Month: July 2021

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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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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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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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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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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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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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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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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Related Products of 5653-62-3, The chemical industry reduces the impact on the environment during synthesis 5653-62-3, name is 2,3-Dimethoxybenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of 2, 3-dihydroxy benzoic acid form 2, 3-dimethoxy benzoic acid To a stirred solution of 2, 3-dimethoxy benzoic acid (lOOg; 0.549 mol) in dichloromethane (500 mL) and catalytic amount of DMF (~2 mL) at a temperature about 30-35C, thionyl chloride (130.6g ; 1.102 mol) was added and stirred for a period of two hours. Reaction was monitored by TLC for completion of the starting material (NMT- 5%).If reaction not completed added thionyl chloride (9.8 g; 0.823 mol). Upon completion of reaction, the reaction mass was quenched in to the -5C chilled aqueous ammonia (580 mL) solution at a temperature below 15C under stirring. The reaction mass was stirred at temperature 30-35C over a period of 30 min. The separated organic fraction was concentrated under atmospheric distillation at below 50C, charged toluene (100 ml) and co-distilled until the reaction mass moisture content become less than 0.5 %. The obtained benzamide compound was dissolved in toluene (500 mL) at temperature about 30-35C.To the reaction mass was added POCl3 (126.3 g; 0.824 mol).The temperature of the reaction mass was raised to 80-85C and maintained over a period of 1 -2 hours for the completion of the reaction (Progress of the reaction was monitored by HPLC until the benzamide NMT 1.0 %). If the reaction was not completed, added second lot of POCl3 (lO.lg; 0.06 mol) at 30-35C. The reaction mass was cooled to a temperature about 30-35C upon completion of the reaction. The reaction mixture was added to cold water (1000 mL) at 0-5C.The organic fraction was separated and washed with 8% sodium bicarbonate solution. The organic fraction was separated and azeotropic distilled at 110-115C (until moisture content NMT 0.2 %), after reaching moisture content to normal limit cooled the reaction mass temperature to 40C and distilled reaction mass volume becomes ~3 volumes under vacuum at a temperature 40-50C.After distillation cooled the reaction mass temperature to 30-35C. In another RB flask charged toluene (160 ml), triethyl amine (199.7 g; 1.977 mol) at 30-35C and stirred for 10 min. charged aluminum chloride (52.7 g 5; 1.977 mol) in five lots with the gap of 10 min between each lot addition (addition of aluminum chloride may raise the temperature to 45-50C). The reaction mass temperature was raised to about 70-75 C and added above reaction mass (methoxy compound) for 30 min. maintained the reaction mass at 70-75C for 8 hr. Progress of the reaction was monitored by HPLC (until the 2,3-dimethoxybenzonitrile content 0.25 % and 3-methoxy-2-hydroxybenzonitrile content 0.2 %). If reaction was not completed added second lot of triethyl amine (27.7 g; 0.27 mol) and aluminum chloride (36.6 g; 0.27 mol).Upon completion of the reaction, the reaction mixture was cooled to 30-35C and quenched with chilled aqueous HC1 (prepared by addition of water (500 ml) and Cone. HC1 (500 ml)) at 15C. Stirred reaction mass at 25-30C for about 30 min, filtered the obtained solids and separated aqueous and organic layers. Charged MIBK (320 ml) to the solids and charged above aqueous layer, filtered through celite and separated aqueous and organic layers. To the aqueous layer given MIBK (320+160 ml) extractions. To the combined organic layer given 20% sodium chloride solution washing, organic layer was azeotropic distilled at 110C to remove the water (moisture content NMT 0.2 %).Cooled the reaction mass temperature to 30C and filtered through 0.45 micron / 1 micron filter. To the filterate charged 1% EDTA (400 ml), stirred for 30 min and filtered through 10 micron cloth. The organic fraction was separated and distilled off to obtain the residue. The residue was treated with dichloromethane (400 ml) and the solid obtained was filtered and dried under vacuum over 6 hr at 60-65C to obtain the title compound 2, 3-dihydroxy benzonitrile. (56g, yield 75.4%) Purity by HPLC 99.81 %; Impurity A: 0.05% Impurity B: 0.07 %

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-Dimethoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; MUDDULURU, Hari Krishna; MADHAVARAM, Shankar; WO2014/13512; (2014); A1;,
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Synthetic Route of 34667-88-4, 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. 34667-88-4 name is 2-Fluoro-4-nitrobenzonitrile, 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.

Example 69; Synthesis of 2-(pyridin-2-ylamino)-lH-benzimidazole-5-carboxylic acid (3 -amino- IH- indazol-6-yl)-amideTo a solution of 2-fluoro-4-nitrobenzonitrile (10 mmol) in isopropanol (30 mL) was added aqueous hydrazine (4 mL). The resulting solution was heated at 800C for 12 h. The reaction mixture was then concentrated, water (30 mL) was added, and the solution was extracted with ethyl acetate (2×25 mL). The combined organics were washed with water (30 mL) and brine (30 mL) and dried over anhydrous sodium sulfate. The volatiles were removed in vacuo yielding 3-amino-6-nitroindazole as an orange solid, which was utilized for further transformation without further purification.The nitro compound from above was hydrogenated, following general procedure F, to yield 3,6-diaminoindazole.2-Isothiocyanatopyridine (4 mmol), prepared from 2-aminopyridine employing general procedure A, was reacted with methyl 3,4-diaminobenzoate as described in general procedure B to afford 2-(pyridin-2-ylamino)-lH-benzirnidazole-S-carboxylic acid methyl ester. This ester was hydrolyzed, following general procedure C, to obtain 2-(pyridin-2- ylamino)-lH-benzimidazole-5-carboxylic acid.The cafboxylic acid (0.5 mmol) from above was coupled with aforementioned 3,6- diaminoindazole (0.5 mmol) using HBTU as described in general procedure D to afford 2- (pyridin-2-ylamino)-lH-benzimidazole-5-carboxylic acid (3-amino-lH-indazol-6-yl)-amide. MS: m/z 385 (M+H)+.

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

Reference:
Patent; TRANSTECH PHARMA, INC.; WO2007/95124; (2007); A2;,
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