Month: July 2021

Reference of 218632-01-0,Some common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58). Sodium hydride (88 mg, 95%) was added, under argon flush, to a solution of tert-butyl 9-(2,6-difluorobenzyl)-2-amino-8-oxo-8,9-dihydropurine-7-carboxylate (57) (191 mg) and 3-fluoro-4-nitrobenzonitrile (415 mg) in DMF (5 mL) at -40 C. The reaction mixture was allowed to warm to -20 C. over 3 hr then quenched by the addition of sat. aq. NH4Cl, once at RT the mixture was diluted with EtOAc and separated. The organics were washed with brine (3*), dried, filtered and evaporated, purified via column chromatography, (eluted with DCM and 1 and 2.5% MeOH/DCM) to yield tert-Butyl 9-(2,6-difluorobenzyl)-2-(5-cyano-2-nitrophenylamino)-8-oxo-8,9-dihydropurine-7-carboxylate (58) (288 mg), MH+=524. tert-Butyl 9-(2,6-difluorobenzyl)-2-(6-cyano-1H-benzo[d]imidazol-1-yl)-8-oxo-8,9-dihydropurine-7-carboxylate (60).

The synthetic route of 218632-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA DRUG DISCOVERY, INC.; US2008/119496; (2008); A1;,
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Electric Literature of 4426-11-3, 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 4426-11-3 as follows.

Example 44B l-(l-(3-chlorophenyl)ethyl)cyclobutanecarbonitrile n-BuLi (4.7 mL, 11.8 mmol, 2.5 M in hexane) was added to a solution ofdiisopropylamine (1.13 g, 11.2 mmol) in THF (20 mL) at -78C. After stirring for 5 min, neat cyclobutancarbonitrile (0.8 g, 9.87 mmol) was added and the mixture was stirred at -78C for 1 hour. Then a solution of Example 44A (2.6 g, 11.8 mmol) in THF (10 mL) was added and the mixture was stirred at -78C for 1 h. The mixture was quenched with water and extracted with EtOAc (40 mL). The solvent was evaporated and the residue was used directly in the next step without further purification. LC-MS: m/z 220 (M+H).

According to the analysis of related databases, 4426-11-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD; BAYBURT, Erol, K.; CLAPHAM, Bruce; COX, Phil, B.; DAANEN, Jerome, F.; GOMTSYAN, Arthur; KORT, Michael, E.; KYM, Philip, R.; VOIGHT, Eric, A.; WO2012/19315; (2012); A1;,
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Electric Literature of 1897-52-5, These common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, 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 3 : 2-Fluoro-6- [1 -(2-fluorophenyl)piperidin-4- ylmethoxy]benzonitrile-(Method C).To a cold (ice water) suspension of sodium hydride (0.044 g, 1.1 mmol) in anhydrous DMF (1 mL) is added a solution of l-(2-fluorophenyl)piperidin-4-yl]methanol (0.19 g, 0.91 mmol) in anhydrous DMF (2 mL) over 11 minutes. After allowing to room temperature over 2 hours, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (0.14 g, 1.0 mmol) in anhydrous DMF (1 mL), and allowed to room temperature over 18 hours. The reaction mixture is poured into ice water with vigorous stirring and the resulting solid is filtered, washed with water, and dried under vacuum 1.5 hours to give 2-luoro-6-[l-(2-fluorophenyl)piperidin-4-yloxy]benzonitrile (0.19O g, 63% yield).

The synthetic route of 1897-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; deCODE Chemistry, Inc.; WO2008/16973; (2008); A1;,
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Related Products of 34403-48-0, A common heterocyclic compound, 34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, molecular formula is C9H10N2, 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.

A round-bottom flask was charged with norbornane-2-carboxylic acid (1.0 g, 1 eq.) and thionyl chloride (O.95 g, 2 eq.) was added dropwise. The mixture was warmed to 70 C. for 1 hour. The mixture was cooled to room temperature and dichloromethane (20 mL) was added. Subsequently 4-(methylaminomethyl)benzonitrile (1.03 g, 1.1 eq) was added portion wise. The mixture was stirred at room temperature over night until HPLC indicated complete conversion. The organic layers were washed with hydrochloric acid (1 M), brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the title compound was used directly without further purification.

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; TERTERYAN-SEISER, Violeta; GRAMMENOS, Wassilios; QUINTERO PALOMAR, Maria Angelica; CRAIG, Ian Robert; WIEBE, Christine; MENTZEL, Tobias; FEHR, Marcus; ESCRIBANO CUESTA, Ana; WINTER, Christian Harald; LOHMANN, Jan Klaas; MUELLER, Bernd; CAMBEIS, Erica; GROTE, Thomas; SEET, Michael; (36 pag.)US2020/45974; (2020); 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. 64248-62-0, name is 3,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3F2N

Potassium carbonate (19.9 g, 144 mmol) was added to a mixture of 3,4-difluorobenzonitrile (10.0 g, 71.9 mmol) and 4-hydroxybenzaldehyde (8.78 g, 71.9 mmol) in N,N-dimethylformamide (200 mL). The reaction mixture was heated to 100 C. for 4 hours, whereupon it was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was washed with water (3×200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo, affording the product as a yellow solid (17.7 g). By 1H NMR, this material contained some N,N-dimethylformamide. Yield, corrected for N,N-dimethylformamide: 16.8 g, 69.6 mmol, 97%. 1H NMR (400 MHz, CDCl3) delta 9.99 (s, 1H), 7.93 (br d, J=8.6 Hz, 2H), 7.58-7.48 (m, 2H), 7.21 (dd, J=8.4, 8.0 Hz, 1H), 7.14 (br d, J=8.6 Hz, 2H).

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 64248-62-0.

Reference:
Patent; Pfizer Inc.; Kablaoui, Natasha Mariam; Green, Michael Eric; Montgomery, Justin Ian; Brodney, Michael Aaron; Verhoest, Patrick Robert; Kauffman, Gregory Wayne; Rankic, Danica Antonia; Mente, Scot Richard; Rogers, Bruce Nelsen; Arora, Kapildev Kashmirilal; Dunn, Matthew Francis; (98 pag.)US2018/148432; (2018); 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. 2042-37-7, name is 2-Bromobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H4BrN

General procedure: activityThe catalytic activities of the prepared catalysts were testedfor the Suzuki-Miyuara cross-coupling reaction of phenylboronicacid with various bromoarenes. In a typical experiment, 0.70 mmolof the aryl bromide, 1.5 molar equivalents of phenylboronic acidand 1.5 molar equivalents of base, respectively, and 1.3 mmol ofanisole (internal standard) were dissolved in 20 ml of solvent. 5 mgof the catalyst (corresponding to approximately 0.05 mol% palla-dium) were added. The reaction was carried out under stirring at 75C. To monitor the reaction progress, samples from the reac-tion solution (100 l) were taken after 15, 30, 60, 90 and 120 min.HPLC sample solutions were prepared by dissolving 100 l of thereaction solution in 1 ml of the initial mobile phase. HPLC analy-sis was done using an Agilent 1100 series HPLC system (Agilent,Waldbronn, Germany), equipped with an online degasser, qua-ternary pump, autosampler, thermostatted column compartmentand UV-vis diode array detector. An Agilent Poroshell 120 EC-C18 reversed-phase column (50 × 4.6 mm; 2.7 m) was used asstationary phase. Analysis was carried out under gradient elu-tion conditions using a mobile phase consisting of methanol andaqueous phosphoric acid (water: phosphoric acid = 300:1 v/v). Col-umn temperature was set to 25C. UV-detection was performed atwavelengths of 237 and 270 nm over a run time of 15 min.

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lichtenegger; Maier; Hackl; Khinast; Goessler; Griesser; Kumar, V.S. Phani; Gruber-Woelfler; Deshpande; Journal of Molecular Catalysis A: Chemical; vol. 426; (2017); p. 39 – 51;,
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Electric Literature of 154607-01-9, 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. 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Bromo-2-chloro-cyanobenzne (2.Og, 9.3 mmol) and sodium perborate (4.3g, 28 mmol) were dissolved in dioxane (40ml), water (40ml) and heated at reflux for 1 hour. An extra 2.0 g of perborate was added and the reaction was refluxed for 1 hour. The reaction was cooled, extracted with DCM (2 x 100 ml), dried and the solvent was removed in vacuo to yield a white solid. Ether was added to dissolve any remaining starting material and the solid was stirred for 10 minutes and filtered (1.35g, 62%). NMR (299.954 MHz, CDCl3) 12.61 (s, IH), 12.50 (s, IH), 12.38 – 12.31 (m, 2H), 12.13 (d, IH).

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, 4-Bromo-2-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/64251; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 127667-01-0, name is 2-Fluoro-5-methoxybenzonitrile, 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 127667-01-0, name: 2-Fluoro-5-methoxybenzonitrile

11 g of 2-fluoro-5-methoxybenzonitrile was added to a mixed solvent of 200 ml of methanol and 100 ml of water, and 9 g of hydroxylamine hydrochloride and 12 g of anhydrous sodium acetate were added. The reaction was heated under reflux for 12 hours, and water and ethyl acetate were added thereto. The solution was separated by extraction, and the organic layer was collected, dried and concentrated. The residue was separated on a silica gel column to obtain 9 g of 2-fluoro-N’-hydroxy-5-methoxybenzylhydrazone.

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-Fluoro-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Bu Gonggaofamingren; (6 pag.)CN107698535; (2018); A;,
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Application of 77668-42-9, A common heterocyclic compound, 77668-42-9, name is 2,3-Dichlorobenzoyl cyanide, molecular formula is C8H3Cl2NO, 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.

400 g (2 moles) of 2,3-dichlorobenzoyl cyanide are added to a mixture prepared from 333.6 g (2.45 moles) of aminoguanidine bicarbonate in 800 mL of methanesulphonic acid. The mixture is then heated at 45C for 5 hours, cooled to 10C and 2.4 L of water is added slowly, controlling exothermy at 20-30C. The mixture is then adjusted to pH 11 with a 50% NAOH solution, filtered, the solid washed with water and dried at 45C to yield 419.8 g (82%) of the product of the title. NMR 1H (DMSO), delta (ppm): 6. 5- 6. 9 (s, 4H,-N=C (NH2) 2), 7.4 (t, 1H, ARH), 7. 6 (d, 2H, ArH). M. p. = 180-183C.

The synthetic route of 77668-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS VITA, S.A.; WO2004/39767; (2004); A1;,
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Synthetic Route of 501-00-8,Some common heterocyclic compound, 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, molecular formula is C8H6FN, 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.

Example 1 : Preparation of methyl 3-(3-bromo-5-fluorophenyl)-4-cyano-4-(3-fluoro- phenyl)butyrate [1-316]; At -78C and under argon, 248 mg of (3-fluorophenyl)acetonitrile were added dropwise to a solution of 238 mg of potassium tert-butoxide in 2 ml of THF, and a solution of 500 mg of methyl 3-(3-bromo-5-fluorophenyl)acrylate in 1 ml of THF was then added. After 1 h of stirring at -78C, 5 ml of CH2CI2 were added. After washing with 2N HCI, sat. NaHCO-3 solution and sat. NaCI solution, drying of the organic phase and removal of the solvent under reduced pressure, the residue was purified by preparative HPLC.This gave 215 mg of the title compound (erythro:threo ratio 1.9:1 ).

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-Fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; BASF SE; VESCOVI, Andrea; REINHARD, Robert; SIEVERNICH, Bernd; ZAGAR, Cyrill; KIBLER, Elmar; NIGGEWEG, Ricarda; KUeHN, Toralf; WITSCHEL, Matthias; MOBERG, William Karl; PARRA RAPADO, Liliana; QU, Tao; STELZER, Frank; KLOET, Andree van der; SEITZ, Thomas; EHRHARDT, Thomas; KREUZ, Klaus; GROssMANN, Klaus; MICHROWSKA-PIANOWSKA, Anna Aleksandra; SIMON, Anja; EVANS, Richard Roger; HUPE, Eike; REINHARD, Klaus; BERGTOLD, Matthias; KOLLE, Susanne Noreen Evelyn; TRESCH, Stefan; SONG, Dschun; MAJOR, Julia; HUTZLER, Johannes; NEWTON, Trevor William; WO2011/98417; (2011); A1;,
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