Category: 658-99-1

Wu, Hai-Qiu; Yan, Zi-Hong; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe published the artcile< Towards new C6-rigid S-DABO HIV-1 reverse transcriptase inhibitors: Synthesis, biological investigation and molecular modeling studies>, Formula: C8H5F2N, the main research area is C6 rigid SDABO analog preparation HIV1 RT inhibitor; HIV-1 reverse transcriptase; NNRTIs; Rigid conformation; S-DABO; SAR.

A series of C6-rigid S-DABO analogs characterized by a substituted benzoyl group at C6 position of the pyrimidine ring has been synthesized and biol. evaluation as NNRTIs against wild-type HIV-1 strain IIIB, double RT mutant (K103N + Y181C) strain RES056 as well as HIV-2 strain ROD in MT-4 cell cultures. Most of the compounds exhibited moderate antiviral activities. Among them, compound 7q displayed the highest anti-HIV-1 activity with an EC50 value of 0.26 μM and a selectivity index (SI) of 541. The preliminary structure-activity relationship (SAR) of these new S-DABOs was investigated, the target RT was confirmed and docking study was performed.

Bioorganic & Medicinal Chemistry published new progress about Antiviral agents. 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Formula: C8H5F2N.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ali, Abdelselam; Bliese, Marianne; Rasmussen, Jo-Anne M.; Sargent, Roger M.; Saubern, Simon; Sawutz, David G.; Wilkie, John S.; Winkler, David A.; Winzenberg, Kevin N.; Woodgate, Ruth C. J. published the artcile< Discovery of (Z)-2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives active against Haemonchus contortus and Ctenocephalides felis (cat flea)>, Synthetic Route of 658-99-1, the main research area is phenylpyrrolyl acrylonitrile derivative preparation antiparasitic activity.

A series of 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives, e.g., I, were synthesized and evaluated for in vitro activity against the endoparasite Haemonchus contortus and the ectoparasite Ctenocephalides felis. Some compounds had significant in vitro activity against these parasites.

Bioorganic & Medicinal Chemistry Letters published new progress about Parasitic infection. 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Synthetic Route of 658-99-1.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yoshida, Yu; Naoe, Yoshimitsu; Terauchi, Taro; Ozaki, Fumihiro; Doko, Takashi; Takemura, Ayumi; Tanaka, Toshiaki; Sorimachi, Keiichi; Beuckmann, Carsten T.; Suzuki, Michiyuki; Ueno, Takashi; Ozaki, Shunsuke; Yonaga, Masahiro published the artcile< Discovery of (1R,2S)-2-{[(2,4-Dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006): A Potent and Efficacious Oral Orexin Receptor Antagonist>, Name: 2-(3,4-Difluorophenyl)acetonitrile, the main research area is E2006 oral orexin receptor antagonist discovery SAR sleep disorder.

The orexin/hypocretin receptors are a family of G protein-coupled receptors and consist of orexin-1 (OX1) and orexin-2 (OX2) receptor subtypes. Orexin receptors are expressed throughout the central nervous system and are involved in the regulation of the sleep/wake cycle. Because modulation of these receptors constitutes a promising target for novel treatments of disorders associated with the control of sleep and wakefulness, such as insomnia, the development of orexin receptor antagonists has emerged as an important focus in drug discovery research. Here, we report the design, synthesis, characterization, and structure-activity relationships (SARs) of novel orexin receptor antagonists. Various modifications made to the core structure of a previously developed compound (-)-5 (I), the lead mol., resulted in compounds with improved chem. and pharmacol. profiles. The investigation afforded a potential therapeutic agent, (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006, II), an orally active, potent orexin antagonist. The efficacy was demonstrated in mice in an in vivo study by using sleep parameter measurements.

Journal of Medicinal Chemistry published new progress about Brain (brain penetrability). 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Name: 2-(3,4-Difluorophenyl)acetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Xiuxiu; You, Cai; Yang, Yusheng; Yang, Yuhong; Li, Pan; Gu, Guoxian; Chung, Lung Wa; Lv, Hui; Zhang, Xumu published the artcile< Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position>, COA of Formula: C8H5F2N, the main research area is Pregabalin Phenibut Baclofen enantioselective preparation; beta cyano ester enantioselective preparation; cyanocinnamic ester beta asym hydrogenation rhodium catalyst.

With the assistance of hydrogen bonds, the first Rh-catalyzed asym. hydrogenation of β-cyanocinnamic esters R1CNC=CHCO2R2 [R1 = C6H5, 2-FC6H4, 2-naphthyl, etc.; stereo = Z or E] is developed, affording chiral β-cyano esters R1CNCHCHCO2R2 with excellent enantioselectivities (up to 99% ee). This novel methodol. provides an efficient and concise synthetic route to chiral GABA-derivatives such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with a single H-bond donor performs better than that with double H-bond donors, which is a novel discovery in the metal organocatalysis area.

Chemical Science published new progress about Aromatic nitriles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (β-cyano esters). 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, COA of Formula: C8H5F2N.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, 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 658-99-1, category: nitriles-buliding-blocks

Example A2 erythro- and threo-methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate (Table 2, Examples erythro-Ibb748 and threo-Ibb748) Under protective gas (Ar), 5 ml of N,N-dimethylformamide and 0.067 g (1.244 mmol) of potassium tert-butoxide were added to 1.127 g (6.219 mmol) of methyl 3-(5-fluoropyridin-3-yl)acrylate and 1.000 g (6.530 mmol) of (3,4-difluorophenyl)acetonitrile in 15.0 ml of toluene, and the mixture was stirred at 70 C. for 5 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane. The mixture was washed successively with water, 0.1 N aqueous hydrochloric acid and saturated aqueous sodium chloride solution and the organic phase was dried over sodium sulphate. Removal of the solvent under reduced pressure and chromatography of the residue on silica gel gave 1.008 g (46% of theory) of a mixture of erythro- and threo-methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate (erythro-Ibb748:threo-Ibb748=60:40). The configuration was assigned by comparison of the chemical shifts of the respective CHCN doublets at 4.12 ppm and 4.48 ppm, respectively, in the 1H-NMR (CDCl3).

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, 2-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AG; JAKOBI, Harald; MOSRIN, Marc; DIETRICH, Hansjoerg; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; (66 pag.)US2015/327546; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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 stirring solution of substituted benzonitrile/phenylacetonitrile (1mmol) in anhydrous methanol (20mL) under N2 atmosphere was added hydroxylamine hydrochloride (1.2mmol). Triethylamine (2.5mmol) was added under continuous stirring condition and the mixture was then heated under reflux condition for overnight at 60C and continued until complete consumption of the starting material (monitored by TLC) [22,23]. The excess solvent was then removed under reduced pressure and the obtained residue was washed successively with water and brine, and extracted with ethylacetate (3×10mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. This reaction mixture was purified using silica gel column chromatography with a gradient solvent system of 10-20% ethylacetate to hexane to obtain the desired product with an average yield of 70-80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Article; Paul, Saurav; Roy, Ashalata; Deka, Suman Jyoti; Panda, Subhankar; Trivedi, Vishal; Manna, Debasis; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 364 – 375;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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 1: Methyl 4-cyano-4-(3,4-difluorophenyl)-3-(3-fluorophenyl)butanoate Under protective gas (Ar), 3.828 g (25.0 mmol) of (3,4-difluorophenyl)acetonitrile and 0.281 mg of potassium tert-butoxide were added to 4.099 g (22.7 mmol) of methyl 3-(3-fluorophenyl)acrylate in 25.0 ml of toluene, and the mixture was stirred in a closed vessel at 65 C. for 5 h. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 7.3 g (87% of theory) of the diastereomeric methyl 4-cyano-4-(3,4-difluorophenyl)-3-(3-fluorophenyl)butanoate (erythro:threo=65:35 according to integration of the methyl singlets in the 1H-NMR in CDCl3 at 3.68 and 3.59 ppm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Mosrin, Marc; Jakobi, Harald; Angermann, Alfred; Gatzweiler, Elmar; Haeuser-Hahn, Isolde; Heinemann, Ines; Rosinger, Christopher Hugh; Lehr, Stefan; Schnatterer, Stefan; US2014/235446; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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.

22.1.1 Synthesis of 3-cyano-3-(3,4-difluorophenyl)pentanedioic Acid Diethyl Ester Prepare by the method of Example 3.1.2 using 3,4-difluorophenylacetonitrile to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; Maynard, George D.; Le, Tieu-Binh; US2001/34343; (2001); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 10 4-Cyano-4-(3,4-difluorophenyl)-5-(1,3-dioxolan-2-yl)pentanoic acid A solution of 3,4-difluorobenzyl cyanide (20g, 0.13mol) in tetrahydrofuran (20ml) was added dropwise to a solution of lithium bis(trimethylsilyl)amide (1.0M, 144ml, 0,14mol) in tetrahydrofuran at 0C under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours, after which time it was cooled to 0C and a solution of 2-bromomethyl-1,3-dioxolane (15ml, 0.14mol) in tetrahydrofuran (15ml) was added followed by tetra-n-butylammonium iodide (2g, 5.4mmol). The reaction mixture was warmed to room temperature and stirred for 18 hours. A further portion of solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 144ml, 0.14mol) was added dropwise to the reaction mixture at 0C and then the mixture was allowed to warm to room temperature over 5 hours. The reaction mixture was cooled to 0C and a solution of ethyl 3-bromopropionate (18ml, 0.14mol) in tetrahydrofuran (20ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. A solution of sodium hydroxide (7.8g, 0.20mol) in water (50ml) was added to the crude reaction mixture at 0C and the mixture then allowed to warm to room temperature. The reaction mixture was stirred for 36 hours. The reaction mixture was partitioned between water and diethyl ether, the organic layer re-extracted with water and the combined aqueous layers were acidified to pH 1.0 with aqueous hydrochloric acid (2N). The aqueous layer was extracted with ethyl acetate (x2), dried over Na2SO4and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluding with a gradient system of dichloromethane gradually changing to dichloromethane: methanol: acetic acid (95: 5: 1, by volume) to afford the title compound as a brown oil (15.0g, 37%) which solidified on standing. 1H-NMR (CDCl3): delta = 7.30 (1H, m), 7.20 (2H, m), 4.80 (1H, m), 3.95 (2H, m), 3.80 (2H, m), 2.50 (2H, m), 2.30 (2H, m), 2.20 (2H, m). m/z: 312 (MH+).

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, 2-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; Pfizer Limited; EP992493; (2000); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, 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 658-99-1, Application In Synthesis of 2-(3,4-Difluorophenyl)acetonitrile

Example A2 erythro- and threo-methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate (Table 2, Examples erythro-Ibb748 and threo-Ibb748) Under protective gas (Ar), 5 ml of N,N-dimethylformamide and 0.067 g (1.244 mmol) of potassium tert-butoxide were added to 1.127 g (6.219 mmol) of methyl 3-(5-fluoropyridin-3-yl)acrylate and 1.000 g (6.530 mmol) of (3,4-difluorophenyl)acetonitrile in 15.0 ml of toluene, and the mixture was stirred at 70 C. for 5 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane. The mixture was washed successively with water, 0.1 N aqueous hydrochloric acid and saturated aqueous sodium chloride solution and the organic phase was dried over sodium sulphate. Removal of the solvent under reduced pressure and chromatography of the residue on silica gel gave 1.008 g (46% of theory) of a mixture of erythro- and threo-methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate (erythro-Ibb748:threo-Ibb748=60:40). The configuration was assigned by comparison of the chemical shifts of the respective CHCN doublets at 4.12 ppm and 4.48 ppm, respectively, in the 1H-NMR (CDCl3).

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, 2-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AG; JAKOBI, Harald; MOSRIN, Marc; DIETRICH, Hansjoerg; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; (66 pag.)US2015/327546; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts