Tag: M.W=100-200

Reference of 63968-85-4,Some common heterocyclic compound, 63968-85-4, name is 2-(Trifluoromethoxy)benzonitrile, molecular formula is C8H4F3NO, 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 mixture of2-(trifluoromethoxy)benzonitrile (0.342 mL, 1.999 mmol) and sodium borodeuteride (192mg, 4.60 mmol) in THF (10 mL) at 0 C was added over 45 mm, iodine (507 mg, 1.999mmol) as a solution in THF (4 ml). The reaction mixture was refluxed for 2 h. At thistime, it was cooled to 0 C and 6 N HC1 (2 ml) was carefully added. This mixture wasrefluxed for 30 mm. After cooling to rt, the mixture was partitioned between EtOAc (40ml) and iN NaOH (40 ml). The organic layer was washed with water (20 ml) and brine(20 ml). After drying (Na2504) and filtration, the organic layer was concentrated toafford 2-(trifluoromethoxy)dideuterobenzylammne (385 mg, 1.993 mmol, 100 % yield) asa light yellow oil. The material was impure and was used crude in the coupling step.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUO, Junqing; HART, Amy, C.; MACOR, John, E.; MERTZMAN, Michael, E.; PITTS, William, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; CHEN, Jie; DZIERBA, Carolyn, Diane; LUO, Guanglin; SHI, Jianliang; SIT, Sing-Yuen; (428 pag.)WO2018/148626; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, 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 868-54-2, name: 2-Aminoprop-1-ene-1,1,3-tricarbonitrile

General procedure: Et3N (0.3 mmol) was added to a stirred solution of salicylaldehyde (3 mmol), 2-aminoprop-1-ene-1,1,3-tricarbonitrile (3 mmol) and 3-trifluoromethyl-2-pyrazolin-5-one in 5 ml of n-PrOH at ambient temperature. Then mixture was refluxed for 4 h. After the reaction was finished and cooled the solid was filtered and dried to isolate pure substituted 2,4-diamino-5-(5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile. In some cases cristallisation from EtOH-DMSO is needed.

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; Elinson, Michail N.; Vereshchagin, Anatoly N.; Anisina, Yuliya E.; Fakhrutdinov, Artem N.; Goloveshkin, Alexander S.; Egorov, Mikhail P.; Journal of Fluorine Chemistry; vol. 213; (2018); p. 31 – 36;,
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Reference of 59997-51-2, 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. 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step j03:[0668]At room temperature 4,4-dimethyl-3-oxopentanenitrile (J-II) (1 equivalents, 5 g) was taken up in ethanol (100 mL), mixed with hydrazine hydrate (2 equivalents, 4.42 g) and refluxed for 3 h. The residue obtained after removal of the ethanol by distillation was taken up in water (100 mL) and extracted with ethyl acetate (300 mL). The combined organic phases were dried over sodium sulfate, the solvent was removed under vacuum and the product (JAI) (5 g, 89% yield) was obtained as a light red solid after recrystallisation from n-hexane (200 mL).

The synthetic route of 4,4-Dimethyl-3-oxopentanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
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Reference of 2338-75-2,Some common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, molecular formula is C9H6F3N, 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 50 mL of anhydrous ethnol was added NaOH (160 mg,4 mmol), 2-formyl pyrrole (380.4 mg, 4 mmol) and 4-trifluoromethyl benzyl cyanide (624 muL, 4 mmol). The reaction was heated to reflux with stirring for 3 h. After cooled to room temperature, the reaction solution was evaporated in vacuum. The residue was purified by silica gel column (hexane:ethyl actate = 40: 1) to give 10b as yellow solid ( 596 mg, 56.9%). 1H NMR (400MHz, CDCl3), delta 9.82 (s, 1H), 7.70-7.65 (m, 4H), 7.48 (s, 1H), 7.12-7.11 (dd, J = 4.0, 2.7Hz, 1H), 6.77-6.76 (m, 1H), 6.40-6.37 (dt, J = 3.7, 2.5 Hz, 1H).

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Ji-An; Zhang, Zhen-Yu; Gao, Jie; Tan, Jia-Hui; Gu, Xian-Feng; Tetrahedron Letters; (2019);,
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Synthetic Route of 796600-15-2, A common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, 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.

Examples 11 and 12Example 11 Example 12 11a to l ib(R)-2-(3 -chloro-4-cyano-2-methylphenylamino)-3 -hydroxypropanoic acidTo a stirred solution of 2-chloro-4-fluoro-3-methylbenzonitrile (1 la) (1.0 gm, 5.8 mmol) in DMSO (10 mL), D-Serine (1.4 gm, 13.3 mmol) was added followed by K2C03 (1.7 gm, 12.3 mmol) at room temperature. The resulting reaction mixture was heated to 90C for 12 h. After completion of reaction (by TLC), the reaction mixture was poured into ice-cold water (300 mL) and extracted with EtOAc (100 mL). The aqueous layer was acidified with citric acid (pH ~3) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over Na2S04, and concentrated under reduced pressure to afford the acid 1 lb (0.3 gm, crude) as off- white solid. The crude material was taken for the next step without purification.TLC: 10% MeOH/DCM (Rf: 0.2)1H NMR (500MHz, DMSO-c?, delta in ppm): 8.2-10.2 (br s, 1H), 7.54 (d, J= 8.5 Hz, 1H), 6.57 (d, J= 9.0 Hz, 1H), 5.79 (d, J= 7.5 Hz, 1H), 4.20 (t, J= 3.0 Hz, 1H), 3.86-3.79 (m, 2H), 3.22 (br s, 1H), 2.25 (s, 3H).

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; RADIUS HEALTH, INC.; MILLER, Chris, P.; WO2012/47617; (2012); A1;,
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Electric Literature of 16932-49-3, 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. 16932-49-3, name is 2,6-Dimethoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: :2,6-dimethoxybenzonitrile (501 mg, 3.07 mmol) and4-amino-7-chloroquinoline (548 mg, 3.07 mmol) were dissolved together in 20 mLof anhydrous tetrahydrofuran. The vesselwas swept with nitrogen and chilled in an ice-water bath. Ethereal 3.0 M ethyl magnesium bromide (2.05 mL,6.14 mmol) was added dropwise over 3 min.After briefly forming an off-white solid suspended in a yellow solution,within minutes the mixture became a dark amber homogenous solution with someoff-white solid material remaining. Thevessel was placed in a 75 C oil bath for 21 h before diluting with 60 mL ofwater. The pH was decreased to ca. 14 byaddition of 4 pellets of NaOH. Themixture was then extracted with 60 mL of ethyl acetate, using solid NaCl tofacilitate partitioning. The organicswere dried over MgSO4 and concentrated to 1.27 g of a crude brownoily paste containing mostly unreacted starting materials. Flash chromatography (150 mL silica gel, 50%ethyl acetate / hexane, then neat ethyl acetate, then 10% methanol in ethylacetate) returned 100 mg (9.6%) ofN-(7-chloroquinolin-4-yl)-2,6-dimethoxybenzimidamide (G).

The chemical industry reduces the impact on the environment during synthesis 2,6-Dimethoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Hershberger, Paul M.; Hedrick, Michael P.; Peddibhotla, Satyamaheshwar; Mangravita-Novo, Arianna; Gosalia, Palak; Li, Yujie; Gray, Wilson; Vicchiarelli, Michael; Smith, Layton H.; Chung, Thomas D.Y.; Thomas, James B.; Caron, Marc G.; Pinkerton, Anthony B.; Barak, Lawrence S.; Roth, Gregory P.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 262 – 267;,
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Related Products of 29509-06-6, The chemical industry reduces the impact on the environment during synthesis 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, I believe this compound will play a more active role in future production and life.

7-A. 5-Isopropyl-isoxazol-3-ylamine.; To a mixture of 4-methyl-3-oxopentanenitrile (11 g, 99 mmol) and water (200 mL) is added NaOH (4.95 g, 124 mmol). Once the NaOH pellets are completely dissolved, hydroxylamine sulfate (8.93 g, 109 mmol) is added and after 5 min the pH is measured (pH 7-8). The reaction is warmed to 40 0C and stirred for 72 h. At this point HCI (13.0 mL, 158 mmol, 37%) is added in one portion and the reaction warmed to 50 0C for 2.5 h. The reaction is removed from the oil bath and allowed to cool to rt. At this point a solution of NaOH (30% in H2O) is added to give a solution of pH 1 1. EtOAc is then added and the layers separated. The water layer is extracted with EtOAc (3 x) until no more product appears in the LCMS of the water layer. The combined organics are dried (Na2SO4) and evaporated to give 5-isopropyl- isoxazol-3-ylamine. MS (ESI) m/z 127.2 (M+1 ).

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, 4-Methyl-3-oxopentanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ARTMAN III, Gerald David; ELLIOTT, Jason Matthew; JI, Nan; LIU, Donglei; MA, Fupeng; MAINOLFI, Nello; MEREDITH, Erik; MIRANDA, Karl; POWERS, James J.; RAO, Chang; WO2010/66684; (2010); A2;,
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Electric Literature of 612-24-8,Some common heterocyclic compound, 612-24-8, name is 2-Nitrobenzonitrile, molecular formula is C7H4N2O2, 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 a suspension of a respective 2-nitro-benzonitrile 3a,b or 7a,b (15 mmol) in water (10 mL) was added sodium dithionite (60 mmol), and the reaction mixture was heated to 50C and stirred at this temperature for 3-4 h. Then, the temperature was raised to 65C and concentrated HCl (5 mL) was added dropwise in 30 min. The resulting mixture was cooled to 20C, and the pH was adjusted to ~10 using 50% aqueous sodium hydroxide solution. The formed precipitate was filtered, washed with cold water, n-hexane, and dried at 40oC to afford 2-nitro-benzonitriles 8a-d, respectively.

The synthetic route of 612-24-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Le-Nhat-Thuy, Giang; Dinh, Thuy Van; Pham-The, Hai; Nguyen Quang, Hung; Nguyen Thi, Nga; Dang Thi, Tuyet Anh; Hoang Thi, Phuong; Le Thi, Tu Anh; Nguyen, Ha Thanh; Nguyen Thanh, Phuong; Le Duc, Trung; Nguyen, Tuyen Van; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3741 – 3747;,
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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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3ClFN

a) (2S)-2-[(3-Chloro-4-cyanophenyl)amino]-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid2-Chloro-4-fluorobenzonitrile (2.13 g, 13.8 mmol), (2S)-2-amino-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid (2.6 g, 13.8 mmol) and NaHCO3 (3.5 g, 41.4 mmol) in DMSO (70 mL) and H2O (10 mL) were stirred at 95 C. for 15 h. After cooling, the reaction mixture was diluted with H2O (100 mL) and washed with Et2O (100 mL). The H2O layer was acidified to Congo Red midpoint and extracted with Et2O (2¡Á). The combined organic extracts were washed with H2O, dried over Na2SO4, filtered, and concentrated to give the titled product (3.59 g, 80%) as a foam. 1H-NMR (CDCl3) delta: 1.45 (9H, s), 2.89 (2H, m), 3.54 (1H, m), 4.42 (1H, m), 6.55 (1H, d, J=8.8 Hz), 6.70 (1H, s), 7.43 (1H, d, J=8.4 Hz). LC-MS (ES) m/e 325.4 (M+H)+.

According to the analysis of related databases, 60702-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WASHBURN, David G.; HOANG, Tram H.; US2008/39517; (2008); A1;,
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Reference of 134227-45-5, These common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, 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.

A mixture of 8-(pirhoeridin-3-ylacetyl)-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (0.035 g, 0.00012 mol), 3,4,5-trifiuorobenzonitrile (0.0209 g, 0.000133 mol) and potassium carbonate (0.0419 g, 0.000303 mol) in N,N-dimethylformamide (0.700 mL, 0.00904 mol) was heated at 100 0C overnight. After quenched with water, the mixture was extracted with EtOAc. The organic layers were combined, washed with water and brine successively, dried, and evaporated to dryness. The residue was purified on RP-HPLC to give the desired product (36 mg 77%). LCMS (M+H) 390.2. The product was believed to have a 3-endo configuation based on the starting materials.

Statistics shows that 3,4,5-Trifluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 134227-45-5.

Reference:
Patent; INCYTE CORPORATION; WO2007/89683; (2007); A1;,
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