Category: 115279-73-7

Synthetic Route of 115279-73-7, 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 115279-73-7 as follows.

To a solution of 4-hydroxy-3-methoxy-benzoic acid (90.0 mg; 0.54 mmol) in DCM (1.8 mL) were added few drops of DMF. Oxalyl chloride (180 uL; 2.12 mmol) was added dropwise to this solution, which then was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the resulting yellow oil was dissolved in DCM (5.52 mL). This solution was added dropwise to a stirred mixture of l-(4-amino-phenyl)-cyclopentanecarbonitrile (100 mg; 0.54 mmol), prepared as in 3(B), and triethylamine (150 uL; 1.07 mmol) in DCM (4.6 mL). After stirring at room temperature for 3 hours, the solvent was evaporated under vacuum. The product was purified by preparative HPLC (Method Q), to yield the titled compound as a yellow oil (20.0 mg; 11% yield).1H NMR (300 MHz, CDC13) delta(ppm): 7.83 (br. s., 1 H), 7.64 (m, 2 H), 7.53 (d, 1 H), 7.43-7.50 (m, 2 H), 7.34 (dd, 1 H), 7.00 (d, 1 H), 3.99 (s, 3 H), 2.40-2.56 (m, 2 H), 1.84-2.17 (m, 6 H). LCMS (RT): 2.76 min (Method H); MS (ES+) gave m/z: 337.1 (MH+).

According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, 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 115279-73-7, Product Details of 115279-73-7

A mixture of 2-chloronicotinoyl chloride (50 mg) and 1-(4-aminophenyl)-cyclopentanecarbonitrile (1 eq) and K2CO3 (80 mg) in dichloromethane (20 ml) was stirred at RT for 30 min. The reaction was filtered and the filtrate was evaporated. The residue was mixed with 6-aminoindazole (150 mg) neat and heated at 210 C. for 2 hour. The reaction was cooled and purified by column chromatography to give the title compound. Mass: (M+1), 423.

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; Chen, Guoqing P.; US2004/259916; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 115279-73-7, A common heterocyclic compound, 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, molecular formula is C12H14N2, 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.

To a 500 ml four-necked flask equipped with a stirrer, a thermometer and a distillation system, 100 g of toluene and 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V) were added. 0.25 g of 4-dimethylaminopyridine, maintaining an internal temperature of 95-105 C. A solution of 12.9 g (0.05 mol) of ethyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV2) prepared in Example 4 and 30 g of toluene was added dropwise, and the mixture was dropped over 2 hours. Thereafter, the reaction was stirred at 110-115 C for 5 hours, and the formed ethanol was distilled off. After the reaction was completed, the temperature was lowered to 20-25 C, filtered, and the filter cake was washed with 20 g of toluene, the filtrate was combined, and toluene was distilled off under reduced pressure. The tert-butyl ether was recrystallized, filtered and dried to give 18.1 g of a white solid powder of eptatinib (I), yield 91.2%, liquid phase purity 99.92%, melting point 158.5-160.0 C.

The synthetic route of 115279-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 115279-73-7 as follows. Safety of 1-(4-Aminophenyl)cyclopentanecarbonitrile

To a jacketed reactor were charged 71 (1.0 equiv), 10% Pd/C (7.0 wt %), and MeOH (10 vols). The contents of the reactor were inerted with N2 and then pressurized with H2 to 6.0 bar. The jacket was initially set to 18 C. to contain the minor exotherm that ensued. After 2 h, the jacket temperature was adjusted to 35 C. to achieve an acceptable reaction rate. The reaction mixture was stirred under these conditions overnight. HPLC analysis of an aliquot of the reaction mixture revealed that conversion to the intermediate aniline was complete (<0.1% of the hydroxylamine intermediate remaining) To the reactor were then charged AcOH (1.0 equiv), formaldehyde (37% solution in MeOH, 2.7 equiv), and 10% Pd/C (3.0 wt %). The reaction mixture was again inerted with N2 and then pressurized with H2 to 6.0 bar and heated to 45 C. (0160) After 2 h, HPLC analysis indicated that the reaction was complete (<0.1% monomethyl intermediate remaining) The reaction mixture was inerted with N2 and then filtered through Celite while still at 45 C. The reactor and cake were washed with additional MeOH (2.0 vols), and the resulting filtrate was transferred to a clean jacketed reactor vessel. The solution was then distilled down to a level of 10 vols while maintaining a pot temperature of 40-50 C. (jacket temperature 55 C., 250 torr). This led to a homogenous solution at the conclusion of the distillation. The solution was then cooled to 20 C. over 1 h. Crystallization began to occur at 33 C. Water (5.0 vols) was then added dropwise over 1 h while maintaining the batch temperature at 20 C. The resulting slurry was aged overnight and then filtered. The reactor and filter cake were washed with ice-cold 1:1 MeOH:H2O (5.0 vols). After drying under vacuum at 40-45 C. to constant weight, 72 was obtained in 90% yield with an HPLC purity of 96.0% (2.8% dimer-related impurity). According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular. Reference:
Patent; Atterocor, Inc.; Hunt, III, Stephen Warren; Phillips, Martin Douglas; Matunas, Robert; Chen, Herman; Betancourt, Aimesther; Uzarama, Charles; Thibert, Roch; (31 pag.)US2016/90354; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 115279-73-7, 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 115279-73-7 as follows.

To a solution of 4-hydroxy-3-methoxy-benzoic acid (90.0 mg; 0.54 mmol) in DCM (1.8 mL) were added few drops of DMF. Oxalyl chloride (180 uL; 2.12 mmol) was added dropwise to this solution, which then was stirred at room temperature for 16 hours. The solvent was evaporated under vacuum and the resulting yellow oil was dissolved in DCM (5.52 mL). This solution was added dropwise to a stirred mixture of l-(4-amino-phenyl)-cyclopentanecarbonitrile (100 mg; 0.54 mmol), prepared as in 3(B), and triethylamine (150 uL; 1.07 mmol) in DCM (4.6 mL). After stirring at room temperature for 3 hours, the solvent was evaporated under vacuum. The product was purified by preparative HPLC (Method Q), to yield the titled compound as a yellow oil (20.0 mg; 11% yield).1H NMR (300 MHz, CDC13) delta(ppm): 7.83 (br. s., 1 H), 7.64 (m, 2 H), 7.53 (d, 1 H), 7.43-7.50 (m, 2 H), 7.34 (dd, 1 H), 7.00 (d, 1 H), 3.99 (s, 3 H), 2.40-2.56 (m, 2 H), 1.84-2.17 (m, 6 H). LCMS (RT): 2.76 min (Method H); MS (ES+) gave m/z: 337.1 (MH+).

According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 115279-73-7, 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. 115279-73-7 name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, 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.

To a 250 ml four-necked flask equipped with a stirrer, thermometer, and reflux condenser.Add 150 g of diethyl malonate, 18.6 g (0.1 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile II, and de-alcoholization reaction at 105-110 C for 4 hours (first amidation reaction) Excessive distillation of diethyl malonate was carried out under reduced pressure, cooled to 60-70 C, 13.0 g (0.12 mol) of 4-aminomethylpyridine IV was added, and the dealcoholization reaction was carried out for 4 hours at 110-115 C (second time) Amidation reaction). After cooling to 30-40 C, 80 g of isopropanol was added to the residue, recrystallized, filtered and dried to give 33.1 g of N-(4-pyridine)methyl-N’-4-(1-cyanocyclopentane) Phenylmalonamide, yield 91.3%, liquid phase purity 99.9%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Aminophenyl)cyclopentanecarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Fan Yansen; Ju Lizhu; (9 pag.)CN109810052; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 115279-73-7, The chemical industry reduces the impact on the environment during synthesis 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, I believe this compound will play a more active role in future production and life.

In a 500 ml four-necked flask equipped with a stirrer, thermometer and distillation system, add 100 g of N,N-dimethylformamide, 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V), 0.2 g of cuprous chloride. While maintaining the internal temperature between 95 and 100 C, 12.2 g (0.05 mol) of methyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV1) prepared in Example 3 and 30 g N,N-dimethylformamide were added dropwise. The solution of N,N-dimethylformamide is added dropwise in about 1 hour, after which the reaction is stirred at 100-105 C for 4 hours, and the formed methanol is distilled off, the reaction is completed, the temperature is lowered to 20-25 C, and the filter cake is used for filtration. After washing with 20 g of N,N-dimethylformamide, the filtrate was combined, and N,N-dimethylformamide was evaporated under reduced pressure. The residue was crystallized from methyl t-butyl ether, filtered and dried. 18.3 g of a white solid powder of agingatin (I) was obtained in a yield of 92.2%, a liquid phase purity of 99.96% and a melting point of 158.5-160.0 C.

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, 1-(4-Aminophenyl)cyclopentanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts