Month: July 2021

1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. Product Details of 1953-99-7

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.21 g), K2CO3 (3.9 g) and acetone (25 ml) were placed in a 100 ml flask and stirred while heating to 70 ° C. After completion of the reaction, the solid matter is obtained by filtering and distilling off the liquid obtained by washing with acetone. At this time, the obtained solid is dissolved in a small amount of dichloromethane, washed with nucleic acid several times, filtered and vacuum dried to obtain 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Seo Hye-won; Shin Myeong-yeop; Jeong Ui-su; Han Gyu-seok; (56 pag.)KR2019/11995; (2019); A;,
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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Amino-1-cyclopropanecarbonitrile hydrochloride

General procedure: Odanacatib acid 1 (60 mg) was dissolved in 3 mL DMAc and cooled to 0 C. Amine (1.2 eq.) and HATU (59 mg) were added. The resulting solution was stirred for 15 min and DIPEA (68 mL) was added. The reaction was stirred for 2.5h. Water was slowly added dropwise and the slurry was stirred 2.5h at room temperature. The mixture was filtered and the solid material was washed with a 1 :1.2 DMF/water solution, water and 2-propanol. The material was removed from the filter by addition of THF. The filtrate was concentrated and purified by FCC (silica, gradient DCM to 2% MeOH in DCM). The products were obtained as a white solid.According to general procedure A, the reaction between Odanacatib acid 1 (59.8 mg) and 1-amino-cyclopropanecarbonitrile hydrogenchloride (18.5 mg) afforded product ODN as a white solid 1 H NMR (300 MHz, CDCI3) d = 8.03 (d, J = 8.4 Hz, 2H), 7.77 (d, J = 8.8 Hz, 2H), 7.65 (d, J = 8.1 Hz, 2H), 7.48 (d, J = 8.1 Hz, 2H), 7.42 (s, 1 H), 4.17 (q, J = 7.2 Hz, (0199) 1 H), 3.59 (dd, J = 8.9, 3.3 Hz, 1 H), 3.10 (s, 3H), 2.17 – 1.85 (m, 2H), 1.56 – 1.44 (m, 2H), 1.47 (d, J = 21.7 Hz, 3H), 1.44 (d, J = 22.0 Hz, 3H), 1.1 1 – 0.85 (m, 2H). 13C NMR (75 MHz, CDCI3) d = 174.42, 145.69, 140.57, 139.94, 134.53, 129.40, 128.22, 128.20, 126.02 (0200) (q, J = 279.3 Hz), 119.56, 96.84 (d, J = 163.8 Hz), 63.44 (q, J = 29.3 Hz), 59.03, 44.75, 43.64 (d, J = 19.9 Hz), 28.37 (d, J = 24.4 Hz), 25.83 (d, J = 24.7 Hz), 20.21 , 16.86, 16.48. HRMS (ESI+): calculated for C25H28F4N303S [M+H]+ 526.1788, found: 526.1816.

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 127946-77-4.

Reference:
Patent; ACADEMISCH ZIEKENHUIS LEIDEN (H.O.D.N. LUMC); OVAA, Huib; MONS, Maria Wilhelmina Elisabeth; VAN BOECKEL, Stan; (47 pag.)WO2019/112426; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

621-50-1, name is 2-(3-Nitrophenyl)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. Computed Properties of C8H6N2O2

To a solution of 4-(methylamino)-2-(methylsulfanyl)pyrirnidine-5-carbaldehyde (10.0 g, 55 mmol) and (3-nitrophenyl)acetonitrile (10.5 g, 65 mmol) in DMF (150 mL) was added K2CO3 (38 g, 275 mmol) at RT. The mixture was stirred at 100 C for 18h. After cooling, the reaction was diluted with DMF (50 mL) and filtered. The filtrate was concentrated to give crude 8-methyl-2-(methylsulfanyl)-6-(3-nitrophenyl)-8H-pyrido[2,3-d]pyrimidin-7- ylideneamine (9.0 g, 50% yield) which was used in the next reaction without further purification.

The synthetic route of 621-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 108168-88-3, name is N-(tert-Butyl)-2-cyanoacetamide, 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 108168-88-3, COA of Formula: C7H12N2O

Into a 8-mL sealed tube, was placed 3-(2-fluoro-5-formylphenoxy)propanoic acid (20 mg, 0.09 mmol, 1.00 eq.), methanol (0.25 mL), N-tert-butyl-2-cyanoacetamide (13.2 mg, 0.09 mmol, 1.00 eq.), CH3COONH4 (36.3 mg, 0.47 mmol, 5.00 eq.). The resulting solution was stirred for 30 min at 60 C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-l): Column, C18 silica gel; mobile phase, FbC):ACN=99: l increasing to FLO: ACN= 1 :99 within 100 min; Detector, UV 254 nm. This resulted in 5 mg (16%) of 3-[5- [2-(tert-butylcarbamoyl)-2- cyanoeth-l-en-l-yl]-2-fluorophenoxy]propanoic acid as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (171 pag.)WO2019/99576; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 4-Bromo-2-methoxybenzonitrile

To a mixture of 4-bromo-2-methoxy benzonitrile (1 g, 4.72 mmol), butyl vinyl ether (2.362 g, 23.58 mmol), l,3-bis(diphenylphosphino)propane (0.097 g, 0.236 mmol), palladium (II) acetate (0.053 g, 0.236 mmol) and l-butyl-3-methylimidazolium tetrafluoro borate (0.533 g, 2.358 mmol) in DLC/MSO (4.72 ml) was added diisopropylamine (0.807 ml, 5.66 mmol) in a microwave vial. The reaction mixture was degassed with argon and stirred at 115°C for 18h. The mixture was partitioned between EtOAc and H20 and the aqueous layer was extracted with EtOAc (3x). The combined organic phase was washed with brine, dried over anhydrous MgS04, and filtered. The residue was then dissolved in MeOH/DLC/MSO (25ml/5ml), then 3N HC1 (20 ml) was added. The mixture was stirred at rt for 3h. After concentration the residue was partitioned between DCM and water and the aqueous layer was extracted with DCM (3x). The combined organic phase was washed with brine, dried over anhydrous MgS04, and filtered. The filtrate was concentrated and purified by silica gel column chromatography using (0-60)percentEtOAc/Hexanes as mobile phase to give the title product as a pale yellow solid.

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:
Patent; MERCK SHARP & DOHME CORP.; CHOBANIAN, Harry; PIO, Barbara; GUO, Yan; DING, Fa-Xiang; DONG, Shuzhi; WALSH, Shawn, P.; JIANG, Jinlong; KIM, Dooseop; WO2015/95097; (2015); A2;,
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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H3ClF3N

To a flask was added Pd2dba3 (0.405 g), DavePhos (0.6884 g, 1.75 mmol), and CuI (0.1655 g). This was purged with nitrogen and degassed; triethylamine (100 mL) was then added. Benzonitrile (XVII) (36.2 g, 176 mmol) was then added, and the mixture was heated to 65 0C. 3,3-dimethylbutyne (23.7 g, 288 mmol) was then slowly added over 2 hours. The mixture was heated an additional 2 hours, and the heat removed. The mixture was diluted with isopropyl acetate (150 mL) and washed twice with water (150 mL) and twice with 10% aqueous citric acid (150 mL). The organics were diluted with methanol (40 mL), and the volume reduced in vacuo to 60 mL. This was repeated twice with 190 mL methanol, the residual material diluted to 250 g with methanol and used in the next step as a solution. An analytical sample was obtained by removing all the solvent in vacuo.1H NMR (CDCl3, 400 mHz) 7.75 – 7.70 (m, 2H), 7.60-7.55 (m, IH), 1.37 (s, 9H); 13C NMR (CDCl3, 100MHz) 132.6, 128.7, 128.6, 123.8, 123.7, 116.24, 107.96, 75.06, 30.73, 28.64.

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/117626; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 6283-71-2, 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. 6283-71-2 name is Dimethyl 2-cyanosuccinate, 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.

To a solution of dimethyl 2-cyanobutanedioate (CAS 6283-71-2, 10.0 g, 58.4 mmol, 1.00 eq) in methanol (60.0 niL) and water (60.0 mL) was added triethylamine (8.87 g, 87.6 mmol, 12.1 mL, 1 50 eq) at 0- 5 C. After stirring for 30 minutes, ten- butyl prop-2-enoate (CAS 1663-39-4, 8.99 g, 70.1 mmol, 10.2 mL, 1.20 eq) was added to the reaction mixture. The mixture was stirred at 0- 5 C for 1.5 hours and was allowed to warm to 25 C and stirred for a further 2 hours TLC showed that starting material was consumed and one new spot was detected. The reaction mixture was acidified with 2 N aq HC1 to pH = 4 and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over NaiSCX filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (SiC , petrol ether: ethyl acetate = 20: 1 to 4: 1) to afford 4-0-tert-butyl 1-6), 2-O-dimethyl 2-cyanobutane- 1,2, 4- tricarboxylate (10.0 g, 33.4 mmol, 57.2%) as a yellow gum. NMR: 400 MHz, CDCh: d 3.82- 3 87 (m, 3H), 3.73 (s, 3H), 3.09 (d, ./ 17.07 Hz, 11 1 ), 2.83 id, J = 17 32 Hz, i l l), 2 47- 2 61 ( n, (1198) 1H), 2.31- 2.43 (m, 1H), 2.10- 2.25 (m, 2H), 2.03 (s, 1H), 1.43 (s, 9H)

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

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; DEY, Fabian; GOERGLER, Annick; KUHN, Bernd; NORCROSS, Roger; ROEVER, Stephan; SCHMID, Philipp; (270 pag.)WO2019/204354; (2019); 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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-3-fluorophenylacetonitrile

General procedure: To a solution of 3-fluoro-4-bromophenylacetonitrile (2g, 9.2mmol) and 1,2-dibromoethane (0.6ml, 7mmol) in toluene (5ml) was added 50% NaOH (5mL) and TBAB (0.32g , 1 mmol). The mixture was stirred vigorously at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate.The organic solution was washed with 1N HCl and then with brine, dried over anhydrous sodium sulfate and concentrated.Separation by column chromatography (eluent: PE / EA = 20/1, v / v), a yellow solid was obtained with a yield of 91%.

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; He Siyu; Liu Yang; (25 pag.)CN110590548; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(3-Nitrophenyl)acetonitrile

Step a: Synthesis of 2-methyl-2-(3-nitrophenyl)propanenitrile To an ice-cold slurry of 50% NaH (6.84 g, 171 mmol) in anhydrous THF (30.0 ml) was slowly added a solution of 2-(3-nitrophenyl)acetonitrile (4.2 g, 25.9 mmol) in anhydrous THF (30 ml). After 30 min, methyl iodide (12.63 ml, 202 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was then quenched with ice-water. The reaction mixture was then extracted with ethyl acetate, the organic layer was separated and washed with water, dried over anhydrous sodium sulphate; filtered and concentrated to get crude oil. The crude oil was purified by column chromatography over silica gel by eluting with ethyl acetate/hexane (5:95) gave 2-methyl-2-(3-nitrophenyl) propanenitrile (2.1 g). 1HNMR (400 MHz, CDCl3), delta 8.33-8.32 (m, 1H), 8.24-8.21 (m, 1H), 7.92-7.89 (m, 1H), 7.63 (t, J=8.00 Hz, 1H), 1.82 (s, 6H). GCMS:190.11[M+]

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:
Patent; Dave, Bhavesh; Banerjee, Rakesh Kumar; Phukan, Samiron; Khoje, Abhijit Datta; Hangarge, Rajkumar; Jadhav, Jitendra Sambhaji; Palle, Venkata P.; Kamboj, Rajender Kumar; US2015/133424; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6575-00-4, name is 3,5-Dichlorobenzonitrile, 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 6575-00-4, COA of Formula: C7H3Cl2N

To a 250 mL round bottom flask charged with 3,5-dichlorobenzonitrile (42; 7.31 g; 34.90 mmol) and maintained under an argon atmosphere was added DMF (70 mL). The flask was cooled to 0 C. and powdered sodium methoxide (1.88 g; 34.90 mmol) was added in two portions 15 min apart. The homogeneous mixture was allowed to warm to room temperature and stirred for 24 h. The solution was cooled to 0 C. and aqueous 10% HCl (20 mL) was added dropwise via an addition funnel after which the reaction was warmed to RT. The mixture was extracted with EtOAc and the combined extracts washed sequentially with water and brine. The organic phase was dried (Na2SO4), filtered, and volatile solvents were removed in vacuo. The resulting solid was recrystallized from hexanes to afford 3-chloro-5-methoxybenzonitrile (43, 4.2 g; 72%).

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, 3,5-Dichlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2005/234236; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts