Category: nitriles-buliding-blocks

Application of 40497-11-8, A common heterocyclic compound, 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, molecular formula is C7H8N2O2, 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.

Add 0.01 mol of 3-bromoaniline and a small amount of ethanol to a 250 mL round bottom three-necked flask.Under ice bath, 3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise with stirring.Dissolve 0.018 mol of sodium nitrite in 10 mL of water and slowly drip into the flask.After the completion of the dropwise addition, the reaction was carried out for 0.5 h to obtain a yellow diazonium salt solution.Add 0.01 mol of ethyl 2,3-dicyanopropionate to a three-necked flask.The prepared diazonium salt solution was dropped into the flask, and the reaction was added dropwise for 2 hours.Ammonia water was added, the pH was adjusted to 9-10, and the reaction was carried out for 2 h at room temperature.After completion of the reaction, the mixture was extracted with 40 mL of dichloromethane, and the organic layer was washed with water (2¡Á30 mL), and washed with a saturated sodium chloride solution (1¡Á40 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. Yield 70.1%,

The synthetic route of 40497-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Tech University; Wan Rong; Chen Fuli; Han Zhenyu; Fu Xiaohuan; Jiang Peng; (17 pag.)CN108203450; (2018); A;,
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Synthetic Route of 796600-15-2, 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 796600-15-2 as follows.

Example 1; 2-chloro-4-((1R,2S)-2-hydroxy-1-(5-phenyl-1,3,4-oxadiazol-2-yl)propylamino)-3-methylbenzonitrile; Intermediate 1a; (2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid; 2-chloro-4-fluoro-3-methylbenzonitrile (CAS 796600-15-2, 45g, 265.4 mmol) was mixed together with H-D-Thr-OH (37.92 g, 318.4 mmol) in DMSO (250 mL). K2CO3 (73.35 g, 530.7 mmol) was added to the reaction mixture and the reaction mixture stirred at 75 C. for 24 h. The reaction mixture was cooled to room temperature and poured slowly into a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed on silica gel with a gradient of hexanes/EtOAc and then with EtOAc, 100% to get the purified final product (39.0 g, 54%) 1H NMR (500 MHz, Acetone-d6, delta in ppm) 7.49 (d, J=9 Hz, 1H), 6.70 (d, J=9 Hz, 1H), 5.38 (d, J=10 Hz, 1H), 4.47 (d, J=6 Hz, 1H), 4.25 (m, 1H), 2.34 (s, 3H), 1.33 (d, J=6 Hz, 3H).

According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Miller, Chris P.; US2009/253758; (2009); A1;,
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Related Products of 4592-94-3, These common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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.

General procedure: To the 1 mol eq. of 3-aryl-3-oxopropanonitrile (2) was added1 mol eq. of hydrazine hydrate (1) in Toluene/EtOH (9:1) and thereaction mixture was refluxed for 30 min then another 1 mol eq. ofdifferent 3-aryl-3-oxopropanonitrile (2) and catalytic amount ofPTSA (0.01 mol eq.) was added. Again reaction mixture wasrefluxed up to 4 h. On completion of the reaction, excess solvent was distilled off. The solid so obtained was filtered and washedwith cold ethanol. Solid was neutralised with aq. sodium bicarbonatesolution and again filtered. Compound thus obtained wasair dried and recrystallized from ethanol.

The synthetic route of 4592-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aggarwal, Ranjana; Singh, Gulshan; Kaushik, Pawan; Kaushik, Dhirender; Paliwal, Deepika; Kumar, Ajay; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 326 – 333;,
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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 34916-10-4 as follows. Formula: C7H9NO

Example 77 Ethyl 2-(4-cyanocyclohexylidene)acetate; [0411] To a dispersion of sodium hydride (132 mg, 5.51 mmol) in THF (15 mL), triethyl phosphonoacetate (1.10 mL, 5.51 mmol) was added dropwise. The mixture was stirred until it was colorless before 4-oxocyclohexanecarbonitrile (Astrazeneca AB, see WO2007/13848 Al , 2007)(617 mg, 5.01 mmol) was added. The solution was stirred at ambient temperature until the reaction was complete (TLC). The reaction was quenched by the addition of saturated aqueous NH4CI and the aqueous layer was extracted with ethyl acetate (2 x 40 mL). The combined organic extracts were washed with brine, dried and concentrated. The crude product was used directly in the next step.

