Month: October 2020

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 103146-25-4 as follows. 103146-25-4

R-enriched cyanodiol (I) (lOg, 0.292 moles) prepared as per example 2 was dissolved in dichloromethane (40ml) at 20-40 C and cooled to 0-5C. Then triethylamine (4.4g; 0.043 moles) followed by a solution of benzoyl chloride (4.5g, 0.03 mole) in dichloromethane (10ml) was added at 0-5C. The reaction mass was maintained further at 0-5 C for 2 hours. After maintaining 10% sodium chloride solution was added and the resulting biphasic mixture was stirred at 10- 20 C for 10-20min. Then the organic layer was separated and concentrated under vacuum at 35-40C which afforded 13.2 g of mono benzoyl cyanodiol ester as an oil. To this obtained mono benzoyl cyanodiol ester, acetone (35ml) followed by a solution of oxalic acid dihydrate (3.6g, 0.03rnoles) in acetone (23ml) was added. Then the reaction mass was maintained at 30-40 C for 1-2 hours. After maintaining was over the reaction mass was cooled to 0-5C whereupon the precipitated solid was filtered, washed with acetone (12 ml) and dried under vacuum at 50-60C which afforded 6.0g title compound (lllf) as a white solid. 1H-NMR in CDC13 at 400MHz (ppm): 1.24-1.60 (d, 2H), 2.03-2.31 (d, 2H), 2.48 (s, 6H), 2.79-2.84 (dd, 2H), 4.73-4.77 (d, 1H), 5.27-5.31 (d, 2H), 6.66-7.67 (m, 12H- Aromatic) Mass Analysis (ESI, +ve mode): Molecular ion peak observed at 447.47 a.m.u which corresponds to the freebase of the title compound.

According to the analysis of related databases, 103146-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IPCA LABORATORIES LIMITED; REGURI, Buchi Reddy; PRASAD, Ashok; RAWAT, Ajay Singh; RAJPUT, Sandip; SANTAN, Rohit B; (36 pag.)WO2017/9866; (2017); A1;,
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1813-33-8, Adding a certain compound to certain chemical reactions, such as: 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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 1813-33-8.

General procedure: Appropriate ROH (3.00 mmol) was added topotassium tert-butoxide (3.00 mmol) solution in toluene (7 ml).1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 3ml)was added to the mixture and stirred for 30 min at 80 C. Aftercooled down to ambient temperature of the reaction mixture,2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) in toluenewas dropwise and stirred for 3 h at 80 C. The reaction wasquenched by adding water and extracted with EtOAc twice. Thecombined organic extracts were dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:7) eluantcondition.

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, 2-Chloro-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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60758-86-3, Adding a certain compound to certain chemical reactions, such as: 60758-86-3, name is 3-Ethoxy-4-methoxybenzonitrile, 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 60758-86-3.

Dimethylsulfone (191. Ig, 2.03 moles, from Aldrich Chemicals, Milwaukee, WI) and tetrahydrofuran (1.65 L, from Aldrich Chemicals, Milwaukee, WI) were charged to a 12 L three-necked flask at room temperature. The mixture was cooled to 0-5C. n-BuLi (750 ml of 2.5M solution in hexanes, from Aldrich Chemicals, Milwaukee, WI) was added to the flask at a rate such that the reaction mixture was maintained at 0-5C. A line rinse with 150 ml tetrahydrofuran followed. The mixture was stirred at 0-5C for 60-70 minutes. 3-ethoxy-4- methoxybenzonitrile (300.0 g, 1.69 moles, in 750 ml tetrahydrofuran) was then charged to the flask at a rate such that the reaction mixture was maintained at 0-5 C . A line rinse with 300 ml tetrahydrofuran followed. The mixture was stirred at 0-5C for another 10-15 minutes. After warming to room temperature, the reaction mixture was stirred at room temperature for 1.5-2 hours, while purged with nitrogen. NaBH4 (83.1 g, 2.20 moles, from Aldrich Chemicals, Milwaukee, WI) and 150 ml of tetrahydrofuran were then charged to the reaction mixture. The reaction mixture was stirred at 0-50C for 15-30 minutes. HOAc (450 ml, 7.83 moles, from Fisher Scientific, Pittsburgh, PA) was charged to the flask at a rate such that the reaction mixture was maintained at 0-50C. The mixture was stirred at 0-50C for an additional 2-3 hours. The mixture was then charged with 2.25 L of NaOH (2.5N, pH 12 to 13, from Fisher Scientific, Pittsburgh, PA), and stirred at 0-50C for another 15-30 minutes. After warming to room temperature, the reaction mixture was heated to reflux at about 600C. After reflux for 12-14 hours, the mixture was cooled to 35-40C, and 3.0 L of water was added. The mixture was further cooled to 0-5C over a period of 1.5-2 hours. The mixture was filtered under vacuum, and the filtered solid was washed with 2 L of deionized water. The solid was dried in a tray at 50-550C under vacuum. The yield of 2-(3-ethoxy-4-methoxyphenyl)-l-(methanesulfonyl)-eth- 2-ylamine was found to be 352 g (76.1%) based on a 300 g input of 3-ethoxy-4- methoxybenzonitrile (HPLC indicated 99.74% purity by peak area).

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-Ethoxy-4-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE CORPORATION; SAINDANE, Manohar, T.; GE, Chuansheng; WO2010/30345; (2010); A2;,
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67515-59-7, Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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 67515-59-7.

DESCRIPTION FOR D14-[(1-methylethyl)oxy]-3-(trifluoromethyl)benzonitrile (D1)To a solution of 4-fluoro-3-(trifluoromethyl)benzonitrile (10 g), i-PrOH (8.15 mL) in tetrahydrofuran (THF) (90 mL) stirred under nitrogen at -10 C. was added solid NaH (3.46 g) portionwise during 30 min. The reaction mixture was stirred at -10 C. for 6 h. The reaction mixture was quenched with water, partitioned between ether (100 mL) and water (50 mL). The organic phase was dried over magnesium sulphate and evaporated in vacuo to give the crude product 4-[(1-methylethyl)oxy]-3-(trifluoromethyl)benzonitrile (D10) (15 g).

According to the analysis of related databases, 67515-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; US2011/269738; (2011); A1;,
Nitrile – Wikipedia,
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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 6393-40-4 as follows. 6393-40-4

Step 1 A mixture of 4-amino-3-nitrobenzonitrile (63.3 g, 388 mmol) in 1,4-dioxane (600 mL) and anhydrous ethanol (600 mL) was cooled in an ice water bath to 0-5 C. and treated with gaseous HCl for 1.5 h. The reaction mixture was tightly sealed and allowed to warm up to room temperature with stirring for 18 h. The flask was then carefully unsealed and the reaction mixture was diluted with anhydrous diethyl ether (about 2.4 L) until a cloudy solution was obtained. A minimum amount of absolute ethanol required to give a clear solution was then added, and the resulting solution stirred until crystals of 4-amino-3-nitro-benzimidic acid ethyl ester were observed. Ether was then cautiously added to complete the crystallization process and the suspension was allowed to stand for about 30 minutes. The crystals were filtered and washed with dry diethyl ether, then allowed to dry under aspirator vacuum. The crystals were dried in vacuo to give 4-amino-3-nitro-benzimidic acid ethyl ester hydrochloride (84.6 g) as off-white crystals.

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS, INC.; Dickman, Daniel A.; Kumar, Dange Vijay; O’Bryan, Colin; Rai, Roopa; Shrader, William Dvorak; US2014/80879; (2014); A1;,
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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 solution of 5-amino-2-[(pyrrolidin-1-yl)methyl]benzoxazole (200 mg, 0.92 mmol) and diphenylcyanocarbonimidate (263 mg, 1.10 mmol) in isopropyl alcohol (3.5 mL) was stirred overnight at ambient temperature, the resulting white solid product, (Z)-phenyl /V- cyano-/V-(2-(pyrrolidin-1-ylmethyl)benzo[d]oxazol-5-yl)carbamimidate, was filtered and used directly for the next step (290 mg, 87%).

According to the analysis of related databases, Diphenyl N-cyanocarbonimidate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2008/83354; (2008); A1;,
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A common compound: 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 16588-02-6

General procedure: To solution of 1.97 mmol (1.2 eq.) of phenol 2-8, 12-13 in 3 ml dry DMSO was added 79 mg(1.2 eq.) powdered NaOH. The mixture was heated at 50C for 20 min and to the formed clearsolution 0.300 g (1.64 mmol, 1.0 eq.) of 1 was added. The reaction mixture was heated at 80C for 8h. After cooling 40 ml water was added and extracted with DCM. The organic phase was washedwith aq. NaHCO3 and water, dried over Na2SO4, filtered and evaporated in vacuo. The crudeproducts 14-20, 24-25 were purified by column chromatography (50 g silica-gel). After column theformed solid products were powdered, washed with 3 ml hot hexane and dried in vacuo.

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, 16588-02-6, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dobrikov, Georgi M.; Slavchev, Ivaylo; Nikolova, Ivanka; Stoyanova, Adelina; Nikolova, Nadya; Mukova, Lucia; Nikolova, Rosica; Shivachev, Boris; Galabov, Angel S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 19; (2017); p. 4540 – 4543;,
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658-99-1, Adding a certain compound to certain chemical reactions, such as: 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, 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 658-99-1.

Step A: Preparation of 4-(3,4-Difluorophenyl)-tetrahydro-2H- pyran-4-carbonitri Ie; [0705] A mixture 2-(3,4-difluorophenyl)acetonitrile (25.00 g, 163 mmol) and 2-bromoethyl ether (22.8 mL, 163 mmol) in ether was added dropwise through an addition funnel to a mixture of sodium 2-methylpropan-2-olate (39.2 g, 408 mmol) in DMF (163 mL) at 0C. The reaction was then allowed to warm to ambient temperature aetad stirred for 3 hours. The reaction mixture was quenched with 12N HCl, diluted with 400 mL of EtOAc, added to a separatory funnel, partitioned with NaHCO3 (saturated, aqueous), washed 2 times with 100 mL OfNaHCO3 (saturated, aqueous), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound which was used without further purification. MS (m/z) = 224 (M+H)+.

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, 2-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
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31643-49-9, A common heterocyclic compound, 31643-49-9, name is 4-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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: 4-nitrophthalonitrile (1) (2 g, 11.5 mmol) was dissolved in dry DMSO (20 mL) and 5-hexyn-1-ol (1.69 g, 11.5 mmol) added under a nitrogen atmosphere. After stirring for 10 min, finely ground anhydrous K2CO3 (2.16 g, 15.6 mmol) was added in portions over 2 h, with stirring. The reaction mixture was stirred at 40 C for 48 h under nitrogen. Then the mixture was poured into 400 mL of cold water. The precipitate was filtered off and washed with water, until the filtrate was neutral. Recrystalization from hexane and methanol gives the desired compound as a yellow crystalline powder. Yield: 1.74 g (60%).

The synthetic route of 31643-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bankole, Owolabi M.; Britton, Jonathan; Nyokong, Tebello; Polyhedron; vol. 88; (2015); p. 73 – 80;,
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3939-09-1, name is 2,4-Difluorobenzonitrile, 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. 3939-09-1

Example 3 1-(2,4-Diamino-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (Compound 3); 2,4-Difluorobenzonitrile (2.78 g, 1 eq), guanidine hydrochloride (7.15 g, 3.74 eq), and sodium hydride (3.6 g, 7.6 eq) are added to dimethylacetamide (50 mL) and the resulting mixture is stirred at 150 C. for overnight. Then the reaction mixture is poured into sat’d NaHCO3 aq. solution (300 mL), extracted by EtOAc (3¡Á200 mL). The combined organic layers is dried over Na2SO4, filtered, concentrated. The crude product is purified by flash chromatography to give 7-Fluoro-quinazolin-2,4-diamine (1 g, 28% yield). LC/MS m/z=179 [M+H]+.

Statistics shows that 3939-09-1 is playing an increasingly important role. we look forward to future research findings about 2,4-Difluorobenzonitrile.

Reference:
Patent; Huang, Kenneth He; Veal, James; Barta, Thomas; Smith, Emilie D.; Ma, Wei; Ommen, Andy; US2008/70935; (2008); A1;,
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