Month: March 2021

Reference of 4640-67-9, 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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The polyphosphoric acid 300g adding 1L the reaction bottle heating to 120 C, adding compound 3 (100g, 0.61 muM), ring octanone (161.7g, 1 . 28 muM), add 1 – ethyl -3 – methyl imidazole four fluoroborates (30g, 0.15 muM) reaction 1h, after the reaction, by adding 300 ml ice water, 1000 ml ethyl acetate, stirring 30min, then adding NaOH in and to the neutral, separating the organic layer, the organic layer dried with magnesium sulfate, filtered, the filtrate is concentrated to dry, adding isopropanol (300 ml) reflux 30min stirred and cooled to 0 C after, stirring 1h, filtered and dried to obtain white solid 4 (120g, 99.8%),

The synthetic route of 3-(4-Fluorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Yuan Shu Pharmaceutical Technology Co., Ltd; Jin, Guofan; Jin, Feng; Wang, Kai; Zheng, Bing; Fu, Yan; Jin, Zaishan; Liu, Jiongzhe; (6 pag.)CN106045909; (2016); A;,
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These common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, 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. Recommanded Product: 2032-34-0

To a solution of ethyl 1 -amino- 1 H-pyrrole-2-carboxylate lib (3.0 g, 19.46 mmol) in EtOH (100 mL) was added 3,3-diethoxypropanenitrile (25 mL, 95%, 158.23 mmol), IN HC1 (aq. 5 mL) and heated at reflux for 18 h. The reaction mixture was cooled to RT, treated with DBU (32.5 mL, 213.18 mmol), and heated at reflux for 1 h. The reaction mixture was concentrated in vacuo and the residue obtained was diluted with ethyl acetate (300 mL), extracted with water (200 mL, 150 mL). The aqueous layers were combined acidified with 4 N HC1 to pH = 1 and extracted with chloroform/methanol (3:1, 4 x 200 mL). The combined chloroform layers were dried over MgS04 filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography [silica gel 120 g, eluting with hexanes/ethyl acetate/MeOH, 1 : 1 :0 to 2:2: 1 (Rf = 0.35 with hexanes/ethyl acetate/MeOH = 2:2:1)] to furnish 4-hydroxy-[l,2-b]pyridazine-3-carbonitrile 11c (1.44 g, 47%) as a brown solid; NMR (300 MHz, DMSO- 6): delta 8.16 (s, 1H), 7.90 (dd, J= 1.6, 2.6 Hz, 1H), 7.08 (dd, J = 1.6, 4.5 Hz, 1H), 6.80 (dd, J= 2.6, 4.5 Hz, 1H); MS (ES”): 157.8 (M – H).

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

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; WU, Minwan; WO2011/150356; (2011); 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. 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3FN2O2

To a solution of 3-fluoro-4-nitrobenzonitrile (6.3 g; 37.93 mmol) and 2-bromophenol (4.4 mL; 37.94 mmol) in DMF (50 mL) was added potassium carbonate (6.29 g; 45.51 mmol). The mixture was stirred for 5 h at rt. Water (100 mL) was added, and a precipitate formed. The solid was separated via filtration, washed with water, and dried to yield 11.20 g (92.5%) of 3-(2-bromo-phenoxy)-4-nitrobenzonitrile, 1a.

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; Coats, Steven J.; Dax, Scott L.; DeCorte, Bart; Liu, Li; McDonnell, Mark; McNally, James J.; US2006/148823; (2006); A1;,
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Electric Literature of 57381-37-0,Some common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

Example 35; 5-chloro-1-[5-chloro-2-(2-oxopyrrolidin-1-yl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride; (Step 1); To a solution (139 ml) of 2-bromo-5-chlorobenzonitrile (15.0 g), pyrrolidin-2-one (7.90 ml) and cesium carbonate (45.2 g) in 1,4-dioxane were added tris(dibenzylideneacetone)dipalladium (1.59 g) and 4,5-bis(biphenylphosphino)-9,9-dimethylxanthine (2.0 g) at room temperature under a nitrogen atmosphere, and the mixture was heated under reflux for 3 hr. The mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The organic layer was filtered through celite, and washed with ethyl acetate. The filtrate was dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate_hexane=1:10?1:1) to give 5-chloro-2-(2-oxopyrrolidin-1-yl)benzonitrile (12.5 g) as yellow crystals. 1H NMR (400 MHz, CD3OD) delta ppm 2.24-2.31 (2H, m) 2.62 (2H, t, J=8.0 Hz), 3.94 (2H, t, J=6.8 Hz) 7.39 (1H, d, J=9.2 Hz) 7.60 (1H, dd, J=2.4, 8.8 Hz) 7.67 (1H, d, J=2.4 Hz).

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270393; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, 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 21803-75-8, category: nitriles-buliding-blocks

To a stirred solution of 4-annno-3-ehtorobenzonitrile (HX; 1.0 g, 6.55 mmo ) in DMF (20 mL) under argon atmosphere was added potassium O-ethylcarbonodithioate (2.62 g, 16.38 mmol)) atRT. The reaction mixture was stirred at 1 10 C for 16 h. The reaction mixture was diluted water (30 mL) and acidified using 2iV HCi to pH=2, to obtain the solid. The solid was filtered, washed with Hexane (2 x 20 mL) and dried under reduced pressure to obtain compound HY (700 mg, 3.64 nnnoL 56%) as yellow solid. *H NMR (500 MHz, DMSO-<): delta 14.3 (br s, 1H), S.24 (s, 1 H), 7.83 (dd, J= 8.1, 1.2 Hz, 1 H), 7.41 (d, J = 8. Hz. 1H). 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-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; YATES, Christopher, M.; SHAVER, Sammy, R.; HOEKSTRA, William, J.; (455 pag.)WO2017/117393; (2017); 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. 4640-66-8, name is 4-Chlorophenacylcyanide, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chlorophenacylcyanide

To a stirred solution of 3-(4-chlorophenyl)-3-oxopropanenitrile (XL; 1.5 g; 8.3 mmol) in ethanol (75 mL) was added hydrazine hydrate (0.8g; 16.7 mmol). The reaction mixture was heated to a reflux for 12 hours. The reaction mixture was cooled and concentrated underreduced pressure and then diluted with water. The aqueous layer was extracted using ethyl acetate (3 x 2OmL) and triturated with hexane to afford 3-(4-chlorophenyl)-1H-pyrazol-5- amine as a yellow solid (XLI; 1 g, 60% yield). ?H NMR (400 MHz, CDC13): oe 11.81 (bs, 1H),7.67-7.65 (d, J = 8.4 Hz, 2H), 7.42-7.40 (d, J = 8.4 Hz, 2H), 5.74 (s, 1H), 4.85 (bs, 2H). MS (M-1): 192.27.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORGINE B.V.; BAKTHAVATCHALAM, Rajagopal; BASU, Manas Kumar; BEHERA, Ajit Kumar; VENKATESHAPPA, Chandregowda; HEWSON, Christopher Alexander; KADNUR, Sanjay Venkatachalapathi; KALINDJIAN, Sarkis Barret; KULKARNI, Bheemashankar; SAXENA, Rohit; SURESH, Juluri; VISWANATHAN, Vellarkad; ZAINUDDIN, Mohd; DHARSHINIS, Akila Parvathy; KRISTAM, Rajenda; WO2015/97122; (2015); 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. 288309-07-9, name is 5-Acetyl-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 5-Acetyl-2-fluorobenzonitrile

To a stirred solution of the ketone (4-d, 106 mg, 0.65 mmol) in CH2Cl2 (5 mL) was added at 0 C dropwise [bis(2-methoxyethyl)amino]sulfur trifluoride (717 mg, 3.25 mmol). The reaction mixture was stirred at room temperature for 1 h, portioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. The crude product was diluted in MeOH (10 mL) and stirred under H2 atmosphere in the presence of Pd/C (50 mg). After 3 h, the reaction mixture was filtered and the filtrate solution was concentrated in vacuo. The crude amine was diluted with CH2Cl2 (5 mL) and reacted with 2-phenylbutanoyl chloride (119 mg) in the presence of DIEA (0.45 mL, 2.6 mmol). After 3 h, the reaction mixture was concentrated in vacuo and chromatographed (SiO2, 20% ethyl acetate in hexanes) to give the desired product (1-29); HRMS (M+1)=336.1573; 1H NMR (500 MHz, CDCl3) 7.27 (m, 7H), 7.04 (t, 1H, J=8.5 Hz), 5.78 (s, 1H), 4.47 (d, 1H, J=6.0 Hz), 3.28 (t, 1H, J=7.5 Hz), 2.21 (m, 1H), 1.82 (t, 1H, J=18.0 Hz), 0.89 (t, 1H, J=7.5 Hz)

The synthetic route of 288309-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanney, Barbara; Kim, Yuntae; Krout, Michael R.; Meissner, Robert S.; Mitchell, Helen J.; Musselman, Jeffrey; Perkins, James J.; Wang, Jiabing; US2005/277681; (2005); A1;,
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These common heterocyclic compound, 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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. Computed Properties of C8H11N

(3R)- and (3S)-3-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile[0112] To a solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine(15.0 g, 0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cisand trans isomers), followed by DBU (15 mL, 0.10 mol).The resulting mixture was stirred at room temperatureovernight. The ACN was evaporated. The mixture wasdiluted with ethyl acetate, and the solution was washedwith 1.0 N HCl. The aqueous layer was back-extractedwith three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodiumsulfate, filtered and concentrated. The crude product waspurified by silica gel chromatography (gradient of ethylacetate/hexanes) to yield a viscous clear syrup, whichwas dissolved in ethanol and evaporated several timesto remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H, 15percent ethanol/hexanes) and usedseparately in the next step to generate their corresponding final product. The final products (see Step 3) stemming from each of the separated enantiomers were foundto be active JAK inhibitors; however, the final productstemming from the second peak to elute from the preparative-HPLC was more active than its enantiomer.1H NMR (300 MHz, CDCl3): delta8.85 (s, 1H), 8.32 (s, 2H),7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H), 3.54(t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H),2.03-1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H), -0.06(s, 9H); MS(ES):437 (M+1).

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

Reference:
Patent; Incyte Holdings Corporation; FRIEDMAN, Paul A.; FRIDMAN, Jordan S.; LUCHI, Monica E.; WILLIAMS, William V.; (27 pag.)EP2349260; (2016); B1;,
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Electric Literature of 25309-65-3,Some common heterocyclic compound, 25309-65-3, name is 4-Ethylbenzonitrile, molecular formula is C9H9N, 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.

Step A. Methyl 4-ethylbenzenecarboximidoate Hydrodrochloride Hydrogen chloride gas was bubbled through a methanol solution of 4-ethylbenzonitrile (5.0 g, 38.11 mmol) at 0 C. for 30 minutes. The reaction was sealed and stood at ambient temperature overnight. The solvent was removed in vacuo and the oily residue triturated with diethyl ether. The resulting solid was removed to yield the title compound which was stored in a dry atmosphere.

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

Reference:
Patent; American Home Products Corporation; US2002/22638; (2002); A1;,
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