Category: 115279-57-7

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., category: nitriles-buliding-blocks

Example 1f 2-[4-(6-Bromo-3-nitro-quinolin-4-ylamino)-phenyl]-2-methyl-propionitrile 18 g (62.6 mmol) of 6-bromo-4-chloro-3-nitro-quinoline (Example 1c) and 11 g (68.9 mmol) of (2-(4-amino-phenyl)-2-methyl-propionitrile (Example 1e) are dissolved in 350 ml of acetic acid and stirred for 2 h. After this time, water is added and the yellow precipitate is filtered off and washed with H2O. The solid is dissolved in EtOAc-THF (1:1), washed with sat. aqueous NaHCO3 and dried over MgSO4. The organic phase is evaporated to dryness to give the title compound as a yellow solid. ES-MS: 411, 413 (M+H)+, Br pattern; analytical HPLC: tret=3.69 min (Grad 1).

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.

Electric Literature of 115279-57-7, 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. 115279-57-7 name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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.

Step D Synthesis Route B Amine V (crude product; 695 mg, 3.76 mmol) and nitrile IX (414 mg, 2.58 mmol) is suspended in dichloromethane (16 ml) under an N2 protective-gas atmosphere. 4-Methylmorpholine (0.6 ml, 5.46 mmol) is added. Bis(tri-chloromethyl) carbonate X (460 mg, 1.55 mmol) dissolved in dichloromethane (3 ml) is added dropwise over the course of about 15 min. at room temperature. The reaction solution is stirred at room temperature for a further 1.5 h. Water (30 ml) is added to the reaction mixture, which is then stirred vigorously for 10 min. The organic phase is separated, washed twice with water and dried using Na2SO4. The solvents are removed under reduced pressure in a rotary evaporator, giving 730 mg of crude product. The crude product is purified by means of column chromatography (80 g of Si60, CH2Cl2/5% MeOH), and the suitable fractions are combined. Removal of the solvents gives imidazolone XI (279 mg, 0.79 mmol, 51% yield) as yellow solid (see step E for the further processing of the crude mixture). Analytical data of imidazolone XI: TLC: Rf=0.31 (Si60, CH2Cl2/4% MeOH/1% NH3); m.p.: 167 C.; LC-MS: tR=2.056 min (UV=220 nm), tR=2.063 min. (TIC, with [MH]+=353); 1H NMR (400 MHz, DMSO) delta 8.40 (d, J=5.3, 1H), 7.63-7.55 (m, 2H), 7.51 (s, 1H), 7.39-7.29 (m, 3H), 7.15 (d, J=1.8, 1H), 3.35 (s, 3H), 1.74 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Aminophenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2012/220587; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(4-Aminophenyl)-2-methylpropanenitrile

To a solution of compound 1 (4.3 g, 15 mmol) in acetic acid (100 mL) at 250C, was added 2-(4-aminophenyl)-2-methylpropanenitrile (2.4 g, 15 mmol). The reaction mixture was stirred at 250C for 30 mins. The reaction mixture was quenched with ice-water and the solid was filtered, washed with 10% cold aqueous NaHCtheta3 solution and cold water, and dried under vacuum to provide 14 (5.5 g, 89% ) as a yellowish solid. MS (m/z) (Nf +H): 411, 413; 1H-NMR (400Mz, DMSO-d, ppm) 10.13 (s, IH), 9.08 (s, IH), 8.72 (s, IH), 8.01 (d, IH, J=8.55Hz), 7.94 (d, IH, J=8.97Hz), 7.47 (d, 2H, J=8.55Hz), 7.14 (d, 2H, J=8.55Hz),1.68 (s, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 115279-57-7.

Reference:
Patent; PROGENICS PHARMACEUTICALS, INC.; WO2009/155527; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 115279-57-7, A common heterocyclic compound, 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, molecular formula is C10H12N2, 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.

General procedure: To a solution of 6 (1.0 equiv) in acetic acid (2 mL/1 mmol substrate)AcONa (1.4 equiv) and substituted aniline (1.0 equiv), suchas 2 or 3-trifluoromethylaniline, were added. The resultant mixturewas stirred for 0.5 h at room temperature and quenched withwater. After the rude product was totally precipitated, it was filtered,washed with water and dissolved in DCM. The solutionwas then washed with saturated NaHCO3 solution, brine and driedover anhydrous Na2SO4. Following removal of solvent in vacuo, theresidue was purified via flash column chromatography using EA/PE(1:6) as eluent to afford corresponding ethyl 6-bromo-4-anilino-3-carboxylate quinoline derivative 7a or 7b as light yellow solid. 4.1.4.1 Ethyl 6-bromo-4-((4-(2-cyanopropan-2-yl)phenyl)amino)quinoline-3-carboxylate (7a) Light yellow solid; yield: 83%; ESI-MS: m/z = 438 [M+H]+.

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:
Article; Ma, Xiaodong; Lv, Xiaoqing; Qiu, Ni; Yang, Bo; He, Qiaojun; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 23; 24; (2015); p. 7585 – 7596;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H12N2

A mixture of 2-(4-amino-phenyl)-2-methyl-propionitrile (160 mg; 0.50 mmol), prepared as in l(B), 2-chloro-4,5-dimethoxy-benzoic acid (108 mg, 0.50 mmol), HOBt (77.0 mg; 0.50 mmol), EDC (144 mg; 0.75 mmol) and TEA (140 uL; 1.00 mmol) in dioxane (6 mL) was warmed at 100C for 2 hours. Then, the reaction was diluted with DCM and washed with IN HCl and 5% NaHCO3. The organic phase was collected, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by chromatography [SiO2, Petroleum ether/EtOAc (1/1)] to give the title compound as a white solid (30.0 mg; 17% yield).IH NMR (300 MHz, CDC13-d) delta(ppm): 8.33 (br. s., 1 H), 7.70 (m, 2 H), 7.50 (m, 2 H), 7.48 (s, 1 H), 6.91 (s, 1 H), 3.94-3.97 (m, 3 H), 3.95 (d, 3 H), 1.76 (s, 6 H).LCMS (RT): 2.24 min (Method G); MS (ES+) gave m/z: 359.18 (MH+). MP: 142-144 C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 115279-57-7.

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

Synthetic Route of 115279-57-7,Some common heterocyclic compound, 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, molecular formula is C10H12N2, 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.

Preparation I 2-Methyl-2-(4-(6-methyl-3-nitroquinolin-4-ylamino)phenyl) propanenitrile 4-Chloro-6-methyl-3-nitroquinoline (Compound of Preparation H, 660 mg, 2.97 mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (570 mg, 3.56 mmol) were dissolved in acetic acid (10 ml) and stirred for 2 hours. Water was added and the yellow precipitate was filtered off, washed with water, saturated aqueous NaHCO3 and water. The yellow solid was dried to obtain the title compound. Yield: 600 mg (58%); 1H NMR (DMSO-d6, 300 MHz): delta 9.952 (s, 1H,), 9.016 (s, 1H), 8.184 (s, 1H), 7.890-7.918 (d, 1H, J=8.4 Hz), 7.699-7.727 (d, 1H, J=8.4 Hz), 7.421-7.445 (d, 2H, J=7.2 Hz), 7.082-7.108 (d, 2H, J=7.8 Hz), 2.284 (s, 3H), 1.660 (s, 6H); MS: m/z 347 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Aminophenyl)-2-methylpropanenitrile, its application will become more common.

Reference:
Patent; Kumar, Sanjay; Vishwakarma, Ram; Mundada, Ramswaroop; Deore, Vijaykumar; Kumar, Pramod; Sharma, Somesh; US2012/108627; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 115279-57-7, 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

[00336] The synthesis of this monomer proceeds first by synthesis of the Suzuki reaction coupling partner (3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolane)quinolin-6-yl)-N-boc- methanamine starting from methyl 3-bromoquinoline-6-carboxylate. Reduction of the methyl ester with lithium aluminum hydride followed by Mitsunobu reaction with phthalimide and hydrazine cleavage provides the benzylic amine. Protection of the benzylic amine with di- tert-butyl dicarbonate followed by a Miyaura borylation reaction provides (3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolane)quinolin-6-yl)-N-boc-methanamine. (1585) [00337] An SNAr reaction of 2-(4-aminophenyl)-2-methylpropanenitrile with 6-bromo-4- chloro-3-nitroquinoline provides the substituted amino-nitro-pyridine. Reduction of the nitro group with Raney-Ni under a hydrogen atmosphere followed by cyclization with trichloromethyl chloroformate provides the aryl -substituted urea. Substitution of the free N-H of the urea with methyl iodide mediated by tetrabutyl ammonium bromide and sodium hydroxide followed by Suzuki coupling of (3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolane)quinolin-6-yl)-N-boc-methanamine and then Boc-deprotection using TFA produces the TFA salt.

The chemical industry reduces the impact on the environment during synthesis 2-(4-Aminophenyl)-2-methylpropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher; PITZEN, Jennifer; WANG, Gang; TIBREWAL, Nidhi; AGGEN, James Bradley; THOTTUMKARA, Arun P.; BURNETT, G. Leslie; GLIEDT, Micah James Evans; KISS, Gert; WON, Walter; LEE, Julie Chu-li; GILL, Adrian Liam; (538 pag.)WO2018/204416; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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. COA of Formula: C10H12N2

Example 24; l-[4-(Cyano-dimethyl-methyl)-phenyl]- 3-{4-[2-(3-Hydroxy-propylamino)- pyrimidin-4-yloxy] -phenyl} -urea188 mg (1.16 mmol) lJ’-Carbonyl-diimidazol (CDI) were given to a solution of 175 mg (1.09 mmol) 4-(cyano-dimethyl-methyl)-phenylamine (Hicks, T.A., J. Med. Chem. 22 (1979) 1460-1464) in 4.0 ml dichloro-methane and stirred for 12 h.A solution of 284 mg (1.09 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2- ylamino]-propan-l-ol in 6 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (ethyl acetate). The obtained material was left overnight with dichloromethane, the precipitate filtered, washed with ether and dried. Yield: 180 mg (37%) of the title compound. MS: 447.58 (ESI+).eta-NMR(400Hz, [DJDMSO): delta = 1.59(br, 2H, CH2-CH2-CH2), 1.67(s, 6H, CH3), 3.22(br, 2H, CH2-NH), 3.38(br, 2H, CH2-OH), 4.37(br, IH, OH), 6.05(br, IH, 5- H-pyrimidine), 7.05(br, IH, CH2NH), 7.09(d, 2H, 3-H/5-H-Ar-NH), 7.41 (d, 2H,Ar-C-CN), 7.49(m, 4H, 2-H/6-H-Ar-NH, Ar-C-CN), 8.12(d, IH, 6-H-pyrimidine), 8.75(s, IH, urea-NH), 8.79(s, IH, urea-NH).

The synthetic route of 115279-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/77548; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-(4-Aminophenyl)-2-methylpropanenitrile

1. Preparation of methyl 6-chloro-4-(4-(2-(cyanopropan-2-yl)phenylamino) -1,5-naphthyridine-3-carboxylate Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (5.0g, 18.4mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (2.96g, 18.5mmol) were dissolved in 1,4-dioxane (80mL). The reaction was conducted with stirring under reflux for 4hrs. The reaction mixture was cooled, and concentrated in a reduced pressure. The resulting solid was dissolved with dichlormethane, successively washed with saturated aqueous sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated in a reduced pressure to produce 6.54g of the title compound as a pale-yellow solid in a yield of 90.2%.

The synthetic route of 115279-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; ZHANG, Yan; EP2719697; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts