Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, 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 26391-06-0, HPLC of Formula: C7H12N2O

To a solution of N,N-diethylcyanoacetamide (14.1 g, 0.1 mol) in toluene (100 mL) was added IRA 96 resin (0.2 g) and 2-methoxy-5-nitrobenzaldehyde (18.1 g, 0.1 mol). Then the mixture was heated to reflux, released water being collected azeotropically, until TLC test showed the absence of starting materials. The reaction mixture was filtered hot. The filtrate was evaporated completely and the residue was purified with ethanol to afford 1o. (2.2 g, 73 %) as a white solid; mp 134-135 C (EtOH); numax (liquid film) 3074, 2934, 2212, 1633, 1518, 1342 cm-1; deltaH (400 MHz, CDCl3) 1.2 (6H, br s (CH3)3), 3.5 (4H, br s, (CH2)2), 4.0 (3H, s, OMe), 7.0 (1ArH, d, J 9.2 Hz), 7.94 (1H, s, vinyl), 8.3 (1ArH, dd, J 9.2, 2.3 Hz), 9.0 (1ArH, d, J 2.4 Hz); m/z 303.2 (MH+).

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:
Article; Harisha, Attimogae Shivamurthy; Nayak, Suresh Parameshwar; Nagarajan, Kuppuswamy; Row, Tayur Narasingarow Guru; Hosamani, Amar A.; Tetrahedron; vol. 72; 22; (2016); p. 2880 – 2889;,
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Related Products of 79463-77-7, 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 79463-77-7 as follows.

A mixture of 3-aminobenzotrifluoride (15 g, 93 mmol) and diphenyl cyanocarbon-imidate (22.2 g, 93 mmol) was heated at reflux in THF (100 ml) for 20 h. The r.m. was then concentrated under reduced pressure. H2O was then added and the resulting solid was filtered and dried in vacuo, yielding 20.7 g of intermediate 35 (72%).

According to the analysis of related databases, 79463-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Van Brandt, Sven Franciscus Anna; De Cleyn, Michel Anna Jozef; Gijsen, Henricus Jacobus Maria; Berthelot, Didier Jean-Claude; Surkyn, Michel; US2012/295891; (2012); A1;,
Nitrile – Wikipedia,
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5922-60-1, name is 2-Amino-5-chlorobenzonitrile, 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. Formula: C7H5ClN2

Example 4 – synthesis of 4-amino-6-chloro-quinazolineA solution of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol) in formamide (20 ml) was heated at 180 0C for 6 hours. After cooling to room temperature, water (30 ml) was added to the reaction mixture. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a grey solid (1.2 g, yield: 95 percent) which was characterized by its mass spectrum as follows: MS (m/z): 180 ([M+H]+, 100).

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2008/9077; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, 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. HPLC of Formula: C7H3BrClN

A flask which had been dried by heating and flushed with argon was initially charged with 1.0 eq. of the appropriate boronic acids, 1.0 eq. of the aryl bromide or aryl iodide, 3.0 eq. of potassium carbonate and 0.1 eq. of [1,1 -bis(diphenylphosphino)ferrocenelpalladium(II) chloride/monodichloromethane adduct or tetrakis(triphenylphosphine)palladium(0). The flask was then evacuated three times and in each case vented with argon. Dioxane (about 6 ml/mmol) was added, and the reaction mixture was stirred at 110 C. for a number of hours until substantially complete conversion had been achieved. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue. After addition of ethyl acetate and phase separation, the organic phase was washed once with water and once with saturated aqueous sodium chloride solution, dried (sodium sulphate or magnesium sulphate), filtered and concentrated under reduced pressure. The crude product was then purified either by means of normal phase chromatography (cyclohexane/ethyl acetate mixtures or dichloromethane/methanol mixtures) or preparative RP-HPLC (water/acetonitrile gradient or water/methanol gradient).

The synthetic route of 2-Bromo-4-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; US2018/346424; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. SDS of cas: 154607-01-9

3-Chloro-2′,4′-difluorobiphenyl-4-carbonitrile (EM-4283): In a round bottom flask, 4-bromo-2-chlorobenzonitrile (3 g, 13.85 mmol), 2,4-difluorophenylboronic acid (2.63 g, 16.63 mmol) and K3PO4 (8.83 g, 41.56 mmol) were added in dry DMF (50 mL). The mixture was purged under argon for 30 min and Pd(PPh3)4 (1.6 g, 1.38 mmol) was added. The mixture was heated for 48 hr at 80 C. Water (100 mL) was added and the aq layer was extracted with CH2Cl2(3*50 mL). The organic layer was washed with brine (3*50 mL), dried, evaporated and purified on silica gel (EtOAc/hexanes:1/19) to give the product (1 g, 29%), 1H.NMR (acetone-d6) delta: 7.2-7.28 (m, 2H), 7.72-7.79 (m, 2H), 7.91 (t, 1H, J=1.4 Hz), 8.02 (d, 1H, J=8.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 154607-01-9, its application will become more common.

Reference:
Patent; Endorecherche, Inc.; US2004/6134; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 55984-93-5, name is 2-Methylterephthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Methylterephthalonitrile

Step 2. 2-[(E)-2-(dimethylamino)ethenyl]benzene-1,4-dicarbonitrileInto a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-methylbenzene-1,4-dicarbonitrile (4 g, 28.14 mmol, 1.00 equiv), [(tert-butoxy)(dimethylamino)methyl]dimethylamine (9.8 g, 56.23 mmol, 2.00 equiv) in N,N-dimethylformamide (50 mL). The resulting solution was stirred overnight at 75° C., and then it was concentrated under vacuum. The resulting mixture was washed with 50 mL of hexane. The solids were collected by filtration. This provided 5.3 g (95percent) of 2-[(E)-2-(dimethylamino)ethenyl]benzene-1,4-dicarbonitrile as a yellow solid.

The synthetic route of 55984-93-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 928118-07-4, 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. 928118-07-4, name is 3,4-Dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 15 : 4- [5-(3-Morpholin-4-yl-phenoxy)pyridin-2-yl] -3,4-dihydi benzo[l,4]oxazine-6-carboni rile A suspension of 4-{3-[(6-chloropyridin-3-yl)oxy]phenyl}morpholine (200mg, 0.689mmol), 3,4-dihydro-2H-benzo[l,4]oxazine-6-carbonitrile (HOmg, 0.689 mol), in’5′(dibenzylideneacetone)palladium(0) (31mg, 0.034mmol), 4,5-bis,(diphenyl- phosphino)-9,9-dimethylxanthene (30 mg, 0.068mmol) and cesium carbonate (449mg, 1.379mmol) in de-gassed 1,4-dioxane (5mL) was heated at 80C for 2 days. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by column chromatography using ethyl acetate:hexane (7:3) as the mobile phase to afford 4-[5-(3-Morpholin-4-yl-phenoxy)pyridin-2-yl]-3,4- dihydro-2H-benzo[l,4]oxazine-6-carbonitrile (HOmg, 39%) as a white solid.Mass: (ES+) 415(M+H)+ HPLC: 98.7%NMR: deltaEta ( 6-DMSO) 3.12 (4H, m), 3.72 (4H, m), 3.94 (2H, m), 4.34 (2H, m), 6.40 (1H, dd), 6.55 (1H, br s), 6.74 (1H, dd), 7.04 (1H, d), 7.22 (1H, t), 7.30 (2H, m), 7.47 (1H, dd), 7.82 (1H, d) and 8.65 (1H, d).

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-Dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David Christopher; SCOPES, David Ian Carter; WO2011/144578; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 630-18-2, name is Pivalonitrile, 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. Recommanded Product: 630-18-2

General procedure: To an ice cold solution of pivalonitrile (1f, 120 muL, 1.085 mmol) in Et2O (1.0 mL)was added an ethereal solution of 2-naphthylmagnesium bromide (2b, 0.75 M, 1.88mL, 1.410 mmol) and the reaction mixture was stirred at 60 C in a sealed tube for 2 h.After cooling to 0 C, the reaction mixture was treated with anhydrous MeOH (132muL), followed by the addition of CuBr2 (24.3 mg, 0.109 mmol) and anhydrous DMF(10.0 mL). The resulting reaction mixture was stirred at 80 C under an oxygenatmosphere for 6 h. Then the reaction was quenched by the addition of pH 9ammonium buffer solution and the organic materials were extracted with Et2O. Thecombined organic extracts were washed with water, and then with brine and driedover anhydrous MgSO4. The solvents were removed in vacuo and the resulting crudematerial was purified by flash column chromatography using hexane-EtOAc (90:10)to afford 2-naphthonitrile

The synthetic route of Pivalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tnay, Ya Lin; Ang, Gim Yean; Chiba, Shunsuke; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1933 – 1943;,
Nitrile – Wikipedia,
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Reference of 127946-77-4, 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. 127946-77-4 name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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.

A vial was charged with (1 R,2R)-2-(2-(4,4-difluoropiperidin- 1 -yl)-5 -(4-( 1,1 – dioxidothiomorpholino)phenyl)thiazol-4-yl)cyclohexanecarboxylic acid (42.1 mg, 0.078 mmol), 1 -aminocyclopropanecarbonitrile hydrochloride (23.12 mg, 0.195 mmol), DMF (780 tl), DIPEA (68.1 tl, 0.390 mmol), and HATU (37.1 mg, 0.098 mmol). The resulting mixture was stirred at70 C for 7 hours. Reaction mixture was cooled to RT and purified directly by reverse phase preparative HPLC (H20/ MeCN (10-95%), 0.1% TFA, 20 mm) giving 29mg (61.6%) of (1 R,2R)-N-( 1 -Cyanocyclopropyl)-2-(2-(4,4-difluoropiperidin- 1 -yl)-5 -(4-( 1,1 – dioxidothiomorpholino)phenyl)thiazol-4-yl)cyclohexanecarboxamide (Compound 6) as white solid: MS (ES, m/z): 604.3 (M + 1); ?H NMR (400 MHz, CDC13): oe 0.87-0.86 (m, 2 H); 1.43-1.28 (m, 5 H); 1.85-1.50 (m, 5H); 2.19-2.05 (brm, 4 H); 2.58 (td, J= 11.4, 3.1 Hz, 1 H); 2.80 (td, J = 11.3, 3.2 Hz, 1 H); 3.13-3.11 (m, 4 H); 3.62-3.58 (m, 2 H); 3.74-3.69 (m, 2 H); 3.91-3.89 (m, 4 H); 5.83 (s, 1 H); 6.91 (d, J = 8.5 Hz, 2 H); 7.28 (d, J = 8.4 Hz, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 6609-56-9, 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 6609-56-9 as follows.

To a nitromethane (0.1 mL) solution of 4-methoxybenzonitrile (1f) (30 mg, 0.225 mmol) were addedH2O (1.0 mL), DBU (69 mg, 0.436 mmol), copper (I) iodide (9 mg, 0.0451 mmol), cesium (I)carbonate (37 mg, 0.113 mmol) at room temperature. The reaction mixture was heated at 100 °C for2 h and then poured into water (50 mL). The organic layer was separated and the aqueous layer wasextracted with AcOEt. The combined organic layer was dried over MgSO4. The solvent wasremoved under reduced pressure. The residue was purified by preparative TLC on silica gel elutingwith AcOEt-n-hexane (1:1) to give 2-methoxybenzamide (2f)S5 (17 mg, 50percent) as pale yellow powders.mp 123-125 °C,

According to the analysis of related databases, 6609-56-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kuwabara, Jun; Sawada, Yoshiharu; Yoshimatsu, Mitsuhiro; Synlett; vol. 29; 15; (2018); p. 2061 – 2065;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts