Month: March 2021

Reference of 6629-04-5,Some common heterocyclic compound, 6629-04-5, name is N-Cyanoacetylurethane, molecular formula is C6H8N2O3, 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 compound Al (3. 12g) and potassium carbonate (2.75g) in DMF (5OmL) is stirred at room temperature for 2 hours. 2.6mL carbon disulfide is added to the reaction suspension, and then kept stirring for 4 hours. After completion of the reaction, 100% ethanol is added to reaction mixture at 0C. Yellow precipitate is generated and filtered out. After washing with diethyl ether and drying under reduced pressure overnight, pale yellow solid, compound A2 is obtained in a yield of 92.3%. 1H-NMR (400MHz, DMSO-d6) 5 (ppm):14.92 (C3NHC4, s, 1H), 3.99 (C2H, q, J = 4.72Hz, 2H), 1.16 (C1H, t, J =4.72Hz, 3H). 13C- NMR (600MHz, DMSO-d6) 5 (ppm): 222.21 (C7), 164.35 (C4), 152.08 (C3), 125.16 (C6), 97.80 (C5), 59.09(C2), 14.50 (C1). HRMS (ESI) mlz calculated for C7H6N2O3S2K2+H308.9 172, found 308.9171. Formula is confirmed as C7H6N20352K2.

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

Reference:
Patent; RHODE ISLAND HOSPITAL; CHEN, Qian; YU, Hongchuan; CHEN, Yupeng; (123 pag.)WO2016/81522; (2016); A1;,
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Application of 2338-75-2, These common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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 solution of Intermediate 6a (2.0 g, 10.8 mmol) and carbon disulfide (0.71 mL, 11.8 mmol) in tetrahydrofuran (30 mL) is added dropwise to an ice cold solution of sodium hydride (950 mg of 60 % suspension in oil, 24 mmol) in tetrahydrofuran and stirred at room temperature for 3 hours. The mixture is cooled to 0 C, then methyl iodide (1.5 mL, 24 mmol) is added dropwise and stirred at room temperature for 12 hours. The mixture is poured into water andextracted with dichloromethane (2 x). The organic layers are combined, washed with brine, dried over MgSO4, filtered, concentrated and the crude material is purified by flash chromatography (hexanes/ethyl acetate gradient) to afford 3,3-bis(methylthio)-2-(4-(trifluoromethyl) phenyl)acrylonitrile I-14a.

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Azimioara, Mihai; Alper, Phil; Cow, Christopher; Mutnick, Daniel; Nikulin, Victor; Lelais, Gerald; Mecom, John; McNeill, Matthew; Michellys, Pierre-Yves; Wang, Zhiliang; Reding, Esther; Paliotti, Michael; Li, Jing; Bao, Dingjiu; Zoll, Jocelyn; Kim, Young; Zimmerman, Matthew; Groessl, Todd; Tuntland, Tove; Joseph, Sean B.; McNamara, Peter; Seidel, H. Martin; Epple, Robert; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5478 – 5483;,
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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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C3H7ClN2

Example 109(4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(chloromethyl)-4-(3-fluorophenyl)oxazolidin-2- one; [00174] To a solution of the mesylate, prepared using the methods described in example34 (35 mg, 0.07 mmol) and triethylamine (0.125 mL, 0.9 mmol) in DMF (0.3 mL) was added methylaminoacetonitrile hydrochloride (76 mg, 0.7 mmol). The reaction was heated to 90 ¡ãC and stirred for 3 h. After cooling, and dilution with water and ethyl acetate, the organic was washed successively with 1 M HCl, brine, dried over magnesium sulfate, filtered and concentrated. HPLC purification (0-90percent acetonitrile/water) gave 16 mg (53percent) of the title compound as a colorless oil. 1H NMR (acetone-d6) delta (ppm) 7.52-7.56 (m, 2H), 7.47 (ddd, IH, J = 8.1, 8.1, 6.0 Hz), 7.31-7.42 (m, 4H), 7.10-7.15 (m, IH), 6.95-6.99 (m, 4H), 5.55 (d, IH, J = 4.8 Hz), 4.75 (q, IH, J = 4.4 Hz), 4.10-4.17 (m, 2H). HPLC-MS calculated C22Hi6Cl2FNO3 (M+H+): 432.1, found: 432.1.

The synthetic route of 25808-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/76754; (2008); A2;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6574-99-8, name is 3,4-Dichlorobenzonitrile, 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 6574-99-8, Application In Synthesis of 3,4-Dichlorobenzonitrile

The solvent and catalyst recovered in Example 2 were used for feeding.1) In the reaction kettle with a reflux water separation device, add the anhydrous aprotic polar solvent 1,3-dimethylimidazoline used in Example 2 and make up 2000 kg with a new solvent.Raw materials 3,4-dichlorobenzonitrile 1000 kg, water agent 200 kg toluene, heated to 90 ~ 120 reflux, water separation for 1 to 2 hours, until the water in the kettle <0.05% 2) Add 800 kg of potassium fluoride and 45 kg of catalyst to the reaction kettle, raise the temperature to 130 150 , and reflux for 2 to 3 hours; 3) Turn on the vacuum pump, the vacuum degree is -0.1MPa, the top temperature of the reaction kettle tower is 90-115 C, and the toluene is collected, and the fractions are collected; 4) Continue to increase the temperature. When the temperature in the reactor reaches 190 200 and the top temperature reaches 170-180 , the crude 3,4-difluorobenzonitrile will be collected. When the content of 3,4-difluorobenzonitrile in the reactor is at At 89.0-89.5%, the reaction is deemed complete and the crude product is 818 kg; 5) Turn off the hot oil pump, turn on the cold oil system, the temperature in the reaction kettle drops below 100 C, put the materials in the reaction kettle into a centrifuge, the filtrate is pumped into the reaction kettle for the next feeding, and the solid materials are bagged; 6) The crude product 3,4-difluorobenzonitrile is drawn into the rectification kettle, stirring is started, and the fractions of 179-181 C are collected at elevated temperature and pressure to obtain the finished product 3,4-difluorobenzonitrile 743 kg, content 99.63%, yield 93.0%; after distillation, the residual liquid is sent to the reactor for the next feeding. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Dichlorobenzonitrile, and friends who are interested can also refer to it. Reference:
Patent; Ji’ning Kangsheng Rainbow Biological Technology Co., Ltd.; Qian Jidong; Huang Dingqian; Sheng Rui; Yan Weiwei; (8 pag.)CN110804001; (2020); A;,
Nitrile – Wikipedia,
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These common heterocyclic compound, 218632-01-0, name is 3-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. category: nitriles-buliding-blocks

[0245] A mixture of 3-fluoro-4-mtrobenzonitrile (2.85 g, 17.13 mmol), 4-(2,4- difluorophenoxy)piperidine, HC1 (3.889 g, 15.58 mmol), and ACN (19.47 mL) was heated to 80C and stirred for 12 hours, then filtered and concentrated in vacuo to afford nitro- intermediate 3-(4-(2,4-difluorophenoxy)piperidin-l-yi)-4-nitrobenzonitrile. Tlie (crude) nitro- intermediate was taken up in a 1 : 1 mixture of THF and Me OH (0.17 M, 90 mL). Ammonium chloride (12.50 g, 234 mmol) and zinc (15.28 g, 234 mmol) were added and the reaction mixture was stirred at RT for 2 hours, then filtered and concentrated in vacuo. The concentrate was diluted with water, basified with 1 M (aq) NaOH, extracted with EtOAc, dried over Na?.S04, filtered, and concentrated in vacuo to give the title compound as a viscous brown oil that solidified after 2 days (4.815 g, 94%).

The synthetic route of 3-Fluoro-4-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Nitrile – Wikipedia,
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Electric Literature of 57381-41-6, A common heterocyclic compound, 57381-41-6, name is 2,5-Dibromobenzonitrile, molecular formula is C7H3Br2N, 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.

The 5.00g (19.16mmol) 2,5- dibromobenzene cyanide, 24g (76.65mmol) 1- (4- methoxybenzyl) pyrazole boronic ester, 11.64g (76.65mmol) of cesium fluoride, 1.11g ( 0.96 mmol) tetrakis (triphenylphosphine) palladium, ethylene glycol dimethyl ether was added to 300mL 500mL three bottles, sealed, vacuum, nitrogen atmosphere, for 6 hours at 100 .After stopping the reaction, extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure, purified by silica gel column chromatography purification, 2,5-bis (1- (4-methoxybenzyl ) lH-pyrazol-4-yl) benzyl cyanide 6.5g, yield 71.33%.

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; Beijing industry university; Li, Jianrong; He, Tao; Xie, Yabo; Bai, Jinquan; (10 pag.)CN105541717; (2016); A;,
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Application of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-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.

Step D. 2-[1-(2-Cyano-4-nitro-phenyl)-piperidin-4-yl]-N-ethyl-2-phenyl-acetamide. To a solution of N-ethyl-2-phenyl-2-piperidin-4-yl-acetamide (500 mg, 2 mmol) and 2-fluoro-5-nitro-benzonitrile (337 mg, 2.03 mmol) in DMF was added K2CO3 (840 mg, 6.1 mmol). The solution was heated to 80 C. for 16 h. After cooling to rt, H2O and 3:1 EtOAc/hexanes were added. The organic portion was washed three times with H2O and once with brine, dried (Na2SO4) and concentrated to provide the title compound (yellow powder, 686 mg, 86%).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bonaventure, Pascal; Carruthers, Nicholas I.; Chai, Wenying; Dvorak, Curt A.; Jablonowski, Jill A.; Rudolph, Dale A.; Seierstad, Mark; Shah, Chandravadan R.; Swanson, Devin M.; Wong, Victoria D.; US2007/100141; (2007); 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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Aminoacetonitrile hydrochloride

To 2g (5.3mmol) C4 was added 4.42 ml (32mmol) triethylamine, 0.98g (10.6mmol) aminoacetonitrile hydrochloride, 1.22g (6.6mmol) EDCI, and 860 ml (6.6mmol) HOBT. It was dissolved in 20mL DMF. After reacting at room temperature overnight, concentrate to dry, by adding dichloromethane, with saturated sodium bicarbonate solution, salt water after washing, concentrating, methanol used for recrystallization to obtain the yellow solid, yield 90%.

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; China Pharmaceutical University; Wang, Peng; Gu, Yueqing; Huang, Jinxin; (9 pag.)(2016);,
Nitrile – Wikipedia,
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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. 3108-23-4, name is 4,4,4-Trifluoro-2-(4-fluorophenyl)-3-oxobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3108-23-4

Reagents and conditions: (a) EtONa, EtOH, refluxing; (b) CH3NHNH2, HC1, EtOH,MW, 100C, 40 mm; (c) Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoyl chloride,DCM, then DBU. A mixture of 1.8 ml (15 mmol) of ethyl 2,2,2-trifluoroacetate (ib)and 0.96 g (7.1 mmol) of 2-(4-chloro-2-fluorophenyl)acetonitrile (3a) in 10 ml ofethanol was slowly dropped into hot solution of 1.2 g of sodium in 20 ml of ethanol.The mixture was refluxed overnight. The solution turns red. After cooled down, thesolution was poured into 250 ml of cold water acidified with 10 ml concentrated HC1.The mixture was extracted with ethyl acetate. The ethyl acetate extraction was washedwith water, brine and dried over Mg504. Ethyl acetate was removed and the residualreddish oil of 4,4,4-trifluoro-2-(4-fluorophenyl)-3 -oxobutanenitrile (3c) was obtained in1.3 g. The raw material was dissolved in 10 ml of ethanol and used in next step withoutfurther purification. A mixture of 2.8 ml of the above ethanol solution and 125pi ofmethylhydrazine with 0.2 ml of concentrated HC1 was irradiated in microwave oven at100C for 40 mm. The solution was treated with saturated NaHCO3 and extracted byethyl acetate. The organic layer was washed with water, brine, dried over Mg504 andconcentrated. The yellow residue was subjected to flash chromatography purificationwith MeOHIDCM to give 165 mg of 3-(trifluoromethyl)-4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-amine (3d) as light yellow solid. ?H NMR (500 MHz, CDC13) 7.32 (s,2H), 7.14 (t, J = 8.0 Hz, 2H), 3.76 (d, J = 33.5 Hz, 3H), 3.65 (s, 2H). M/Z =260.6(M+1). To a solution of Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoyl chloride (43mg, 0.20 mmol) produced from Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoic acid(from Chem Impex International) and thionyl chloride in 10 ml of anhydrous DCM were slowly added 3 -(trifluoromethyl)-4-(4-fluorophenyl)- 1-methyl-i H-pyrazol-5 – amine obtained as described above (39 mg, 0.15 mmol) in 5 ml of anhydrous DCM. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with methanol and solvents were removed. The residue was purified via silicagel with MeOHIDCM to obtained Fmoc protected product. Fmoc protected product was dissolved in 10 ml of ethyl acetate and 0.15 mmol of DBU was added. After 20mm 20 ml of ethyl acetate was added and mixture was washed with 20 ml of water. The organic layer was collected and solvent was removed. The residue was dissolved in MeOH and acidified with 0.2N HC1. The solution was purified via preparatory RP-HPLC, elutingwith H20/CH3CN gradient (+0.05% TFA). Product fractions are collected and concentrated. The residue is dissolved in a small amount of 2M HC1 in methanol and, after concentration in vacuo, 50 mg of Compound (3) is obtained as an HC1 salt. ?H NIVIR (500 IVIFIz, MeOD) 7.40 – 7.08 (m, 6H), 7.02 (t, J = 8.8 Hz, 2H), 3.77 (d, J = 15.4 Hz, 3H), 3.37 (dt, J = 7.9, 6.6 Hz, 1H), 2.64 (m, 2H), 2.42 (m, 2H). M/Z 439.4(M+i).

The synthetic route of 3108-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; DREXEL UNIVERSITY; UNIVERSITY OF WASHINGTON; BURROWS, Jeremy; WYVRATT, Matthew; VAIDYA, Akhil; KORTAGERE, Sandhya; FAN, Erkang; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; KATO, Tomoyo; WO2015/8246; (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. 14447-18-8, name is Benzyl cyanoacetate, A new synthetic method of this compound is introduced below., Formula: C10H9NO2

2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester: To a mixture of 2,2,6-Trimethyl-heptanal (1.05 g, 6.73 mmol), piperidine (0.19 mL, 2.01 mmol) and benzyl cyanoacetate (1.29 g, 7.4 mmol) in toluene (50 mL) was added glacial acetic acid (0.72 g, 12.1 mmol). The flask was fitted with a Dean-Stark trap, and the mixture was heated at reflux for 18. The mixture was cooled, treated with dilute HCl, and the layers were separated. The organics were washed with a saturated sodium bicarbonate solution followed by brine, and dried (MgSO4), filtered and concentrated. The residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc) to give 1.3 g of 2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester m/z 314 (M+).

The synthetic route of 14447-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Field, Mark John; Williams, Richard Griffith; US2004/157847; (2004); A1;,
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