Month: July 2021

Electric Literature of 21803-75-8, These common heterocyclic compound, 21803-75-8, name is 4-Amino-3-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.

To 4-amino-3-chlorobenzonitrile (52 mg, 0.34 mmol), Cs 2CO 3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110 C. for 60 min in the microwave. Et 2O (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo.

The synthetic route of 21803-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENHWA BIOSCIENCES INCORPORATED; HADDACH, MUSTAPHA; TRAN, JOE A; PIERRE, FABRICE; REGAN, COLLIN F; RAFFAELE, NICHOLAS B; RAVULA, SUCHITRA; RYCKMAN, DAVID M; (482 pag.)JP5802676; (2015); B2;,
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Related Products of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A test tube equipped with a stopper was charged with 100 mg (0.292 m mol) of [ 4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL)-3-HYDROXYMETHYL-] benzonitrile, 50 mg of Novozym 435 (product [OF NOVOZYMES),] 333 mg (2.92 m mol) of vinyl butyrate, 0.292 m mol of various kinds of additives and 1 ml of toluene, and stirred at the temperature [OF 40C] for 16 hours. The results are shown in Table 3. Example 5 In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 1.5 g [(4.] [38] m mol) of [()-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.45 g of Novozym 435 (product [OF NOVOZYMES),] 0.347 g (4.38 m mol) of pyridine, 4.38 m mol of various kinds of acids and 1.00 g (8.76 m mol) of vinyl butyrate were added, and stirred at [40C] for between 16 and 21.5 hours. The result is shown in Table 4. Example 6 In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 3.0 g [(8.] 76 m mol) of [( : L)-4- [4-DIMETLIYLAMINO-L- (41-FLUOROPHENYL)-L-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.9 g of Novozym [435] (product [OF NOVOZYMES),] 0.693 g (8.76 m mol) of pyridine, 8.76 m mol of various kinds of acids and 2.00 g (17.52 m mol) of vinyl butyrate were added, and stirred at [40C] for between 15.5 and 16.5 hours. The results are shown in Table 5.

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-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
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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. 124289-21-0, name is 3-Bromo-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-methylbenzonitrile

a) Preparation of Compound 43B (0368) To a solution of 3-bromo-5-methylbenzonitrile (1.0 g, 5.12 mmol) in MeOH (40 mL) was added NiCl2.6H2O (121 mg, 0.51 mmol), Boc2O (1.35 g, 6.20 mmol) and NaBH4 (780 mg, 20.5 mmol) at -20 C. Then the mixture was stirred for 2 hrs at 0-10 C. The reaction solution was quenched with sat. NH4Cl (120 mL), diluted with H2O (200 mL) and extracted with EA (100 mL×3). The combined organic layers were washed by brine (50 mL×2), dried over Na2SO4 and concentrated to give tert-butyl 3-bromo-5-methylbenzylcarbamate (Compound 43B, 1.3 g, 86.7%) as a white solid. MS: calc’d 300 (M+H)+, measured 300 (M+H)+.

The synthetic route of 124289-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Hoves, Sabine; Wang, Lisha; Yun, Hongying; Zhang, Weixing; Zhu, Wei; (58 pag.)US2016/257653; (2016); A1;,
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Reference of 51762-67-5,Some common heterocyclic compound, 51762-67-5, name is 3-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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: A mixture of 3-nitrophthalonitrile (1.72 g, 0.01 mol), methyl hydroxybenzoate (0.01 mol), and potassium carbonate (13.90 g, 0.1 mol) in DMF (80 mL) was heated at 80 C overnight. Then the reaction mixture was poured into ice water. After filtration, the solid product was purified by silica-gel chromatography using CH2Cl2 as eluent to give a white solid product.

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

Reference:
Article; Bai, Ming; Zhang, Yan; Song, Rui; Han, Senjian; Wan, Peihong; Zhang, Chongxi; Dyes and Pigments; vol. 97; 3; (2013); p. 469 – 474;,
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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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 1835-65-0

Referential Example 1 Synthesis of 4,5-bis(2,5-dichlorophenoxy)-3,6-difluorophthalonitrile Into a separable flask of glass provided with a stirrer, a thermometer, a water separation tube, and a cooling tube and having an inner volume of 300 ml, 242.5 gr of acetone and 19.1 gr (0.0955 mol) of tetrafluorophthalonitrile were placed, to dissolve tetrafluorophthalonitrile in acetone homogeneously. Next, the resultant solution and 134 gr (0.2306 mol) of potassium fluoride were added together and the resultant reaction slurry was retained at -5° C. To this reaction slurry, 34.1 gr (0.2092 mol) of 2,5-dichlorophenol dissolved uniformly in 30.5 gr of acetone was added dropwise over a period of one hour. The reaction proceeding during the dropwise addition was continued with the reaction product cooled from the exterior so as to keep the interior temperature thereof in the range of -5° C. to 0° C. After the dropwise addition was completed, the reaction mixture was retained for additional two hours. After the reaction was completed, the contents of the flask were cooled to 20° C. and filtered to separate the solid component. The solid component was washed with 10 gr of acetone and the washed solid component and the filtrate were mixed together. The resultant filtrate was evaporated under a reduced pressure to expel acetone by distillation. The weight of the produced dry component was 45.8 gr (crude yield: 98.7 mol). This dry component was found to contain 42.9 gr of the target product, 4,5-bis(2,5-dichlorophenoxy)-3,6-difluorophthalonitrile (yield: 92.4 mol percent).

The synthetic route of 1835-65-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hirota, Kouichi; Hashimoto, Yukihide; Masuda, Kiyoshi; Kitao, Masunori; US2005/203293; (2005); A1;,
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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 67832-11-5 as follows. HPLC of Formula: C8H6BrN

Compound BB-2H-1 (11.50 g, 58.66 mmol) was dissolved in carbon tetrachloride (150 mL) at room temperature, followed by addition of N-bromobutanimide (31.32 g, 175.98 mmol) and benzoyl peroxide (1.42 g, 5.87 mmol). After completion of the addition, the reaction mixture was heated to 85 C and stirred for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, followed by filtration. The filter cake was wash with ethyl acetate (50 mL). The filtrate was combined and concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate (50 mL), washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, filtered to remove the desiccant, and concentrated under reduced pressure to obtain the title compound BB-2H-2 (pale-yellow solid, 20.00 g). The crude product was used directly in the next step without purification. 1H NMR (400MHz,CDCl3) delta: 8.18 (d, J = 1.8 Hz, 1H), 7.60 (dd, J = 1.8, 8.3 Hz, 1H), 7.48 (d, J = 8.3 Hz, 1H), 6.92 (s, 1H).

According to the analysis of related databases, 67832-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
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Application of 630-18-2,Some common heterocyclic compound, 630-18-2, name is Pivalonitrile, molecular formula is C5H9N, 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.

5) Example 1-5:Preparation of methyl trimethylacetimidate hydrochlorideTo a reactor were added 1.6 kg of trimethylacetonitrile and 1.48 kg of methanol andthe reactor was cooled to -10C. Acety 1 chloride in the amount of 1. 81 kg was slow 1 yadded thereto and the mixture was stirred at 0Cfor 12 hours. While stirring, theinternal temperature of the reactor was maintained at ooc. Upon termination of thereaction, the solvent was removed at 45C under reduced pressure. To the reactionmixture was added 11.8 kg of tert-butyl methyl ether and the mixture was stirred at oocfor 3 hours. The resulting solid was filtered and vacuum-dried at 40C to obtain 2.63kg of methyl trimethylacetimidate hydrochloride (yield: 90% ).1H-NMR (400MHz, DMSO-d6): 11.7(s, 2H), 4.07(s, 3H), l.O(s, 9H)

The synthetic route of 630-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CJ HEALTHCARE CORPORATION; KWEON, Jae Hong; KIM, Eun Sun; SONG, Seog Beom; LEE, Sung Ah; LEE, Ji Yun; CHOI, Kwang Do; PARK, Young Joon; WO2015/5615; (2015); A1;,
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Some common heterocyclic compound, 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, molecular formula is C6H7NO, 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. category: nitriles-buliding-blocks

To a 50 mL round-bottom flask containing 3-cyclopropyl-3-oxopropanenitrile 201 (1.63 g, 14.94 mmol, 1.0 equiv.), ethanol (20 mL), and TEA ( 1.51 g, 14.92 mmol, 1 .0 equiv.), N- hydroxybicyclo[2.2.2]oct-l-carbonimidoyl chloride 20h (2.8 g, 14.92 mmol, 1.0 equiv.) was added. The reaction mixture was stirred for 5 rain at 0 C and then for 2 h at RT. The resulting mixture was diluted with EtOAc (300 mL), washed with brine ( 100 mL x 2), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by Flash-Prep-HPLC using the following conditions: Column, silica gel; mobile phase, PE:EtOAc = 100:0 increasing to PE_EtOAc=80:20 within 30 min; Detector, UV 254 ran. Removal of solvents provided 3-[bicyclo[2.2.2]octan-l -yl]-5-cyclopropyl-l,2-oxazole-4-carbonitrile 20j (1.7 g, 47%) as a light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 118431-88-2, its application will become more common.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
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Synthetic Route of 78881-21-7, 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. 78881-21-7 name is 4-Amino-3-methylbenzonitrile, 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.

step 1-To a solution of 26a (1 mmol) in IPA was added 4-methyl-4-amino-benzonitrile (104, 1 mmol) then concentrated HCl (5 drops). The solution was stirred at 100 C. overnight. The reaction mixture was cooled and the resulting precipitate was filtered and washed thoroughly with IPA to afford 0.204 g (80%) of 106a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2008/146595; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 2032-34-0, name is 3,3-Diethoxypropanenitrile, 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 2032-34-0, Safety of 3,3-Diethoxypropanenitrile

To a stirred solution of 3,3-diethoxypropane-nitrile (1-iA, 283.80 g, 1.98 moles) and methyl formate (I- IB, 148.80 g, 2.48 moles) in anhydrous THF (1.1 L) at 10 C was added 1.0 M potassium tert-butoxide in THF (2.2 L. 2.2 moles). The temperature was maintained in the range of 10 C to 15 C throughout the 45 minute addition. Following the addition, the resulting slurry was stirred for 2 hours at ambient temperature. Hexane (400 niL) was then added and stirring was continued for another 20 min. The slurry was filtered and the cake washed with 1/1 hexanes/THF and dried overnight at 60 CC in a vacuum oven to provide I-1C.?H-NMR (CD3OD) was consistent with the desired structure.

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, 3,3-Diethoxypropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; AMMANN, Stephen; BACON, Elizabeth M.; BRIZGYS, Gediminas; CHIN, Elbert; CHOU, Chienhung; COTTELL, Jeromy J.; NDUKWE, Marilyn; TAYLOR, James G.; WRIGHT, Nathan E.; YANG, Zheng-Yu; ZIPFEL, Sheila M.; (138 pag.)WO2020/36979; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts