Tag: M.W=200-300

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 1141894-75-8 as follows. Application In Synthesis of 4-(Aminomethyl)-3-(trifluoromethyl)benzonitrile

General procedure: Biotransformations were performed in vitro using CoA ligases (phi, PhCL, CBL and ipfF) in combination with N-acyltransferases (CASHT and HolE) as purified proteins. The enzyme activity was evaluated towards a small panel of acids and amines (figure 2 & 6). Reactions were prepared in 1.5 ml Eppendorf tubes according to table 9 and incubated overnight at 21 C with shaking 700 rpm in an Eppendorf thermomixer. Reactions containing no N-acyltransferase served as a negative control. A summary of the reactions evaluated is presented in table 10, the associated LC-MS traces for successful reactions which yielded amide product are shown in figure 9. There was a background chemical reaction between the CoA ester corresponding to acid 7 with amines 23, 30 and 32, which was observed in the negative control. There was no detectable increase over the background in the corresponding N-acyltransferase (HolE) reactions; therefore amines 23, 30 and 32 are not substrates for HolE. Nonetheless, sixteen of the reactions screened were successful and yielded structurally diverse amide products in good yields.

According to the analysis of related databases, 1141894-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; LOVELOCK, Sarah, Louise; (66 pag.)WO2018/29097; (2018); A1;,
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Some common heterocyclic compound, 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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: 49674-15-9

Example 96 -(2,4-dimethoxypyrimidin-5-yl)-4-((3-((4-fluorophenyl)amino)-5-(2H-tetrazol-5- yl)phenyl)amino)quinoline-3-sulfonamide 3-((4-fluorophenyl)amino)-5-nitrobenzonitrile. To a suspension of 3-bromo-5- nitrobenzonitrile (500 mg, 2.202 mmol), 4-fluoroaniline (245 mg, 2.202 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1 ,1 ‘-biphenyl]-2-yl)phosphine (105 mg, 0.220 mmol) and cesium carbonate (1076 mg, 3.30 mmol) in ferf-butanol (2 ml.) and toluene (10 ml.) was added palladium(ll) acetate (9.89 mg, 0.044 mmol). The mixture was heated in a microwave synthesiser at 120 C for one hour. After cooling, the reaction was filtered and organic solvent was removed under reduced pressure. The resulting brown oil was purified by flash chromatography (silica gel, 0-100% ethyl acetate in hexanes) to afford 3-((4-fluorophenyl)amino)-5- nitrobenzonitrile (355 mg, 1.380 mmol, 62.7 % yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.19 – 7.30 (m, 4 H) 7.60 (dd, J=2.27, 1.26 Hz, 1 H) 7.89 (t, J=2.15 Hz, 1 H) 7.94 – 7.99 (m, 1 H) 9.06 (s, 1 H). LCMS (ES+) m/e 258 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 49674-15-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
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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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 36282-26-5

10235] Thetitle compound of Example 1 (9.8g, 55.3 mmol) and 2-bromo-4-fluorobenzonitrile (13.27 g, 66.4 mmol) are dissolved in anhydrous dimethylformamide (DMF, 300 mL). To this is added sodium hydride (95%, 2.79 g, 111 mmol) and the reaction is stirred at 550 C. for 1 hour. The reaction mixture is cooled to room temperature and water is added. A tan solid precipitated which is filtered, washed with water and ether and then dried in vacuo.

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; Hall, Steven E.; (44 pag.)US2015/329493; (2015); A1;,
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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. 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, A new synthetic method of this compound is introduced below., name: 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

To a 100 mL flask2,4-Bis (alpha,alpha -dimethylbenzyl) -2-yloxy) -3,5,6-trichloro-phthalonitrile (1 g), 3,4,5,6-Tetrachlorophthalonitrile 1,8-Diazabicycloundec-7-ene (0.8 g), 1-pentanol (7 g) and zinc acetate (0.2 g) were added and stirred while heating to 140 ° C. After completion of the reaction, the mixture is concentrated and purified by column chromatography.The liquid obtained after purification is concentrated to obtain a solid. The crystallized solid is vacuum-dried to obtain a compound represented by the following formula (6).

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; Samsung SDI Co., Ltd; Jeong Ui-su; Seo Hye-won; Shin Myeong-yeop; Han Gyu-seok; (40 pag.)KR2019/13136; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 185836-35-5, name is 4-(Benzyloxy)-2-fluorobenzonitrile, 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 185836-35-5, Quality Control of 4-(Benzyloxy)-2-fluorobenzonitrile

(B) 4-(Benzyloxy)-2-(methylsulfanyl)benzonitrile To a mixture of 4-(benzyloxy)-2-fluorobenzonitrile (500 mg) and DMF (10 mL), sodium methanethiolate (325 mg) was added at room temperature, and then the reaction mixture was stirred at the same temperature overnight. The reaction mixture was added to saturated aqueous ammonium chloride solution at room temperature and then extracted with ethyl acetate. The extract was washed with water and brine and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (442 mg). MS: [M+H]+ 255.9.

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-(Benzyloxy)-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OKANIWA, Masanori; BANNO, Hiroshi; HIRAYAMA, Takaharu; CARY, Douglas Robert; ONO, Koji; IWAMURA, Naoki; (99 pag.)EP3133075; (2017); A1;,
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Application of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Example 256A 5-Bromo-1H-indazol-3-ylamine The desired product was prepared by substituting 5-bromo-2-fluorobenzonitrile for 5-bromo-2-fluorobenzaldehyde in Example 35A.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
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These common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-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. COA of Formula: C7H3BrClN

Preparation of Intermediate 4-Bromo-2-chloro-benzaldehvde (l-3a):The 4-Bromo-2-chloro-benzaldehyde was prepared using procedures described in J. Med. Chem. 1981, 24, 1155-1161.4-bromo-2-chloro-benzonitrile (7.05g, 32.5 mmol) was dissolved in toluene (60 mL) and dichloromethane (1OmL) and cooled to -600C as a 1.5M solution of diisobutylaluminum hydride in toluene (33.4 ml, 49.8 mmol) was added dropwise over 30 minutes keeping the temperature between -60 and – 500C. The reaction was allowed to warm slowly to room temperature and stirred for an additional 3 hours. The reaction was quenched using ethyl acetate and stirred for 20 minutes before the addition of 1 N hydrochloric acid at O0C. The reaction was then allowed to warm slowly to room temperature. The reaction was extracted using ethyl acetate (2 times). Removal of the solvent provided the title compound (l-3a). 1H NMR (CDCI3): delta 7.52 (dd, 1H), 7.64 (d, 1H), 7.77 (d, 1H), 10.4 (s, 1 H)

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/59335; (2008); A1;,
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Related Products of 499983-13-0, 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 499983-13-0 as follows.

Ethylene carbonate (370.2 g, 4.204 mol, 30.0 eq.) was loaded in a 500 ml reactor at room temperature and heated to an internal temperature of 40C till all the solid melted. Then 1.4 g of PEG-200 (0.007 mol, 0.05 eq.) and 30.0 g of 4-bromo-3-fluorophenylacetonitrile (0.140 mol, 1.0 eq.) were charged in the reactor. Potassium tert-butoxide (31.4 g, 0.280 mol, 2.0 eq.) was added portion-wise, under stirring, to the resulting clear colorless solution. The internal temperature rose up to 60C. Then, the mixture was heated to 130C and kept under stirring for 8 hours. The mixture was cooled to 40C and then 105 g of toluene and 240 g of deionised water were added. The mixture was kept under stirring for 15 minutes at 40C and then stirring was stopped. After 15 minutes two layers were separated: a lower organic clear red phase and an upper aqueous colorless phase. The organic solution was reloaded into the reactor and heated to an internal temperature of 40C. 240 g of deionised water were added. The mixture was kept under stirring for 15 minutes at 40C and then stirring was stopped. After 30 minutes the yellowish opalescent aqueous layer (lower) was discarded and the organic phase was washed again two times with 240 g of deionised water. After 30 minutes, the yellowish opalescent aqueous layer was discarded. The organic solution was warmed to 80C and the volatile solvents were removed under reduced pressure until 36 ml as the final volume. A solution 9.6 g of isopropyl alcohol was added. The solution was cooled from 80C to 50C in 30 minutes and a small amount of seed was added. The crystallization mixture was cooled from 50C to 0C in 60 minutes. The suspension was stirred for at least 60 minutes then filtered washing three times with 9.0 g of a toluene/isopropyl alcohol mixture (1/1.25 w/w). The wet product was dried under vacuum at 40C for 15-18 hours. 22.7 g of a pale yellow solid were obtained (purity = 99,94%; molar yield = 68%).

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; ZaCh System S.p.A.; Verzini, Massimo; Cotarca, Livius; Guidi, Alberto; Melloni, Alfonso; Maragni, Paolo; EP2818460; (2014); A1;,
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Synthetic Route of 1210906-15-2, The chemical industry reduces the impact on the environment during synthesis 1210906-15-2, name is 5-Bromo-2-(trifluoromethoxy)benzonitrile, I believe this compound will play a more active role in future production and life.

Step 1A: 5-[(3R)-3-methylpiperazin-l-yll-2-(trifluoromethoxy)benzonitrile (0188) To a solution of tert-butyl (2R)-2-methylpiperazine-l-carboxylate (5.0 g, 25 mmol, 1.0 eq) and 5-bromo-2-(trifluoromethoxy)benzonitrile (3.8 mL, 25 mmol, 1 eq) in toluene (100 mL) was added sodium tert-butoxide (7.2 g, 75 mmol, 3.0 eq), racemic 2,2′-bis(diphenylphosphino)-l,l’-binaphthyl (1.6 g, 2.5 mmol, 0.10 eq), and lastly tris(dibenzylideneacetone)dipalladium(0) (2.3 g, 2.5 mmol, 0.10 eq), and the reaction mixture heated to 100 C overnight. The resulting dark reaction mixture was cooled, passed thru a pad of celite, and concentrated in vacuo. Silica gel column (80 g) was dry loaded and run using an increasing gradient of EtOAc (0-50%) in hexanes over 25 min. The chromatographed material was dissolved in dioxane (40 mL) and treated with a solution of 4M HC1 in dioxane (10 mL). The resulting thick suspension was concentrated, dissolved in MeOH, and made basic with the addition of MP-carbonate. Following removal of the resin and concentration of the filtrate, the free base of 5- [(3R)-3-methylpiperazin-l-yl]-2-(trifluoromethoxy)benzonitrile la (5.2 g, 18 mmol, 72% over two steps) was isolated as an orange oil.

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, 5-Bromo-2-(trifluoromethoxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
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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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-5-fluorobenzonitrile

Step 1 (0915) A solution of 3-bromo-5-fluorobenzonitrile (CXVIII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CXIX) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

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; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (390 pag.)US2016/90380; (2016); A1;,
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