According to the analysis of related databases, 34916-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEWLINK GENETICS; MAUTINO, Mario, R.; KUMAR, Sanjeev; JAIPURI, Firoz; WALDO, Jesse; KESHARWANI, Tanay; ZHANG, Xiaoxia; WO2011/56652; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 16532-79-9, name is 4-Bromophenylacetonitrile, 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 16532-79-9, COA of Formula: C8H6BrN

4-bromophenylacetonitrile (23.0 g, 117 mmol) and iodine (29.8 g, 117 mmol) were dissolved in 400 ml of ether,Lower the temperature to -78 C. Sodium methoxide (13.3 g, 246 mmol) dissolved in anhydrous methanol at a concentration of 10 wt% is slowly dropped, the temperature is raised to 0 C, and the mixture is stirred for 4 hours. After the reaction was completed by adding 5% HCl (Hydrochloric acid) aqueous solution, the mixture was filtered, washed with water and cold methanol, and then recrystallized from chloroform and methanol to obtain a white solid .

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

Reference:
Patent; LG Chemical Co., Ltd; Kim, Jin Suk; Choi, Chung-min; Bae, Jae-Sung; Lee, jae cheol; Lee, Ji Young; Jo, Geun; (30 pag.)KR101595147; (2016); B1;,
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Adding a certain compound to certain chemical reactions, such as: 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, 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 20925-27-3, Application In Synthesis of 4-Amino-2-chlorobenzonitrile

Step 1: Synthesis of 2-chloro-4-isothiocyanatobenzonitrile (B) To a stirred solution of 4-amino-2-chlorobenzonitrile (A, 1 g, 6.55 mmol) in dichloromethane (9 mL) was added sodium bicarbonate (2.21 g, 26.31 mmol) and water (9 mL). The resulting mixture was cooled to 0 C., to which thiophosgene (817 mg, 7.11 mmol) was added in drop wise in 30 min at 0 C. The resulting mixture was then warmed up to room temperature and stirred at room temperature for 1 hour. The reaction mixture was diluted with dichloromethane (200 mL), washed with brine (50 mL*2), dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give a crude residue. The residue was purified by flash silica gel chromatography (eluent: ethyl acetate/petroleum ether (v:v=1:30)) to give desired product (yield: 71%)1HNMR (400 MHz, CDCl3): delta 7.69 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.28 (m, 1H);

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; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
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Related Products of 17417-09-3, 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 17417-09-3 as follows.

Example 11 1-(3′-Aminobenzisoxazol-5′-yl)-3-methyl-5-[(2′-aminosulfonyl-[1,1′]-biphen-4-yl)aminocarbonyl]pyrazole To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g) in ethylacetate (50 mL) was added stannous chloride dihydrate (27.0 g). The mixture was brought to reflux for 1.5 h and allowed to cool. The mixture was partitioned between ethyl acetate and sodium bicarbonate (sat. in water). The aqueous phase was extracted with ethyl acetate four times. The organic phase was washed with 4xH2O, dried over sodium sulfate, filtered and concentrated to leave 4-fluoro-3-cyanoaniline (1.40 g). CI mass spectrum z (rel. intensity) 137 (M+H, 100).

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP991638; (2005); B1;,
Nitrile – Wikipedia,
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Electric Literature of 3672-47-7, The chemical industry reduces the impact on the environment during synthesis 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, I believe this compound will play a more active role in future production and life.

To a stirred solution of 0.30 g (1.71 mmol) 3-(4-methoxy-phenyl)- 3-oxo-propionitrile in 10 ml ethanol was added 0.17 ml (1.71 mmol) cyclohexanone, 53 mg (1.71 mmol) sulfur, EPO and 0.14 ml (1.71 mmol) morpholine. The mixture was heated at 40 0C for the week end, and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 0.51 g (85%) (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-(4- methoxy-phenyl)-methanone as an orange solid. ES-MS m/e (%): 288 (M+H+, 100).

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-(4-Methoxyphenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; WO2006/63732; (2006); A1;,
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Synthetic Route of 621-03-4,Some common heterocyclic compound, 621-03-4, name is 2-Cyano-N-phenylacetamide, molecular formula is C9H8N2O, 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.

c) 5-amino-4-methyl-7-oxo-N-phenyl-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide Under argon 46 mg sodium hydride (1 .15 mmol, 60% in mineral oil) in 2 mL DMF were cooled to 0 C and 94 mg 2-cyano-N-phenylacetamide (0.58 mmol) were added in small portions within 15 minutes, the resulting solutino was stirred for another 30 minutes at r.t., then cooled to 0 C and 97 mg 1 -methyl-1 H-thieno[3,2-d][1 ,3]oxazine-2,4-dione (0.52 mmol) were added in portions within 5 minutes and the mixture was stirred for 60 minutes. To this solution 0.58 mL aqueous hydrochloric acid (1 .15 mmol) were added and the resulting yellow suspension was stirred for 10 minutes. The mixture was poured on icecold potassium bicarbonate solution (10%, w/v), stirred for 30 minutes, filtered and the solid washed with water, diethylether / pentane (3:2, v/v), pentane and dried to yield 68 mg 5-amino-4-methyl-7- oxo-N-phenyl-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (0.21 mmol, 40%) as a yellow solid. ESI-MS [M+H] + 300.2 1H-NMR (400 MHz, D6-DMSO): delta (ppm) = 7.97-7.80 (m, 1 H), 7.61 -7.49 (m, 2H), 7.43-7.27 (m, 2H), 7.17-7.07 (m, 1 H), 6.94-6.81 (m, 1 H), 3.03-2.91 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Cyano-N-phenylacetamide, its application will become more common.

Reference:
Patent; NOVARTIS AG; REINHARDT, Juergen; SCHMIEDEBERG, Niko; SPANKA, Carsten; WO2015/186061; (2015); A1;,
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Application of 2032-34-0,Some common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, molecular formula is C7H13NO2, 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 round bottom flask was added the methane sulfonic acid salt of methyl l-amino-4-bromo-lH-pyrrole-2-carboxylate (140 g, 0.444 mol), isopropanol (700 mL) and 3,3- diethoxypropionitrile (128 g, 0.888 mol). The reaction mixture was slowly brought to 85 C over 1 hour and then stirred at 85 C for 2 hours. At this time, the ethanol that was generated and the isopropanol was removed under vacuum. The resulting residue was dissolved in CH2CI2 and washed with water and brine solution. The organic layer was separated, dried over Na2S04, filtered and concentrated. The resulting residue was transferred into a 2L round bottom flask and dichloroethane (900 mL) and DBU (210 gm, 1.36 mol) were successively added to the reaction mixture. The resulting mixture was then stirred at 85 C for 5 hours then cooled to rt and diluted with CH2CI2 followed by washing with water then brine solution. The organic layer was separated, dried over Na2S04, filtered and concentrated. The resulting residue was purified by flash silica gel column chromatography to yield 58 g of title compound as the crude product containing residual DBU. This material was used as is in the next transformation. LCMS (condition A) m/z = 236.0 -ve. XH NMR (400MHz, DMSO-d6) delta ppm: 9.76 (1H, br.s), 7.62 (1H, s), 7.39 (1H, d, 2.0Hz), 6.43 (lH,d, 2.0 Hz). The product is contaminated with DBU and was used directly as such without further purification in the next step.

The synthetic route of 2032-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; BROWN, Gregory D.; DOWEYKO, Lidia M.; DUAN, Jingwu; GUO, Junqing; HYNES, John; JIANG, Bin; KEMPSON, James; LIN, Shuqun; LU, Zhonghui; SPERGEL, Steven, H.; TOKARSKI, John S.; WU, Hong; YANG, Bingwei Vera; WO2012/125886; (2012); A1;,
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