Month: July 2021

Electric Literature of 25808-30-4, 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension ofcompound 18 (147 mg, 0.67 mmol) in1,2-dichloroethane (8 mL), methylaminoacetonitrile hydrochloride (79mg, 0.74 mmol) was added at room temperature. After 5 min, DIPEA (130 muL, 0.74mmol) was added, followed by the slow addition of Na(OAc)3BH (185mg, 0.87 mmol). The reaction mixture was then heated to 70 °C and left to stirat that temperature for 24 h. Then, CH2Cl2 (10 mL) wasadded and the mixture extracted with saturated aqueous solution of NaHCO3(20 mL). The aqueous phase was further washed with CH2Cl2(2× 50 mL), the combined organic layers were dried with anhydrous Na2SO4,filtered, and evaporated under reduced pressure. The crude product was purifiedby flash column chromatography using CH2Cl2/MeOH/NH4OH= 10/1/0.1 as an eluent, to yield 80 mg (44percent) of yellow solid. Mp 116.0?117.0 °C;Rf = 0.23 (CH2Cl2/MeOH/NH4OH= 3/1/0.1); 1H NMR (400 MHz, DMSO-d6) delta 2.32 (s, 3H, CH3),3.87 (s, 2H, CH2CN), 3.95(s, 2H, CH2N), 7.17 (d, J = 8.9 Hz, 1H, Ar-H), 7.89 (d, J = 9.0 Hz,1H, Ar-H), 8.50 (d, J = 8.9 Hz, 1H, Ar-H), 9.13 (d, J = 9.0 Hz,1H, Ar-H), 11.28 (br s, 1H, OH);1H NMR (400 MHz, CDCl3) delta 2.51 (s, 3H, CH3), 3.60 (s, 2H, CH2CN),4.00 (s, 2H, CH2N), 7.22(d, J = 8.8 Hz, 1H, Ar-H), 7.88 (d, J = 8.9 Hz, 1H, Ar-H),8.59 (d, J = 8.8 Hz, 1H, Ar-H), 9.34 (d, J = 8.9 Hz, 1H, Ar-H),resonance for OH missing; 13C NMR (100 MHz, DMSO-d6) delta 41.35, 44.98, 61.32, 110.07, 115.81, 121.69,124.56, 128.52, 132.92, 135.16, 136.70, 157.79, 160.34; HRMS (ESI) m/z calculated for C11H13N4O3 [M+H]+ 273.0988, found 273.0986; HPLC purity, 95.51percent, tR = 8.66 min.

The chemical industry reduces the impact on the environment during synthesis 2-(Methylamino)acetonitrile hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sosi?, Izidor; Mitrovi?, Ana; ?uri?, Hrvoje; Knez, Damijan; Brodnik ?ugelj, Helena; ?tefane, Bogdan; Kos, Janko; Gobec, Stanislav; Bioorganic and Medicinal Chemistry Letters; vol. 28; 7; (2018); p. 1239 – 1247;,
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Adding a certain compound to certain chemical reactions, such as: 50397-74-5, name is 4-Amino-3-bromobenzonitrile, belongs to nitriles-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 50397-74-5, Computed Properties of C7H5BrN2

To a mixture of 4-amino-3-bromobenzonitrile (10.0 g, 0.050 mmol) and methyl acrylate (9.19mL, 0.101 mmol) in acetonitrile (200 mL) was added palladium acetate (0.568 g, 0.0025mmol) and tri-o-tolyl phosphine (1.54 g, 0.005 mmol) and Et3N (14.64 mL, 0.105 mmol). The reaction mixture was heated to reflux for 48 h. The reaction mass was filteredthrough celite and washed the bed with ethyl acetate. The filtrate was concentrated to afford 6.0 g of title product. ?H NMR (300 MHz, DMSO-d6): 7.92 (s, 1H), 7.82-7.77 (d, J = 15.6Hz, 1H), 7.4 1-7.38 (d, J = 8.7 Hz, 1H), 6.77-6.74(d, J = 8.7 Hz, 1H), 6.64 (s, 2H), 6.56-6.5 1 (d, J= 15.6 Hz, 1H), 3.70 (s, 3H).

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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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Related Products of 243128-37-2, 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 243128-37-2 as follows.

