Month: March 2021

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. 915394-29-5, name is 2-(3-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(3-Aminophenyl)-2-methylpropanenitrile

3-((7H-pyrrolor2,3-dlpyrimidin-4-yl)oxy)-N-(3-(2-cyanopropan-2-yl)phenyl)-4- methylbenzamide (1-11): To a solution of 4-methyl-3-((7-((2-(trimethylsilyl)ethoxy)methyl)- 7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)benzoic acid (200 mg, 0.5 mmol), HATU (230 mg, 0.6 mmol), DMAP (73 mg, 0.6 mmol) and iPr2NEt (220 uL, 1.25 mmol) in CH2C12 (3 mL) was added 2-(3-aminophenyl)-2-methylpropanenitrile (80 mg, 0.5 mmol) and the resulting mixture was stirred at room temperature for 24 hours. The solution was filtered to remove solids, concentrated and purified with column chromatography (dichloromethane : methanol = 10: 1) to afford 455 mg of product as a colorless oil. To the solution of the obtained oil in CH2CI2 (5 mL) was added TFA (0.5 mL) and the resulting mixture was stirred at room temperature for 5 hours. The solution was concentrated and dried with vacuum, then dissolved in THF (4 mL) and 1 N NaOH solution (4 mL). The reaction mixture was stirred for 24 h and extracted with ethyl acetate. The combined organic phase was washed with brine and dried with Na2S04, then filtered and concentrated, and purified by reverse phase HPLC to give 185 mg (90%) of title compound as a white solid.

According to the analysis of related databases, 915394-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; TREON, Steven, P.; BUHRLAGE, Sara, Jean; GRAY, Nathanael; TAN, Li; YANG, Guang; WO2015/89479; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, 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 3672-47-7, Application In Synthesis of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

2. Synthesis of Intermediate 2:Sodium hydroxide (1.76 g, 44 mmol)Was dissolved in 140 mL of 80% aqueous ethanol,1 (7 g, 40 mmol) was added to the reaction flask,N, N-diethylchloroacetamide (5.98 g, 40 mmol),Sodium iodide (14.99 g, 100 mmol).Room temperature reaction for 12 hours.The solvent was distilled off under reduced pressure,To the residue was added 100 mL of saturated brine and 200 mL of ethyl acetate,After thorough mixing,Separate the organic layer,Dried over anhydrous sodium sulfate,Concentrated, column chromatography,To give product 2 (7.72 g, 67%) as a red oil.

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:
Patent; Xiamen University Affiliated Zhongshan Hospital; Su Xinhui; Wang Liangliang; Li Yesen; Guo Zhide; Zhang Xianzhong; Chen Lichun; (18 pag.)CN106749279; (2017); A;,
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Reference of 52798-01-3, These common heterocyclic compound, 52798-01-3, name is Methyl (4-cyanophenyl)acetate, 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.

Methyl 2-(4-cyanophenyl)acetate (200 mg, 1.14 mmol), methanol (2 mL), Pd/C (a small amount) and 2 drops of concentrated hydrochloric acid were added in a 25 mL single-neck flask with a hydrogen balloon equipped, and the mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. After completion of the reaction according to TLC, the mixture was filtered and the filtrate was concentrated to afford a product methyl 2-(4-(aminomethyl)phenyl)acetate (white solid, 178 mg), with a yield of 74.2%. 1H NMR (400 MHz, DMSO) delta 8.22 (s, 2H), 7.44 (d, J = 8.1 Hz, 2H), 7.30 (d, J = 8.1 Hz, 2H), 3.98 (s, 2H), 3.71 (s, 2H), 3.61 (s, 3H). MS (ESI) m/z: 180.1 (M+1).

Statistics shows that Methyl (4-cyanophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 52798-01-3.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); 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. 143879-77-0, name is 2,6-Difluoro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2,6-Difluoro-3-nitrobenzonitrile

6-Fluoro-3-nitro-2-phenylaminobenzonitrile LiHMDS (1.0M in THF, 38 mL, 38.0 mmol) was added dropwise to a stirred solution of aniline (1.86 g, 19.9 mmol) in anhydrous THF (30 mL) under a nitrogen atmosphere at -78 C. After 10 min stirring at -78 C., a solution of 2,6-difluoro-3-nitrobenzonitrile (3.5 g, 19.0 mmol) in THF (15 mL) was added and stirring at -78 C. continued for 30 min. The crude mixture was quenched with water and diluted with EtOAc. The resulting emulsion was filtered through a pad of Celite and the organic fraction separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-100% EtOAc in cyclohexane) to afford the title compound (2.7 g, 55%). 1H NMR (CDCl3, 400 MHz): delta 9.94 (1H, br s), 8.51 (1H, dd, J=9.50, 5.88 Hz), 7.51-7.21 (5H, m), 6.68 (1H, dd, J=9.50, 7.46 Hz).

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 143879-77-0.

Reference:
Patent; Heald, Robert; Price, Stephen; Safina, Brian; Savy, Pascal Pierre Alexandre; Seward, Eileen Mary; Sutherlin, Daniel P.; Waszkowycz, Bohdan; US2012/202785; (2012); A1;,
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Related Products of 796600-15-2, 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 796600-15-2 as follows.

Example 1tra/?s-2-Chloro-4-[ [2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile, Isomer 2bsoluteIn a glass pressure vessel, a mixture of trans-2-amino-l-methyl-cyclopentanol (8.75 g, 53 mmol, 1.5 eq), 2-chloro-4-fluoro-3-methyl-benzonitrile (6 g, 35.4 mmol) and lithium carbonate (7.84 g, 106 mmol) in DMSO (72 mL) and water (7.2 mL) is degassed for 15 min by bubbling nitrogen through the mixture. The vessel is sealed and heated at 130 C for 36 h. After cooling to room temperature, the mixture is quenched over ice/water (700 mL) at 5 C (internal temperature) with stirring. After 15 min, the initially sticky solid turns into a cream solid that is collected by filtration and washed with cold water. The solid is stirred over EtOAc (100 mL) for 30 min and filtered through a pad of diatomaceous earth. The EtOAc filtrate is concentrated to afford 15 g of a yellow solid. The material is purified by silica gel chromatography using dichloromethane to elute impurities and 10%EtOAc/dichloromethane to elute final product to obtain the racemic title compound (9.2 g, 98%). 1H NMR (400 MHz, DMSO-d6) delta 7.48 (d, 1H), 6.90 (d, 1H), 5.51 (d, 1H), 4.66 (s, 1H), 3.65-3.74 (m, 1H), 2.21 (s, 3H), 2.01-2.13 (m, 1H), 1.50-1.78 (m, 5H), 1.07 (s, 3H). LC-ES/MS m/z (35C1/37C1) 265.2/267.1 (M+l). The compound is dissolved in MeOH (70 mL). The enantiomers are separated in 21 mg injections by supercritical fluid chromatography on two CHIRALPAK AD-H columns (2 x 25 cm, 5 muiotaeta) stringed in series. Mobile phase: 20% isopropanol/carbon dioxide. Flow rate: 65 mL/min. Detection: 215 nm. Each run is 6.48 min. The first eluting peak is obtained as Isomer 1 and the second eluting peak is obtained as the title compound, Isomer 2 (4.13 g, 100% enantiomeric excess). The enantiomeric excess is determined by SFC on a CHIRALPAK AD-H (4.6 x 100 mm, 5 muiotaeta) column using 20% isopropanol/carbon dioxide. Flow rate: 2.5 mL/min. Detection: 215 nm. Isomer 1 TR = 2.53 min. Isomer 2 (title compound) TR = 3.06 min.The compound of Example 1 can also be named or referred to as 2-chloro-4- [ [( 1 R,2R)-2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile.

According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (2013); A1;,
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Related Products of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: tert-butyl 3 -( 1 -cyanocyclobutyl)-3 -hydroxypyrrolidine- 1 -carboxylate[619] To a solution of cyclobutanecarbonitrile (1.75 g, 21.5 mmol) in THF (15mL) was added 2.0M lithium diisopropylamide (11 mL, 22.5 mmol) dropwise and the solution was stirred at -78 C for 45 minutes. Then a solution of tert-butyl 3-oxopyrrolidine-l- carboxylate (4.0 g, 21.5 mmol) in THF (2 mL) was added to the solution and the mixture was stirred at -78 C for 2 hours. The reaction mixture was quenched with saturated NH4C1 solution and extracted with EtOAc (25 mL x 3). The organic phase was washed with brine (20 mL), dried over Na2S04, filtered, and concentrated. The residue was purified by column chromatography eluted with petroleum ether: EtOAc = 2: 1 to obtain the title compound (0.9 g, 38.2 % yield) as a white solid. XH NMR: (400 MHz, CDC13): ? 3.64-3.40 (m, 4H), 2.44 (t, J= 7.8 Hz, 2H), 2.33-2.23 (m, 2H), 2.13-1.88 (m, 4H), 1.47(s, 9H)

The synthetic route of Cyclobutanecarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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Synthetic Route of 6575-00-4,Some common heterocyclic compound, 6575-00-4, name is 3,5-Dichlorobenzonitrile, molecular formula is C7H3Cl2N, 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.

3,5-Dichlorobenzonitrile (52.93 g, 307.7 mmol) was dissolved in anhydrous DMF (300 ml.) and cooled to 0 0C in an ice bath. Sodium methoxide (18.28 g, 338.5 mmol) was added as a solid and the mixture stirred from 0 0C to RT overnight. The reaction mixture was poured onto a slurry of 10% HCI and ice. The resultant solid was filtered off, washed with water, and dried overnight. This material was dissolved in a mixture of EtOAc and DCM, filtered to remove insoluble material, washed with water, dried over magnesium sulfate, filtered and concentrated to afford the title compound (46.48 g, 90%). 1H NMR (400 MHz, CDCI3) delta ppm 7.20 (t, 1 H), 7.10 (t, 1 H), 7.03 (dd, 1 H), 3.82 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichlorobenzonitrile, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157330; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 222978-02-1, name is 2-Fluoro-4-(hydroxymethyl)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 222978-02-1, category: nitriles-buliding-blocks

Step D Preparation of 4-Bromomethyl-2-fluoro-benzonitrile N-Bromosuccinimide (6.6 g, 0.037 mol) was dissolved in CH2Cl2 (150 mL), cooled to 0 C. and treated with dimethylsulfide (3.27 mL, 0.0446 mol). The solution was cooled to -20 C. and then treated dropwise with a solution of 2-fluoro-4-hydroxymethylbenzonitrile (3.74 g, 0.0248 mol) in CH2Cl2 (30 mL). After the addition, the reaction mixture was stirred at 0 C. for 2 h then left to warm to ambient temperature overnight. The reaction mixture was added to ice/H2O, extracted with EtOAc, the organic layer separated, washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound which was purified chromatography (silica gel, 5-10% EtOAc/hexane. 1H NMR (CDCl3) d 7.61 (dd, 1H, J=8, 8 Hz), 7.26-7.30 (m, 2H), 4.45 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-4-(hydroxymethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US6297239; (2001); B1;,
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Application of 105-34-0, 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. 105-34-0, name is Methyl 2-cyanoacetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of aromatic aldehyde (10 mmol) and active methylene compound(10 mmol) in 10 mL ethanol was introduced in a 20 mL heavy walled pearshapedtwo-necked flask with nonstandard taper outer joint. The flask wasattached to a 12 mm tip diameter probe and the reaction mixture wassonicated at ambient temperature for the specified period at 50% power of theprocessor and 230W output in a 4 s pulse mode. At the end of the reactionperiod, TLC was checked and the flask was detached from the probe and thecontent was transferred into a beaker. The formed solid was filtered off andwashed thoroughly with cold ethanol (2 10 ml) to afford the Knoevenageladduct 3.

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, Methyl 2-cyanoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dandia, Anshu; Jain, Anuj K.; Laxkar, Ashok K.; Bhati, Dharmendra S.; Tetrahedron Letters; vol. 54; 24; (2013); p. 3180 – 3184;,
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Related Products of 97165-77-0,Some common heterocyclic compound, 97165-77-0, name is 3,5-Dibromobenzonitrile, molecular formula is C7H3Br2N, 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 79 3-(2′-amino-1^2,2-trimethyl-5′-oxo-r,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-5- bromobenzonitrileA resealable glass pressure tube was charged with 2′-amino-l’,2,2-trimethyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)spiro[chroman-4,4′-imidazol]-5′(rH)-one (50 mg, 0.13 mmol), 3,5-dibromobenzonitrile (34 mg, 0.13 mmol), dichloro[l, -bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (5.3 mg, 0.0065 mmol), 20% aqueous Na2C03 (241 mu., 0.45 mmol), and 1 ,4-dioxane (1.3 mL, 0.13 mmol). The reaction mixture was sparged with N? for 5 minutes, capped, stirred at 90C for 2 hours and allowed to cool to room temperature. The mixture was then diluted with EtOAc ( 10 mL) and washed with water (2 mL). The organic layer was separated, dried (MgS04), filtered and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (Biotage Flash 40S+) eluting with 5% MeOH/DCM. The product isolated was triturated with EtOAc. The solid formed was filtered, washed with additional EtOAc (2 X 1 mL) to provide 3-(2′-amino-r,2,2-trimethyI-5′-oxo- ,5′- dihydrospiro[chroman-4,4′-imidazole]-6-yl)-5-bromobenzonitrile ( 12 mg, 21% yield) as a solid. ‘H NMR (400 MHz, (CD3)2SO) delta 8.05 (s, 1H), 7.97 (s, 2H), 7.54 (d, J=7.04Hsz, 1H), 6.99 (s, 1 H), 6.88 (d,J=8.61Hz, 1H), 6.52 (br s, 2H), 3.05 (s, 3H), 2.19 (d, J=14.08 Hz, 1H), 1.82 (d, J=14.08 Hz, 1H), 1.43 (s, 3H), 1.39 (s, 3); LCMS (APCI+) m/z 439, 442 (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 3,5-Dibromobenzonitrile, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Nitrile – Wikipedia,
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