyl 4-methoxy-3-methylbenzoate, I believe this compound will play a more active role in future production and life.

To a mixture of methyl 4-methoxy-3-methylbenzoate (1.0 eq) in CCl4 (0.37M), NBS (1.1 eq) and AIBN (0.2 eq) was stirred overnight at 95 C. under nitrogen atmosphere. The resulting mixture was concentrated and partitioned between DCM and water, the organic layer was dried over Na2SO4, concentrated and purified by flash chromatography on silica (eluent PE/EA=100:1 to 20:1) to give the title compound as a white solid.

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, Methyl 4-methoxy-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Apros Therapeutics, Inc.; WU, Tom Yao-Hsiang; (209 pag.)US2018/155298; (2018); 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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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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Application of 207346-42-7,Some common heterocyclic compound, 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, molecular formula is C8H7F2NO2, 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.

General procedure: Into a 500mL round bottom flask equipped with a magnetic stir bar was placed methyl 2-amino-6-methoxybenzoate (25 g, 149.6 mmol), ethanol (200 mL), cyanamide (9.43 g, 224 mmol), and concentrated HCl (6 mL). The mixture was allowed to stir at reflux for 6 hours. At one hour intervals, concentrated HCl (0.5 mL) was added. The reaction mixture was allowed to cool to room temperature and the solid, 7i, was isolated via filtration and washed with ethanol. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.88 (s, 3 H), 6.96 (dd, J=8.2, 3.1 Hz, 2 H), 7.69 (t, J=8.3 Hz, 1 H), 8.28 (br. s., 2 H), 12.67 (br. s., 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-4,5-difluorobenzoate, its application will become more common.

Reference:
Article; Pieters, Serge; McGowan, David; Herschke, Florence; Pauwels, Frederik; Stoops, Bart; Last, Stefaan; Embrechts, Werner; Scholliers, Annick; Mostmans, Wendy; Van Dijck, Kris; Van Schoubroeck, Bertrand; Thone, Tine; De Pooter, Dorien; Fanning, Gregory; Rosauro, Mari Luz; Khamlichi, Mourad Daoubi; Houpis, Ioannis; Arnoult, Eric; Jonckers, Tim H.M.; Raboisson, Pierre; Bioorganic and Medicinal Chemistry Letters; vol. 28; 4; (2018); p. 711 – 719;,
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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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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;,
Ester – Wikipedia,
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Related Products of 90030-48-1, A common heterocyclic compound, 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, molecular formula is C4H7NaO4S, 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.

Intermediate 7 Sodium 1 -methyl-3-sulfinopropanoate (282mg, 1.62mmol) was suspended in DMSO (2.5ml_). To this, (l -bromoethyl)benzene (0.185ml_, 1 .35mmol) was added and the mixture stirred at room temperature for 18 hours. The mixture was poured into water (25ml_) and extracted with diethyl ether. The organic layer was washed with brine, dried with Na2S04, filtered and concentrated in vacuo to give Intermediate 7 (309mg) as an oil. 1 H NMR (CDCIs) delta: 7.50-7.33 (5H, m), 4.23 (1 H, q), 3.68 (3H, s), 3.18-2.94 (2H, m), 2.83-2.56 (2H, m), 1 .80 (3H, d)

The synthetic route of 90030-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANTABIO SAS; LEMONNIER, Marc; DAVIES, David; PALLIN, David; WO2014/198849; (2014); A1;,
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