4-fluoro-3-methoxybenzonitrile (1 g, 6.62 mmols) was dissolved in anhydrous dichloromethane (10 mL) and cooled to 0 C. (ice-bath). To the cooled solution was added boron tribromide solution in dichloromethane (1 M, 2 eq.). The reaction mixture was stirred at 0 C. for 5 minutes, warmed to room temperature and stirred at room temperature overnight. LCMS of the reaction mixture showed some starting material was still present. Two more equivalents of boron tribromide solution was added and the reaction was stirred at RT overnight. LCMS showed that the reaction had progressed, but some starting material was still present. The reaction mixture was then heated at 45 C. overnight to complete the reaction, as confirmed by LCMS. The reaction mixture was then poured into ice-water, warmed to RT, and extracted with ethyl acetate (3*). The combined organic layer was dried over sodium sulfate, filtered and concentrated to give the crude phenol which was used in the next step without further purification.

According to the analysis of related databases, 243128-37-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ge, Min; He, Jiafang; Lau, Fiona Wai Yu; Liang, Gui-Bai; Lin, Songnian; Liu, Weiguo; Walsh, Shawn P.; Yang, Lihu; US2007/265332; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, belongs to nitriles-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 29509-06-6, Computed Properties of C6H9NO

A solution of 4-meroyl-3-oxorhoentanenitrile (Compound [CCLXJ) (8.8 g, 79.2 mmol, 1.00 equiv) and NH2NH2 H2O (80%, 7.5 g, 120 mmol, 1.50 equiv) in ethanol (300 mL) was heated to reflux for 1 h under nitrogen. After removed the solvent under vacuum, the residue was loaded onto a silica gel column with dichloromethane/methanol as an eluent to give Compound [CCLXIJ as a yellowish oil: LC-MS m/e 126 (M+H) +; 1H NMR (300 MHz, DMSO- d6) delta ppm 5.17 (s, 1H), 2.75 (septet, J = 6.9 Hz, 1H), 1.14 (d, J = 6.9 Hz, 6H).

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BANYU PHARMACEUTICAL CO., LTD.; FAN, Weiming; HAXELL, Thomas, F. N.; JENKS, Matthew, G.; KAWANISHI, Nobuhiko; LEE, Shuliang; LIU, Hao; MALASKA, Michael, J.; MOORE, Joseph, A., III; OGINO, Yoshio; ONOZAKI, Yu; PANDI, Bharathi; PEEL, Michael, R.; SAKAMOTO, Toshihiro; SIU, Tony; WO2010/104933; (2010); 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 67832-11-5 as follows. Product Details of 67832-11-5

[0114] To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL), BH3 THF (45 mL, 45 mmol) was added. The solution was stirred at 0 C for 1 h and heated to 80 C for 16 h. Then the mixture was quenched with MeOH. After concentrated, the residue was stirred with saturated HCl/EtOAc solution and filtered. The filter cake was rinsed with ether (20 mL x3) and dried under vacuum to afford (4-bromo-2-methylphenyl)methanamine (3.2 g, yield: 90%) as white solid. ESI-MS (M+H)+: 200.1 Preparation of tert-butyl 4-bromo-2-methylbenzylcarbamate

According to the analysis of related databases, 67832-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN MA INC.; MACPHEE, J. Michael; CHEN, Robbie; FERGUSON, Steven; FRANKLIN, Lloyd; MACK, Tamera, L.; (78 pag.)WO2016/201271; (2016); A1;,
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Electric Literature of 1080-74-6, These common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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.

2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile (2 g, 10.30 mmol, M = 194.19 g/mol) andfurfural (0.99 g, 0.85 mL, 10.30 mmol, M = 96.08 g/mol, d = 1.16) were dissolved in ethanol (50 mL)and the solution was heated at 80 C for 5 min. An orange precipitate formed. After cooling, it wasfiltered off, washed several times with ethanol, then pentane and dried under vacuum (2.33 g, 83%yield, orange solid).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bonardi, Aude-Heloise; Dumur, Frederic; Duval, Sylvain; Gigmes, Didier; Lalevee, Jacques; Noirbent, Guillaume; Xu, Yangyang; Molecules; vol. 25; 10; (2020);,
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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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4592-94-3

General procedure: To a solution of 0.45 g of 3-(4-bromophenyl)-3-oxopropanenitrile (6a, 2.0 mmol) in 25 mL of ethanol, 0.165 g of benzothiazolylhydrazine (5a, 1.0 mmol) and 0.058 g of propionaldehyde (8a, 1.0 mmol) were added along with 2 drops of conc. HCl. The reaction mixture was heated to reflux for 45 minutes until the formation of a solid product in the reaction mixture. The hot reaction mixture was filtered at the vacuum pump and washed with hot ethanol to afford the pure compound 7a. All other compounds (7b-i) were synthesized according to the procedure mentioned for 7a using heteroarylhydrazines (5a-c), different 3-aryl-3-oxopropanenitriles (6a-d) and aldehydes (8a-d). 1-(Benzo[d]thiazol-2-yl)-4,7-dihydro-4-ethyl-3,6-di(4-bromophenyl)-1H-pyrazolo[3,4-b]pyridine-5-nitrile (7a). Yield 62%; M.p. 240-245 C; IR (KBr, cm-1): 2208 (CN), 3340 (N-H); 1H NMR (400 MHz, CDCl3): delta 0.87-0.90 (t, 3H, CH3, J 6.8 Hz), 1.71-1.89 (m, 2H, CH2), 4.44-4.46 (t, 1H, 4-H, J 4 Hz), 7.38-7.42 (m, 1H, 6?-H), 7.48-7.51 (m, 1H, 5′-H), 7.62-7.69 (m, 6H, Ph-H), 7.72-7.74 (m, 2H, 2??-H), 7.78-7.80 (d, 1H, 7′-H, J 8.0 Hz), 7.86-7.88 (d, 1H, 4′-H, J 8.0 Hz), 9.1 (s, 1H, exchangeable with D2O, 7-H); 13C NMR (75 MHz, CDCl3): delta 8.8, 28.2, 36.6, 84.7, 99.5, 121.7, 121.9, 123.4, 125.1, 125.4, 126.8, 128.7, 129.3, 130.9, 131.5, 132.0, 132.6, 139.9, 148.4, 150.3, 160.7; MS: m/z 615.97 [M+1]+, 617.97 [M+1+2]+, 619.97 [M+1+4]+, (1:2:1); Elemental analysis: Calcd. for C28H19Br2N5S: C, 54.47; H, 3.10; N, 11.34; Found: C, 53.35; H, 2.63; N, 11.12.

The synthetic route of 4592-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aggarwal, Ranjana; Kumar, Suresh; Singh, Gulshan; Synthetic Communications; vol. 49; 7; (2019); p. 973 – 985;,
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Electric Literature of 159847-81-1, 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. 159847-81-1 name is Methyl 2-amino-5-cyanobenzoate, 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.

Methyl [2-AMINO-5-CYANOBENZOATE] (5.0 g, 28.41 mmol) was dissolved in MeOH (105 mL). Then 6M [NAOH] (14 mL) was added. The resulting mixture was stirred at RT O/N. The reaction mixture was diluted with H20 (143 mL), washed with DCM to remove any unreacted S. M. The product was precipitated from aqueous layer by addition of conc. [HC1] to pH 1 and extracted with EtOAc (3 x 100 mL). The combined organic layers were dried over MgS04 Solid was removed by filtration, and filtrate was concentrated to dryness under reduced pressure. The light yellow product was obtained in the yield of 94%. [‘H NMR] (300 MHz, DMSO-d6) 8 8.08 (d, 1H), 7.56 (dd, [1H),] 7.50 (br), 6.85 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-cyanobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18428; (2004); A1;,
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These common heterocyclic compound, 34667-88-4, name is 2-Fluoro-4-nitrobenzonitrile, 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. Product Details of 34667-88-4

To 2-fluoro-4-nitrobenzonitrile (8.5 g, 51.2 mmol) was added 10% palladium on carbon (0.5 g) and EtOAc (42.5 mL) and EtOH (170 mL) and the reaction was hydrogenated at 50 psi for 1 h. The reaction was filtered through Celite and the reaction mixture was concentrated to afford 6.7 g (96% yield) as a light brown solid. LCMS m/z 135.1[M + H]+.

The synthetic route of 2-Fluoro-4-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/157162; (2008); 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 455-18-5 as follows. Safety of 4-(Trifluoromethyl)benzonitrile

General procedure: Benzonitrile 1a (1 mmol), Na2S*9H2O (1.2 mmol) and DMF (1 mL) were added into a 10 mL bottle. The reactor was placed in a heating magnetic stirrer at 130 C. After 2.5 h, by adding about 3 mL H2O after the reaction to disperse the solid product, the reaction mixture was extracted with EtOAc (3 x 3 mL), and the mixture was purified by column chromatography.

According to the analysis of related databases, 455-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cao, Xian Ting; Yang, Huiyong; Zheng, Hui; Zhang, Pengfei; Heterocycles; vol. 96; 3; (2018); p. 509 – 517;,
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