Month: June 2021

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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Fluoro-5-nitrobenzonitrile

EXAMPLE 7; 1-(4-{4-[Bis-4-fluoro-phenyl)-methyl]-piperazin-1-yl}-3-cyano-phenyl)-3-(3,5-dimethyl-isoxazol-4-yl)-urea; Step a: 2-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazin-1-yl}-5-nitro-benzonitrile; A mixture of 1-[bis(4-fluorophenyl)methyl]piperazine (5.0 g, 17.3 mmol), 2-fluoro-5-nitro-benzonitrile (2.88 g, 1.0 eq) and potassium carbonate (2.64 g, 1.1 eq) in DMF (50 mL) was stirred at 50 C. for 2 hours. The mixture was poured into water and the precipitate was filtered off and washed with water before to be solubilised in DCM. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford a reddish gum. This gum was sonicated in DCM/Hexanes (2/8) and then the precipitate was filtered off and washed with Hexanes. After high-vacuum drying, 2-{4-[bis-(4-fluoro-phenyl)-methyl]-piperazin-1-yl}-5-nitro-benzonitrile (5.8 g, 77% yield) was obtained as an ocre solid which will be used without further purification.LC/MS: r.t. 5.33 min, 435.3 [M+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; Nozulak, Joachim; Orain, David; Cotesta, Simona; US2009/99199; (2009); A1;,
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Synthetic Route of 623-03-0, 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. 623-03-0, name is 4-Chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Zn(OAc)2·2H2O (5.0 mol%) was transferred to a 100 mL autoclavereactor equipped with an overhead stirrer and an automatic temperature-control system. The appropriate benzene-1,2-diamine 1 (2 mmol), DMF (10.0 mmol), and PMHS (5.0 mmol)were successively introduced. The reactor was sealed, flushedthree times with N2 (10 atm), and heated to the required temperature with vigorous stirring (600 rpm). During the course ofthe reaction, an increase of pressure was observed, due to thegeneration of Me2NH and HCHO at 120 C.15 (For this reason, the protocol needs to be performed in a sealed high-pressurereactor.) When the reaction was complete, the autoclave wascooled to r.t., and the pressure generated during the reactionwas carefully released. Basic hydrolysis was then carried out atr.t. for 30 min to remove unreacted PMHS from the mixture.13aThe mixture was then extracted with EtOAc (3 × 20 mL). Thecombined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude products were further purified bycolumn chromatography [silica gel (100-200 mesh), PE-EtOAc(20:4 to 10:2)]. The spectroscopic data for the products wereconsistent with those reported in the literature.

The chemical industry reduces the impact on the environment during synthesis 4-Chlorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nale, Deepak B.; Bhanage, Bhalchandra M.; Synlett; vol. 26; 20; (2015); p. 2835 – 2842;,
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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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Preparation 15: 2-methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzamide; Step 1 : 4-bromo-2-methylbenzamide; To a solution of 4-Bromo-2-methylbenzonitrile (3.00 g, 15.3 mmol) in ethanol (9 mL) was added 10% aqueous potassium hydroxide (8.60 mL, 15.3 mmol). The reaction was heated to 8O0C for 16 h. The reaction was cooled to 40C and the precipitated solid was filtered and washed with water to give the title compound as a white solid (2.45 g, 75%). 1H NMR (500 MHz, DMSO-d6) delta ppm 7.71 (bs, 1 H), 7.40 (m, 3H), 7.26 (d, 1 H), 2.31 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 67832-11-5.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); 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. 874-97-5, name is 3-Cyanobenzyl alcohol, A new synthetic method of this compound is introduced below., name: 3-Cyanobenzyl alcohol

To an ice-cold solution of 3-hydroxymethyl benzonitrile (4.95 g, 37 mmol) in CH2C12 (47 mL) was added imidazole (5.1 g, 74 mmol), DMAP (0.45 g, 3.7 mmol), and TBSC1 (6. 2 g, 41 mmol), and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water, and the aqueous layer was extracted with CH2C12 (3 x 150 mL). The combined organics were washed with brine, dried (MGS04), filtered, and concentrated under reduced pressure to provide 3- (tert-butyldimethylsilyloxymethyl)-benzonitrile (9.1 g, 99%) as a clear oil :H NMR (300 MHz, CDC13) 8 7.51 (s, 1H), 7.42 (d, J = 6 Hz, 1H), 7.35-7. 28 (m, 1H), 4.75 (s, 2H), 0.94 (s, 9H), 0.11 (s, 6H).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/18557; (2005); A2;,
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Electric Literature of 1194-02-1, 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. 1194-02-1, name is 4-Fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 40% methylamine methanol solution (7.5 mL) was added to a methanol (2.5 mL) solution of 4-fluorobenzonitrile (2.00 g) and the mixture was heated under reflux for fifteen hours under nitrogen atmosphere. After the solvent was removed under reduced pressure, to the residue obtained was added water (15 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The oil obtained by removal of the solvent under reduced pressure was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 2 : 1) to obtain the titled compound (0.48 g) as crystals.

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

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; EP1391452; (2004); A1;,
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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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 654-70-6

To a nitrogen flushed, 30-L kettle was charged aniline E (4.0 kg, 21.49 mol) followed by w-heptane (9 L, 2.25 vol) and H20 (10 L, 2.5 vol). The mixture was then agitated for 8 min, cooled to 5-10 C and thiophosgene (1.81 L, 2.72 kg, 23.64 mol, 1.1 equiv) was charged over 12 min, maintaining the batch temperature at 10-16 C, followed by an w-heptane (1 L, 0.25 vol) rinse. The resulting orange slurry was then warmed to 30-40 C over 1.5 h and a slight exotherm to a maximum temperature of 46.4 C was observed. After stirring for 15 h, the orange solution was sampled (>99% conversion). The batch was then heated to 36 C and the phases were allowed to separate. A rag layer was observed and most of it was purged with the bottom aqueous layer. In two portions, w-heptane (18 L, 4.5 vol) was next charged to the orange heptane layer and the solution was distilled to 1.5 vol (45-46 C, 160 mbar). The solution was diluted once more with w-heptane (8 L, 2 vol) and the batch was distilled to 1.5 vol (45-46 C, 160 mbar). The solution was then diluted with w-heptane (10 L, 2.5 vol), cooled to 30-31 C (heptane:product F, 5.3:1) and seeded with product F (10 g). Crystallization was visible within 2-3 min after seeding and the slurry was further cooled to 0-10 C over 3 h and held at 0-10 C for 2 h. The batch was then filtered, rinsed with filtrate and cold w-heptane (4 L, 1 vol) and dried at 20-25 C, under vacuum, for 13 h to yield product F (4.51 kg, 92%), with an HPLC purity of >99%, and a moisture level of 0.04%.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott; WO2011/106570; (2011); 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 42872-74-2 as follows. SDS of cas: 42872-74-2

A mixture of ((R)-tetrahydrofuran-2-yl)(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-6-azaspiro[2.5]octan-6-yl)methanone (826 mg, 2.01 mmol), 3-bromo-4-methylbenzonitrile (394 mg, 2.09 mmol), bis (di-tert-butyl(4- dimethylaminophenyl) phosphine)dichloropalladium (142 mg, 0.20 mmol), potassium phosphate (852 mg, 4.02 mmol) and water (2 mL) in dioxane (10 mL) was stirred for 2 h at 90 C under nitrogen atmosphere. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with petroleum ether /ethyl acetate (1:1) to afford 6-methyl-4′-(6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)-[1,1′-biphenyl]-3-carbonitrile (636 mg, 80%) as a yellow solid. LCMS (ES, m/z): 401 [M+H]+.

According to the analysis of related databases, 42872-74-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forma Therapeutics, Inc.; Martin, Matthew W.; Zablocki, Mary-Margaret; Mente, Scot; Dinsmore, Christopher; Wang, Zhongguo; Zheng, Xiaozhang; (382 pag.)EP3636637; (2020); A1;,
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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. 151-18-8, name is 3-Aminopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

A. (S)-N-(2-Cyano-ethyl)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-Phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionamide. To a 3-neck round-bottom flask was added (S)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid (Example 1; 5.0 g, 9.9 mmol, 1.0 equiv), EDC (4.7 g, 24.7 mmol, 2.5 equiv) and HOBT (3.3 g, 24.7 mmol, 2.5 equiv) under nitrogen. N,N-Dimethylformamide (50 mL) was added, followed by 3-aminopropanenitrile (1.9 g, 24.7 mmol, 2.5 equiv) and diisopropylethylamine (6.8 mL, 39.6 mmol, 4.0 equiv). The reaction mixture was stirred overnight, then was diluted with ethyl acetate (200 mL), washed with 1 N HCl (100 mL), H2O (100 mL), 10% sodium bicarbonate (100 mL), H2O (100 mL) then brine (100 mL), and dried (sodium sulfate). The solvent was then removed under reduced pressure yielding the desired amide (5.35 g, 99%), which was used in the next step without purification. HPLC: Rt=7.89 (Method A). MS (ESI): mass calculated for C29H26Cl2N4O2, 532.14; m/z found, 533.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.31-7.30 (m, 2H), 7.23 (t, J=7.4 Hz, 1H), 7.19 (br s, 1H), 7.16-7.14 (m, 3H), 7.10 (d, J=7.4 Hz, 1H), 6.91 (dd, J=8.5, 2.2 Hz, 1H), 6.87 (d, J=9.0 Hz, 2H), 6.20 (s, 1H), 6.09 (t, J=6.0 Hz, 1H), 3.90 (dd, J=9.0, 6.0 Hz, 1H), 3.82 (s, 3H), 3.56-3.50 (m, 2H), 3.35-3.31 (m, 1H), 3.08 (dd, J=14.8, 6.0 Hz, 1H), 2.53-2.46 (m, 2H), 2.35 (s, 3H).

According to the analysis of related databases, 151-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); A1;,
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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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H3F4N

Synthesis of 3-(methylthio)-5-(trifluor e:[00376] In a 500-mL, 3 -neck round-bottomed flask equipped with an 100-mL pressure- equalizing addition funnel fitted with an nitrogen inlet, and a rubber septum, 3-fluoro-5- (trifluoromethyl)benzonitrile (8.0 g, 1.0 eq.), in acetone (40 mL). Sodiumthiomethoxide (3.42 g, 1.15 eq) was dissolved in water to make 21% aqueous solution and was added dropwise in 30 min at 5C temperature. The temperature of the reaction was slowly raised to RT and stirred for 3 h. Then temperature was raised to 50-60C and maintained for further 4-6 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH – dichloromethane as mobile phase and visualization with UV, SM Rf =0.40 and Product Rf = 0.25. Reaction was stirred for 3 hr at 25C and 4-6 hrs at 50-60C and reaction mixture was transparent. The reaction mass was quench by water and extracted by ethyl acetate (3×100 mL). The combined organic layer was washed with brine 50 mL and dried over sodium sulphate and evaporated on buchi rotaevaporator. The resulting crude compound (8 g) was subjected to further stage Yield (80.9 %); Mass: (ES+) 235.94 (M+l).

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; SHECHTER, Sharon; MCCAULEY, Dilara; WO2012/99807; (2012); A1;,
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These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, 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. Product Details of 77326-36-4

Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).

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

Reference:
Patent; SENOMYS, INC.; US2011/245353; (2011); A1;,
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