Author: Jessica.F

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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, A new synthetic method of this compound is introduced below., Product Details of 115279-57-7

10556] The above reaction scheme illustrates the synthesis of a compound of the invention 2-13. Methylation of starting material 2-1 yields compound 2-2, which is subsequently reduced to the amine 2-3. In a separate reaction, compound 2-4 is converted to a salt, such as an HC1 salt, which is then reacted, for example, with 2-nitrovinyl-hydroxylamine to yield compound 2-6. Further cyclization yields compound 2-7. Halogenation with a reagent such as POd3 results in compound 2-8, which can be coupled with intermediate 2-3 to yield 2-9. The nitro moiety of 2-9 is subsequently reduced to an amine, and a further reaction with 4-nitrophenyl carbonochloridate results in the heterocycle 2-11. The desired compound 2-13 is then prepared by coupling to the benzoxazolyl boronate 2-12, for example in a Suzuki coupling.

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; Intellikine LLC; Ren, Pingda; Liu, Yi; Li, Liansheng; Chan, Katrina; Wilson, Troy Edward; Campbell, Simon Fraser; US2015/320727; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 5922-60-1, name is 2-Amino-5-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 5922-60-1, Quality Control of 2-Amino-5-chlorobenzonitrile

1) Synthesis of (2-amino-5-chlorophenyl)cyclopropyl) methanone 2-Amino-5-chlorobenzonitrile (500 mg, 3.28 mmol) was dissolved in THF (10 mL), and while stirring the reaction solution at 0°C, cyclopropyl magnesium bromide (0.5 M THF solution, 26.4 mL) was added dropwise thereto. The reaction solution was stirred overnight under heating at 80°C, followed by ice-cooling, and 2 N hydrochloric acid was added thereto under ice-cooling. After the reaction solution was stirred at room temperature for 2 hours, the solution was diluted with ethyl acetate and then neutralized with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated and washed with saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane = 3/1), whereby (2-amino-5-chlorophenyl) (cyclopropyl) methanone (453 mg, 83percent) was obtained as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 0.98-1.03 (2H, m), 1.16-1.20 (2H, m), 2.54-2.60 (1H, m), 6.61 (1H, d, J = 8.8 Hz), 7.21 (1H, dd, J = 8.8, 2.4 Hz), 7.92 (1H, d, J = 2.4 Hz)

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

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2210880; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4, category: nitriles-buliding-blocks

Stage 2: 6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide 6-Chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid (2.74 g, 5.07 mmol, 86% pure) was dissolved in N,N-dimethylformamide (14 ml), and 1-aminocyclopropanecarbonitrile hydrochloride (0.78 g, 6.59 mmol), N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate (2.12 g, 5.07 mmol) and 4-methylmorpholine (1.54 g, 15.2 mmol) were added. The reaction mixture was stirred at room temperature for 16 h and then ethyl acetate was added. The organic phase was washed with hydrochloric acid (1 mol/l) and the aqueous phase was once again extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and the portion which was insoluble in both phases was filtered off. The filtercake is triturated with boiling ethyl acetate (15 ml) and the precipitate is washed with warm ethyl acetate. This leaves 2.01 g (74% of theory) of 6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide. HPLC-MS: logP=3.12; mass (m/z): 529.0 (M+H)+; 1H NMR (D6-DMSO): delta 1.25-1.29 (m, 2H), 1.56-1.60 (m, 2H), 6.30-6.38 (m, 1H), 7.50 (s, 1H), 7.57 (s, 1H), 7.70-7.74 (m, 1H), 7.82-7.86 (m, 2H), 8.07-8.09 (m, 1H), 8.21 (s, 1H), 9.30 (s, 1H), 9.73 (d, 1H), 12.07 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Intellectual Property GmbH; Heil, Markus; Heilmann, Eike Kevin; Holmwood, Graham; Jeschke, Peter; Maue, Michael; Kapferer, Tobias; Reidrich, Matthias; Becker, Angela; Malsam, Olga; Losel, Peter; Voerste, Arnd; Goergens, Ulrich; Andree, Roland; US2014/88167; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 199536-01-1, A common heterocyclic compound, 199536-01-1, name is Methyl 3-amino-5-cyanobenzoate, molecular formula is C9H8N2O2, 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.

CH3SO2Cl (40 mmol) was added to the solution of methyl-3-amine-5-cyanobenoate (10 mmol), pryridine (50 mmol) and DMAP (1 mmol) in DCM (150 mL). The solution was then heated to reflux for 4 hours. After cooling, diluted hydrochloric acid was poured into the solution. The organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated. The crude product was purified by column chromatography to afford methyl-3-cyano-5-(methylsulfonamido)benoate in 70% yield.

The synthetic route of 199536-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hutchison Medipharma Enterprises Limited; US2009/118292; (2009); 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. 19179-31-8, name is 3,5-Dimethoxybenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3,5-Dimethoxybenzonitrile

3,5-Dimethoxy-benzamidine Dry HCl gas was bubbled through a cooled (-15 C.) solution of 3,5-dimethoxybenzonitrile (1.50 g, 9.20 mmol) for 30 minutes. The reaction mixture was placed in a refrigerator overnight. After evaporation of the solvent, a white solid was obtained which was dissolved in ethanol.

The synthetic route of 19179-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer, Markus; Loeffler, Bernd Michael; Peters, Jens-Uwe; Steger, Matthias; Weiss, Peter; US2003/216382; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6136-68-1, name is 3-Acetylbenzonitrile, 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 6136-68-1, COA of Formula: C9H7NO

Example C7: Methyl 3- 3-cyanop eny -3-oxopropanoate: [0151] Into a three-necked flask equipped with an argon inlet and a condenser were placed sodium hydride (60%>, 689.5 mg, 17.23 mmol), dimethyl carbonate (1.55 g, 17.23 mmol) and 15 mL of toluene. The mixture was stirred under reflux and a solution of 3- acetylbenzonitrile (1.0 g, 6.19 mmol) in toluene (15 mL) was added drop wise. The reaction mixture was stirred at 100C for 2h. The reaction mixture was monitored by LCMS and purified by column chromatography on silica gel eluted with 0-10% of ethyl acetate in petroleum ether to give the product (1.2 g, 86%>).

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; BRAINCELLS, INC.; HUTCHINSON, John Howard; BLEICHER, Leo; COSFORD, Nick; ARDECKY, Robert John; ZOU, Jiwen; WO2013/33246; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

5922-60-1, name is 2-Amino-5-chlorobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C7H5ClN2

N-(4-Chloro-2-cyanophenyl)-2-(5-morpholin-4-ylbenzimidazol-2-yl)acetamide LiHMDS (2.5 equivalents) was added to ethyl 2-[5-(2-morpholin-4-ylethoxy)benzimidazol-2-yl]acetate (1.0 equivalent) in THF at -78° C. After 1 hour, 2-amino-5-chlorobenzenecarbonitrile (0.82 equivalents) in THF was added. The reaction was allowed to warm to 23° C. and stirred overnight. The resulting mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to give the desired product. LC/MS m/z 396.1 (MH+), Rt 1.79 minutes. N-(4-chloro-2-cyanophenyl)-2-(5-morpholin-4-ylbenzimidazol-2-yl)acetamide (1.0 equivalent) was heated in NaOMe (0.5 M in MeOH, 18 equivalents) at 70° C. for 2 hours. The resulting mixture was cooled, and the resulting solid was filtered and washed with water to give the desired product. LC/MS m/z 396.4 (MH+), Rt 2.13 minutes.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiron Corporation; US2005/261307; (2005); 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. 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-5-trifluoromethylbenzonitrile

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C. for 21/2 hours. The reaction mixture is cooled and poured into de-ionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

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; Rohm and Haas Company; US4419122; (1983); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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.

N-(4-Cyano-2-methoxyphenyl)formamide Acetic anhydride (0.65 mL, 6.7mmol) was cooled in an ice bath and formic acid (0.38 mL, 10 mmol) was added with stirring. The ice-bath was removed and the mixture was stirred for a further 60 minutes. The reaction was re-cooled in the ice-bath and 4- amino-3-methoxybenzonitrile (0.25 g, 1.58 mmol) was added. The reaction was stirred at ice-bath temperature for 5 minutes, then at room temperature for 60 minutes. The reaction was concentrated in vacuo, azeotroped with toluene and the title compound was precipitated from ether/hexanes as a white powder (255 mg, 71.3%). 1 H NMR (500 MHz, DMSO-d6): delta 10.07 (s, 1 H), 8.39 (s, 1 H), 8.37 (s, 1 H), 7.52 (d, J = 1.7 Hz, 1 H), 7.4 (dd, J = 8.4, 1 .8 Hz, 1 H), 3.92 (s, 3H). LCMS (ESI) R, = 1 .76 minutes MS m/z 177 [M+H]+

The synthetic route of 177476-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, Quality Control of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

A, To 40g citalopram diol intermediate free alkali crystal prepared in Example 1 (purity: 99.9%, HPLC, area normalization method), 360ml isopropanol was added and the solution was heated until the crystal was dissolved entirely. 23.6g D-di-4-methylbenzyol tartaric acid was added and dissolved, the solution was placed at room temperature for 12 hours. The crystal crystallized and was filtrated, washed with small amount of isopropanol to give S-citalopram diol intermediate—D-di-4-methylbenzyol tartaric acid salt crystal. The obtained salt was then suspended and mixed in toluene, added with NaOH solution and stirred. The solution was placed aside, the organic and inorganic layer was separated. The toluene layer was heated, concentrated under vacuum to give 14g S-citalopram diol intermediate oil substance (yield: 70%, purity: 99.9%), in which there was 0.5% R-citalopram diol intermediate (chiral HPLC).

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; Hangzhou Minsheng Pharm. Co., Ltd.; EP1700851; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts