Category: nitriles-buliding-blocks

Electric Literature of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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 stirring solution of crude 8-fluoro-4-hy- drazinylquinoline (0.27 g, 1.5 mmol) and 3-oxo-butyroni- trile (0.15 g, 0.19 mmol) in pyridine (3 mE) was heated at 80 C. for 15 h. After cooling to room temperature, aqueous saturated sodium bicarbonate was added to the reaction mixture and extracted with dichioromethane (3x 10 mE). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was used directly without thrther purification (0.14 g, 0.76 mmol, 50%)

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

Reference:
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (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. 628-20-6, name is 4-Chlorobutyronitrile, A new synthetic method of this compound is introduced below., SDS of cas: 628-20-6

To a solution of 2-bromo-4-nitrophenol (100 g, 0.46 mol) and potassium carbonate (190 g, 1.37 mol) in DMF (1.20 L) was added 4-chlorobutanenitrile (52.1 mL, 550 mmol) and heated at 65 C for 2 h. Ice water was added and the mixture was extracted with ethyl acetate. The organic layer was separated and washed with water and brine, dried over anhydrous sodium sulphate, concentrated and purified by columnchromatography (silica gel, 1:1 ethyl acetate in petroleum ether) to obtain the title compound. Yield: 101 g (77 %); 1H NMR (300 MHz, DMSO-d6): O 2.06-2.17 (m, 2H, -CH2), 2.69 (t, J = 6.0 Hz, 2H, CH2), 4.28 (t, J = 6.0 Hz, 2H, -OCH2), 7.35 (d, J = 9.3 Hz, 1H, Ar), 8.26 (dd, J = 2.7 Hz, 9.3 Hz, 1 H, Ar), 8.43 (d, J = 2.7 Hz, 1 H, Ar); MS: mlz 285.0 (M).

The synthetic route of 628-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; KULKARNI, Sarang; KULKARNI, Mahesh; MUKHERJEE, Sumit; YADAV, Rajesh, Kumar; AGARWAL, Madhavi; BURUDKAR, Sandeep; SATHE, Santosh; WO2015/49629; (2015); 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. 4426-11-3, name is Cyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Cyclobutanecarbonitrile

Example 234A 1-(6-(trifluoromethyl)pyridin-2-yl)cyclobutanecarbonitrile Cyclobutanecarbonitrile (1.474 g, 18.17 mmol) and 2-fluoro-6-(trifluoromethyl)pyridine (2.0 g, 12.11 mmol) were dissolved in toluene (30 mL). 0.5M potassium hexamethyl disilazide (36.3 mL, 18.17 mmol) in toluene was added, the solution turned dark, and the reaction was exothermic. The brown solution was stirred overnight at ambient temperature. The reaction was quenched with saturated NH4Cl solution and diluted with EtOAc. The organic layer was washed with saturated NH4Cl solution, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica (5-50% EtOAc in heptane) to give Example 234A (1.188 g, 5.25 mmol, 43.4% yield) as a yellow liquid. MS (DCI+): m/z 244 (M+NH4). 1H NMR (300 MHz, DMSO-d6) delta 8.21 (t, J=8.0 Hz, 1H), 7.95 (d, J=4.7 Hz, 1H), 7.92 (d, J=4.5 Hz, 1H), 2.86-2.69 (m, 4H), 2.38-2.19 (m, 1H), 2.15-1.96 (m, 1H).

The synthetic route of 4426-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
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3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, 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. Recommanded Product: 3215-64-3

EXAMPLE 1 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture is heated at reflux for 4 hours, cooled, and the insoluble product washed with diethylether to give 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine, mp 325-332 C. (MS).

The synthetic route of 3215-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blankley; Clifton John; Doherty; Annette Marian; Hamby; James Marino; Panek; Robert Lee; Schroeder; Mel Conrad; Showalter; Howard Daniel Hollis; Connolly; Cleo; US5733913; (1998); A;,
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Reference of 5866-98-8, These common heterocyclic compound, 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, 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.

Example 30 Preparation of 6-Chloro-5-cyano-7-nitro-1,4-dihydroquinoxaline-2,3-dione To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (3.935 g, 18.13 mmol, Lancaster, used as received) in DMF (25 mL) at 70 C., an aqueous solution of sodium glycinate (1.760 g, 18.13 mmol, Aldrich, used as received) in water (25.0 mL) was added dropwise. The resulting solution was stirred at 70 C. for 48 h. The suspension was cooled to room temperature and the precipitated yellow solid was filtered, washed with chloroform (20 mL), and dried under vacuum to furnish 2.020 g (44%) of pure (1 H NMR) N-(3′-chloro-2′-cyano-6′-nitro)phenylglycine as a yellow powder. 1 H NMR (DMSO-d6): delta3.888 (d, 2H, J=3.9 Hz), 6.857 (d, 1H, J=9.0 Hz).

Statistics shows that 2,6-Dichloro-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 5866-98-8.

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
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Synthetic Route of 4592-94-3, 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 4592-94-3 as follows.

General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kelada, Mark; Walsh, John M. D.; Devine, Robert W.; McArdle, Patrick; Stephens, John C.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 122 – 1228;,
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Application of 622-75-3, A common heterocyclic compound, 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, molecular formula is C10H8N2, 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.

Scheme I, step A: Into a 250 ML single neck flask was placed sodium hydride 60% (5.4 g, 134.5 mmol) in DMF (100 ML) at -15 C. 1,4-Phenyldiacetonitrile (5 g, 32 mmol) was added to the solution slowly and the mixture was stirred for 1/2 hour.The reaction mixture was treated with methyl iodide (8.4 ML, 134.5 mmol).The mixture was warmed up to RT while stirring for 12 hours.The reaction mixture was poured into ice water (600 ML) until product was precipitated out.The precipitate was filtered off and washed with cold water to provide the intermediate title compound, 2-[4-(1-cyano-isopropyl)phenyl]-2-methylpropanenitrile, (6.8 g, 100%) as a white solid.Electron spray M.S. 230 (M*+H2O).

The synthetic route of 622-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Knobelsdorf, James Allen; Shepherd, Timothy Alan; Tromiczak, Eric George; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/229102; (2003); A1;,
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Reference of 1735-88-2, 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. 1735-88-2, name is 2-Cyano-N-(4-fluorophenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: Preparation of 2-cyano-N-(4-fluorophenyl)-3-[5-(2,5,8-trioxa-nonyl-1-yl)furan-2-yl]-2-acrylamide (JK-06A) 2-cyano-N-(4-fluorophenyl)acetamide (4.0 g, 22.4 mmol), 5-(2,5,8-trioxa-nonyl-1-yl)furan-2-carbaldehyde (3.4 g, 14.9 mmol) and 1-methylpiperazine (2.2 g, 22.4 mmol) were dissolved in CH3OH (50 mL), stirred at room temperature overnight. The solid was collected by filtration, washed with CH3OH (50 mL) to give 1.6 g of a yellow solid with a yield of 27.6%. MS Detection: MASS(ESI+) m/z=411.3 (M+Na)+.

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

Reference:
Patent; JENKEM TECHNOLOGY CO., LTD. (BEIJING); FENG, ZEWANG; JIA, JIANHUAN; LIU, YAN; WANG, ZHENGUO; ZHAO, XUAN; (13 pag.)US2016/272604; (2016); A1;,
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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 1080-74-6 as follows. category: nitriles-buliding-blocks

To a degassed solution of intermediate 16 (75 mg, 0.06 mmol) and 3- (dicyanomethylidene)indan-l -one (87 mg, 0.45 mmol) in chloroform (1 .9 cm3) is added pyridine (0.36 cm3, 4.46 mmol) and the reaction mixture stirred at 23 C for 18 hours. Methanol (40 cm3) is added and the resulting suspension filtered and washed with methanol (3 x 10 cm3). The resulting solid is purified by column chromatography eluting with a graded solvent system (40-60 petrol:dichloromethane; 1 :1 to 2:3) to give compound 83 (63 mg, 65%) as a blue solid. 1H NMR (400 MHz CD2CI2) 8.75 (2H, s), 8.60 (2H, dd, J 7.1 , 1 1 .4), 7.84 (2H, dd, J 6.9, 1 .8), 7.63 – 7.80 (8H, m), 7.44 (2H, d, J 8.4), 7.39 (2H, d, J 4.2), 7.08 – 7.15 (8H, m), 7.04 (4H, d, J 7.6), 6.96 (4H, m), 2.49 (8H, t, J 7.6), 1 .49 (8H, t, J 4.2), 1 .09 – 1 .26 (24H, m), 0.68 – 0.76 (12H, m).

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
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Synthetic Route of 72115-09-4, The chemical industry reduces the impact on the environment during synthesis 72115-09-4, name is 5-Amino-2-bromobenzonitrile, I believe this compound will play a more active role in future production and life.

Step-1 : Synthesis of tert-butyl (4-bromo-3-cvanophenyl)carbamate. Di-tert-butyl dicarbonate (1.14g, 4.8mmol) was added to a solution of 5-amino-2- bromobenzonitrile (0.8g, 4mmol) and DMAP (0.58g, 4.8mmol) in DCM (20mL) and the resulting reaction mixture was stirred for 8h at room temperature. After completion of reaction, the reaction mixture was diluted with ice cold water and extracted with DCM (3×50 mL). The combined organic phase was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by 100-200 mesh silica column by eluting with 15% ethyl acetate -hexane to afford the title compound (lg, 83%). LCMS: m/z = 297.15 (M+H)+.

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, 5-Amino-2-bromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; PODDUTOORI, Ramulu; MUKHERJEE, Subhendu; GOSWAMI, Rajeev; (174 pag.)WO2016/142855; (2016); A2;,
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