Category: nitriles-buliding-blocks

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. 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(4-Chloro-3-methoxyphenyl)acetonitrile

(4-Chloro-3-hydroxy-phenyl)acetonitrile BBr3 (17 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in dichloromethane (120 mL) at -78 C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (40 mL*3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) delta 7.34 (d, J=8.4 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 2H).

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; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); 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. 508203-48-3, name is 2,3-Difluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 508203-48-3

To a suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmcl) in ethanol (111 mL) at25C was added hydroxylamine hydrochloride (4.5 g, 65.3 mmol). The reaction mixture was heated at80C for 2 hours. After cooling to room temperature, the volatiles were removed under reduced pressurethus affording a white solid that was used in the next transformation without purification.1H NMR (400 MHz, CDCI3) oe ppm: 7.30 (m, 1H), 6.95 (m, 1H), 6.50 (brs, 1H), 5.05 (brs, 2H),2.30 (s, 3H).

According to the analysis of related databases, 508203-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (161 pag.)WO2018/177894; (2018); 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 133541-45-4 as follows. Computed Properties of C7H2BrF2N

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173 g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-l,l,l- trifluoropropanol [CAS 3539-97-7] dropwise (52.4 g, 460 mmol). The resulting mixture was heated at 70 C for for 15 hours and cooled to room temperature. The reaction was concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3x). The combined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to give the desired product as a white solid (90.3 g, 93% purity, 64% yield). LC-MS (Method A): R, = 1.29 min; MS (ESIpos): m/z = 312.0 [M+H]+. 1H-NMR (400 MHz, CHLOROFORM-d) d [ppm] : 1.511 (4.41), 1.531 (15.64), 1.533 (16.00), 1.548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1.01), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

According to the analysis of related databases, 133541-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; JANZER, Andreas; POLITZ, Oliver; EHEIM, Ashley, Lakner; (87 pag.)WO2019/197269; (2019); 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. 4387-32-0, name is 2-Chloro-5-methylbenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-5-methylbenzonitrile

To a solution of 2-chloro-5-methyl-benzonitrile (9.0 g, 59.4 mmol) in anhydrous THF (90 mL) at 0 C was added BH3-THF (1.0 M, 178 mL, 178 mmol) dropwise under a nitrogenatmosphere. The mixture was stirred at room temperature for 12 h. The reaction was quenched with 2N HC1 (110 mL) at 0 C and then heated to 70 C for 1 h. After cooling the reaction to room temperature, the solution was washed with DCM (150 mL). The aqueous phase was basified with iN NaOH to pH 8 and then extracted with DCM (150 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give thetitle compound (5.8 g, 63%) as yellow oil. ?HNMR (400 IVIFIz, CDC13) 7.22 (d, J 8.0 Hz,1H), 7.17 (s, 1H), 6.99 (d, J= 8.0 Hz, 1H), 3.88 (s, 2H), 2.32 (s, 3H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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Application of 34662-24-3, A common heterocyclic compound, 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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 c) intermediate 11Synthesis of 2-[(2-hydroxyethyl)amino]-3-nitrobenzonitrile2-chloro-3-nitrobenzonitrile (74g, 0.408 mol) is mixed with ethanol (370 ml) and ethanolamine (57 ml). The mixture is stirred for 16 hrs at room temperature. To complete the reaction, the mixture is refluxed for 2 hours. After cooling, the mixture is concentrated under vacuum; the product precipitates as a red solid. To eliminate the ethanolamine hydrochloride salt, the suspension is triturated with 500 ml of water and filtrated under vacuum. The solid is washed with ethanol and ether then dried to give the desired product (75g, 89%).IH NMR (300MHz, DMSO-d6) delta ppm 3.55-3.60 (m,2H) 3.69-3.74 (m,2H) 6.75 (dd, 7=7.63, 8.52 Hz, 2H) 7.90 (dd, /=7.63, 1.76 Hz, 2H) 8.27 (dd, /=8.52, 1.76 Hz, IH) 3.35 m, IH)

The synthetic route of 34662-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
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Electric Literature of 906673-45-8, These common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, 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.

Compound IV (5.00 g, 16.4 mmol, 1.0 eq) and DHP (2.07 g, 24.6 mmol, 1.5 eq) was dissolved in dichloromethane (40 mL). p-Toluenesulfonic acid (0.28 g, 1.6 mmol, 0.1 eq) was added, and the reaction mixture was stirred. After 5h, TLC showed that the basic reaction of the raw materials was completed, post-processing was carried out, the reaction mixture was quenched by the addition of 50 mL of aqueous sodium hydrogencarbonate solution, extracted with 50 mL of dichloromethane, liquid separation was carried out, the organic phase was washed, dried, concentrated, and the obtained crude product was purified by column chromatography to yield 5.71 g of a yellow oil in a yield of 89%.

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Wangshanwangshui Bio-pharmaceutical Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute Suzhou Pharmaceutical Chuangxin Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Tian Guanghui; Wu Jianzhong; Yu Jianghui; Pang Zhenqiang; Li Junyong; (10 pag.)CN108047261; (2018); A;,
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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 175596-01-7 as follows. Recommanded Product: 175596-01-7

Preparation 91 4-Aminomethyl-2-fluoro-benzoic acid methyl ester Add a slurry of Raney nickel in ethanol (1.2 g, 1.2 ml) to 4-cyano-2-fluoro-benzoic acid methyl ester (5.8 g, 30.0 mmol) in 2N ammonia in methanol (580 mL). Purge with nitrogen gas (3*), purge with hydrogen gas (3*), and pressurize with hydrogen gas to 419 KPa. Heat the reaction at 40 C. for 18 hrs. Allow to cool to room temperature and filter the reaction mixture. Concentrate the filtrate to the crude title compound (6.9 g, 99%). MS (m/z): 184 (M+1).

According to the analysis of related databases, 175596-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 86770-80-1, name is 3,3-Difluorocyclobutanecarbonitrile, 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 86770-80-1, category: nitriles-buliding-blocks

EXAMPLE 20 Preparation of 1-(3-chloropyridin-2-yl)-3,3-difluorocyclobutanecarbonitrile To a 100 mL round bottom flask was added 2,3-dichloropyridine (2.9 g, 20 mmol), 3,3-difluorocyclobutanecarbonitrile (2.1 g, 18 mmol), and toluene (50 mL). The mixture was cooled to C. and sodium hexamethyldisilazide (NaHMDS, 2.0 M in THF, 11 mL, 22 mmol) was added. The reaction mixture was warmed to rt and stirred for 2 h. The mixture was then diluted with EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, and concentrated to provide the desired product (3.4 g) as a colorless oil.

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; Cytokinetics, Inc.; Ashcraft, Luke W.; Bergnes, Gustave; Collibee, Scott; Chuang, Chihyuan; Gardina, Jeff; Morgan, Bradley P.; Muci, Alex R.; Qian, Xiangping; Romero, Antonio; Warrington, Jeffrey; Yang, Zhe; US9133123; (2015); B2;,
Nitrile – Wikipedia,
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Related Products of 13726-21-1, These common heterocyclic compound, 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, 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 third process; (4-Chloro-3-methoxyphenyl) acetic acid methyl ester; Potassium hydroxide (5.86 g) was dissolved in water (25 ml) and the mixture was added to a solution of 4-chloro-3-methoxyphenylacetonitrile (3.80 g) in ethanol (80 ml) at room temperature. The reaction solution was refluxed for 1.5 hours. After cooling, concentrated hydrochloric acid (8.8 ml) and water (50 ml) were added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (100 ml) and concentrated sulphuric acid was added thereto. The mixture was refluxed for 1.45 hours. After cooling, the reaction solvent was evaporated under reduced pressure and water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give a title compound (4.43 g). The yield was 99 %. 1H-NMR (CDCl3) delta: 3.61(2H,s), 3.71(3H,s), 3.91(3H,s), 6.81(1H,dd,J=1.8,8.1Hz), 6.87(1H,d,J=1.8Hz), 7.30(1H,d,J=8.1Hz).

The synthetic route of 13726-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi Co., Ltd.; EP1887000; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 2-(4-cyanophenyl)acetate

Step 0 (Intermediate A): Chlorosulfonylisocyanate (10 g, 70.65 mmol) was added to a solution of t-butanol (6.74 mL, 70.65 mmol) in dichloromethane (50 mL) at 0 C. and stirred for 15 min. Dimethylaminopyridine (8.63 g, 70.63 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The mixture was partitioned between water (200 mL) and dichloromethane (100 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (100 mL). Combined organic layer was washed with water (4×200 mL) and brine (500 mL), dried over sodium sulfate and concentrated. Crude compound was recrystallized with acetonitrile (130 mL) to afford N-(1-(tert-butoxycarbonyl)sulfamoyl)pyridine-4(1H)-ylidene)-N-methylmethanaminium (A) (9.5 g, 45%) as a white solid.[0567]Step 1: Ethyl 2-(4-cyanophenyl)acetate (4.0 g, 21.14 mmol) in tetrahydrofuran (20 mL) was added to a suspension of 60% sodium hydride (850 mg, 21.14 mmol) in tetrahydrofuran (20 mL) at 0 C. and stirred for 30 min. Methyl iodide (1.36 mL, 21.14 mmol) was added at 0 C.; reaction mixture was then stirred at room temperature for 4 h. Reaction mixture quenched with saturated NH4Cl solution (20 mL), diluted with water (200 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers was washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, and evaporated to get crude, which was purified by column chromatography (silica gel; 60-120 mesh); the product eluted with 10% ethyl acetate in pet ether to yield ethyl 2-(4-cyanophenyl)propanoate (3.2 g, 75%) as colorless liquid.[0568]Step 2: 20% Pd/C (1.2 g) and di-tert-butyl dicarbonate (12.89 mL, 57.97 mmol) were added to a solution of ethyl 2-(4-cyanophenyl)propanoate (6.0 g, 28.98 mmol) in ethanol (60 mL) and hydrogenated at 60 psi at room temperature for 18 h. Reaction mixture was filtered through celite, washed with methanol (100 mL) and concentrated to give ethyl 2-(4-((tert-butoxycarbonylamino)methyl)phenyl)propanoate (6.0 g, 67%) as off white solid.[0569]Step 3: Trifluoroacetic acid (6 mL) was added to a solution of ethyl 2-(4-((tert-butoxycarbonylamino)methyl)phenyl)propanoate (6.0 g, 19.54 mmol) in dichloromethane (30 mL) at 0 C. and stirred for 4 h at room temperature. The volatiles were evaporated under reduced pressure, basified with saturated NaHCO3 and extracted with ethyl acetate (3×50 mL). Combined organic layers washed with water (100 mL), brine solution (50 mL), dried over sodium sulfate and concentrated to give ethyl 2-(4-(aminomethyl)phenyl)propanoate (3.5 g, 86%) as colorless liquid.[0570]Step 4: N-(1-(tert-butoxycarbonyl)sulfamoyl)pyridine-4(1H)-ylidene)-N-methylmethanaminium (A) (5.81 g, 19.32 mmol) was added to a suspension of ethyl 2-(4-(aminomethyl)phenyl)propanoate (4.0 g, 19.32 mmol) in dichloromethane (40 mL) at room temperature and stirred for 16 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×75 mL). Combined organic layer was washed with water (50 mL), brine (50 mL), dried over sodium sulfate and concentrated to get crude compound, which was purified by column chromatography (silica gel; 100-200 mesh). The product eluted with 20% ethyl acetate in pet ether to yielded ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate (3.8 g, 51%) as pale yellow solid.[0571]Step 5: Lithium hydroxide monohydrate (826 mg, 19.68 mmol) in water (10 mL) was added to a solution of ethyl 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoate (3.8 g, 9.84 mmol) in tetrahydrofuran (30 mL) at 0 C. and stirred at room temperature for 18 h. The volatiles were evaporated; the residue diluted with water (50 mL) and extracted with diethyl ether (2×20 mL). The aqueous layer was acidified (pH ?5) with acetic acid at 0 C., precipitated solid was filtered and dried under reduced pressure to afford 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoic acid (2.3 g, 56%) as white solid.[0572]Step 6: 2-(4-((N-(tert-butoxycarbonyl)sulfamoylamino)methyl)phenyl)propanoic acid (269 mg, 0.751 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (200 mg, 0.751 mmol) were dissolved and mixed in tetrahydrofuran (5.8 mL), followed by addition of N-hydroxybenzotriazole (103 mg, 0.751 mmol) and O-(1H-benzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium tetrafluorborat (238 mg, 0.751 mmol) and N-ethyldiisopropylamine (0.338 mL, 2.25 mmol). The reaction mixture was stirred for overnight at room temperature and then quenched by water and extracted with ethyl acetate. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamatein pure form (258 mg, 57%).[0573]Step 7: To a solution of tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (250 mg, 0.412…

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; Gruenenthal GmbH; Frank, Robert; Bahrenberg, Gregor; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/79377; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts