Tag: M.W=100-200

Related Products of 1558-81-2,Some common heterocyclic compound, 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, molecular formula is C7H9NO2, 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.

A) To a solution of 1-methyl-1H-pyrazol-3-amine (223 mg) in cyclopentyl methyl ether (5.0 mL) was added ethyl 1-cyanocyclopropanecarboxylate (0.90 ml). The reaction mixture was stirred at 120 C. for 30 hr, and diluted with ethyl acetate. The diluted solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (237 mg). MS (ESI+): [M+H]+190.8.

The synthetic route of 1558-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Yoshida, Masato; TAKAMI, Kazuaki; TOMINARI, Yusuke; SHIOKAWA, Zenyu; SHIBUYA, Akito; SASAKI, Yusuke; GIBSON, Tony; TAKAGI, Terufumi; US2015/133451; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 5216-17-1, name is 2,3,5,6-Tetrafluorobenzonitrile, 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. Quality Control of 2,3,5,6-Tetrafluorobenzonitrile

[0154] NaH (60% in mineral oil, 128 mg, 3.2 mmol) was slowly added to a solution of 2,3-dihydroimidazo[1,2-cjquinazolin-9-ol (300 mg, 1.6 mmol) in THF (10 mL) at 0 C. The reaction mixture was degassed with N2 and stirred at 0 C for 30 mm. Then 2,3,5,6- tetrafluorobenzonitrile (308 mg, 1.8 mmol) was added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched by MeOH (5 mL) at 0 C. The resulting mixture was evaporated and the residue was purified on silica gel column flash chromatography (DCM/MeOH from 60:1 to 10:1, v/v) to afford 2-((2,3-dihydroimidazo[1,2- cjquinazolin-9-yl)oxy)-3,5,6-trifluorobenzonitrile (200 mg, 36% yield) as a yellow solid.

The synthetic route of 2,3,5,6-Tetrafluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABM THERAPEUTICS, INC.; CHEN, Chen; (154 pag.)WO2019/60611; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 72291-30-6,Some common heterocyclic compound, 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, molecular formula is C6H9NO2, 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 solution of 122-1 (2.0 g, 15.73 mmol, 1 eq), (Boc)20 (6.87 g, 31.46 mmol, 7.23 mL, 2 eq) and NiCl2 (203.9 mg, 1.57 mmol, 0.1 eq) in MeOH (40 mL) at 0C was added NaBH4 (4.17 g, 110.11 mmol, 7 eq) slowly portion-wise, and the resulting mixture was stirred at 20C for 16 h. The reaction mixture was quenched with NH4.H20 (10 mL), and then concentrated to remove solvent. And the residue was diluted with water (50 mL), and then extracted with EA (50 mL *3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography to give 122-2 (600 mg, 2.59 mmol, 16.5% yield). 1H NMR (400 MHz, CDCI3) d 4.97 (brs, 1H), 3.69 (s, 3H), 3.24 (d, J= 6.6 Hz, 2H), 1.44 (s, 9H), 1.19 (s, 6H).

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

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (559 pag.)WO2019/222431; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 92664-05-6, name is Potassium 1-cyano-3-ethoxy-2,3-dioxopropan-1-ide, 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 92664-05-6, SDS of cas: 92664-05-6

To a stirring suspension of crude 5-hydrazinylisoquinoline (prepared from Example 25 step a, 6.0 g, 37.7 mmol) and potassium 1-cyano-3-ethoxy-3-oxoprop-1-en-2-olate (8.1 g, 45.2 mmol) in ethanol (36 mL) was added a solution of 6 N aqueous hydrochloric acid (7.7 mL, 45.2 mmol) and deionized water (10 mL). The reaction mixture was heated at 90 C. for 5 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resulting residue was extracted with 2:1 chloroform/iPrOH. The organic layer was washed with aqueous saturated sodium bicarbonate and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting solid was suspended in dichloromethane/diethyl ether and the yellow solid was collected by filtration to give the desired product (3.14 g, 11.1 mmol, 30%).

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, Potassium 1-cyano-3-ethoxy-2,3-dioxopropan-1-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Junfa; FAN, Pingchen; KRASINSKI, Antoni; LI, Lianfa; LUI, Rebecca M.; McMAHON, Jeffrey P.; POWERS, Jay P.; ZENG, Yibin; ZHANG, Penglie; US2013/225580; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

501-00-8, name is 2-(3-Fluorophenyl)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. Product Details of 501-00-8

General procedure: General procedure for the reduction of nitrile by KBH4and CuCl2:To a 10 mL round-bottomed flask was added 2-(4-chlorophenyl)acetonitrile (0.1 5 g, 1 mmol), KBH4 (0.17 g, 3mmol), CuCl2 (0.03 g, 0.25 mmol) and 80 % isopropanol (1.6mL isopropanol and 0.4 mL water). The reaction completed in8 h at 60 C as evidenced by TLC (DCM:MeOH 10:1). Thereaction mixture was cooled to 25 C and removed the solvent.Ethyl acetate (5 mL) was added to the residue, washed withwater (1 mL) and brine (1 mL). The organic layer were dried withanhydrous Na2SO4, filtered and evaporated in vacuo to affordthe crude product.

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Han; Hu, Jialei; Xu, Xinliang; Zhou, Yifeng; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3564 – 3566;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 6136-93-2,Some common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, molecular formula is C6H11NO2, 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 stirred solution of 2,2-diethoxyacetonitrile (XIX) (0.59 g, 4.57 mmol) in a vial containing MeOH (4.57 mL) was added MeONa (0.1 mL, 0.46 mmol) dropwise. The reaction was stirred at 35 C. for 20 h. HOAc was added (26.1 muL, 0.46 mmol) (checked that the pH is 7-8 using pH strips) followed by (4-bromo-3-chloro-phenyl)methanamine (XXII) (1.01 g, 4.57 mmol). The mixture was stirred at 35 C. for 40 h. The solvent was removed under vacuum. Sulfuric Acid (7.43 mL, 137.0 mmol) was then added and stirred at 35 C. for 16 h. NH4OH (60.6 mL, 141.6 mmol) was added at 0 C. The reaction was filtered through Celite and purified by C18 silica gel (240 g) [0?30% H2O/MeCN (0.1% Formic acid)] to produce a 1:1 mixture (by NMR) of 6-bromo-7-chloro-isoquinolin-3-amine (XXIII) and 6-bromo-5-chloroisoquinolin-3-amine (XXIV) (633.7 mg, 2.46 mmol, 53.9% yield). 1H NMR (499 MHz, DMSO-d6) delta ppm 6.23 (2H, s), 6.46 (2H, s), 6.57 (1H, s), 6.83 (1H, s), 7.40 (1H, d, J=8.51 Hz), 7.74 (1H, d, J=8.51 Hz), 8.05 (1H, s), 8.09 (1H, s), 8.81 (1H, s), 8.88 (1H, s); ESIMS found for C9H6BrClN2 m/z 256.9 (79BrM+H).

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

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Eastman, Brian Walter; Cao, Jianguo; Mittapalli, Gopi Kumar; (82 pag.)US2019/125741; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature 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.

2-Fluoro-5-nitrobenzonitrile (500 mg, 3.01 mmol), triazole (228.7 mg, 3.31 mmol) and K2CO3 (832.0 mg, 6.02 mmol) were added to THF (10 mL) and stirred at 25 C. for 16 h. The reaction mixture was filtered and the residue was washed with ethyl acetate (30 mL*3). The combined organic layers were concentrated under reduced pressure to afford a crude yellow solid. The crude solid was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100:0 to 50:50) to afford 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile, 11a (500 mg, 77.2%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.74 (d, J=2.6 Hz, 1H), 8.65 (dd, J=2.4, 9.0 Hz, 1H), 8.48 (d, J=0.9 Hz, 1H), 8.27 (d, J=9.0 Hz, 1H), 7.98 (d, J=0.9 Hz, 1H).

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; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 17626-40-3,Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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.

Step 1: 1H-benzo[d]imidazole-5-carbonitrile3, 4-Diaminobenzonitrile (1.0 g; 7.5 mmol) was dissolved in formic acid (3 ml_) and heated at 100C for 1.5 hours. The mixture was cooled, neutralised with 10% sodium hydroxide and the resulting precipitate isolated by filtration and dried in vacuo to yield the title compound as a brown solid (890 mg; 82%). 1H NMR (DMSO-de) delta 8.50 (1 H, s), 8.19 (1 H, s), 7.79 (1 H, d, J= 8.3 Hz), 7.62 (1 H, dd, J = 8.3, 1.54 Hz). LC/MS (Method C): 144 (M+H) HPLC (Method F) Rt = 2.14 min (Purity: 99.4%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Diaminobenzonitrile, its application will become more common.

Reference:
Patent; MERCK SERONO S.A.; WO2009/80663; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 64829-31-8, name is 3-Methoxy-4-methylphenylacetonitrile, molecular formula is C10H11NO, 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. Formula: C10H11NO

A 40 mL scintillation vial was charged with compound 79 (250 mg, 1.55 mmol), NBS (331 mg, 1.86 mmol), AIBN (50.9 mg, 0.31 mmol) and CCl4 (5 mL). The reaction mixture was stirred at 70 C. for 2 h. After cooling, the reaction mixture was evaporated to dryness. Flash chromatography (24 g column, 0 to 40% EtOAc in hexanes) gave compound 80 (189 mg, 0.787 mmol, 51% yield) as a solid. LC-MS (ES, m/z): No ion detected. 1H NMR (400 MHz, CDCl3) delta 7.33 (d, J=7.7 Hz, 1H), 6.88 (d, J=7.7 Hz, 1H), 6.84 (s, 1H), 4.53 (s, 2H), 3.92 (s, 3H), 3.74 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64829-31-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; GANGWAR, Sanjeev; HE, Liqi; SIVAPRAKASAM, Prasanna; BROEKEMA, Matthias; COX, Matthew; TARBY, Christine M.; ZHANG, Qian; (75 pag.)US2020/38403; (2020); 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. 35747-58-1, name is 5-Amino-2-chlorobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5ClN2

Reference Example 9b 2-chloro-5-piperazin-1-yl benzonitrile 3-Cyano-4-chloroaniline (10.1 g, 66 mmol), as prepared in Reference Example 9a, was dissolved in n-butanol (300 mL) bis-(2-chloroethyl)amine hydrochloride (23.2 g, 130 mmol) and potassium iodide (50 mg, catalytic) were added. The mixture was heated at reflux for three days, then cooled in a refrigerator overnight. A solid precipitate was collected by filtration, washed with cold n-butanol and dried. The crude product was distributed between methylene chloride and 2N ammonium hydroxide. The organic layer was separated, dried (Na2SO4) and concentrated to yield a light yellow solid (9.1 g, 59%) which gave a single peak by GC and TLC analysis.

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; Pierson, Edward; Sohn, Daniel; Haeberlein, Markus; Davenport, Timothy; Chapdelaine, Marc; Horchler, Carey; McCauley, John P.; US2003/13708; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts