Tag: M.W=100-200

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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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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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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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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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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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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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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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. 21423-84-7, name is 2-Chloro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-4-methylbenzonitrile

4-(Bromomethyl)-2-chlorobenzonitrile (Intermediate h) [00161] To a solution of 44 (160 mg, 1.05 mmol) in CCLI (5 mL) was added NBS (224 mg, 1.26 mmol), AIBN (183 mg, 1.05 mmol). The mixture was stirred at 70 C for 6 h. The mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (petroleum ether / ethyl acetate = 10:1) to give intermediate h (110 mg, 45%) as a white solid.

According to the analysis of related databases, 21423-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); 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. 591769-05-0, name is 3-Cyclopentylacrylonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Cyclopentylacrylonitrile

To a solution of 4-(1H-pyrazol- 4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (15.0 g, 0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cis and trans isomers), followed by DBU (15 mL, 0.10 mol). The resulting mixture was stirred at room temperature overnight. The ACN was evaporated. The mixture was diluted with ethyl acetate, and the solution was washed with 1.0 N HCl. The aqueous layer was back-extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient of ethyl acetate/hexanes) to yield a viscous clear syrup, which was dissolved in ethanol and evaporated several times to remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H column, 15percent ethanol/hexanes) and used separately in the next step to generate their corresponding final product. The final products (see Step 3) stemming from each of the separated enantiomers were found to be active JAK inhibitors; however, the final product stemming from the second peak to elute from the preparative-HPLC was more active than its enantiomer. The products may be isolated by preparative HPLC or other means known to those of skill in the art for use in Step 3 below. 1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H), 8.32 (s, 2H), 7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H), 3.54 (t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H), 2.03- 1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H),?0.06 (s, 9H); MS(ES): 437 (M+1).

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; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (637 pag.)WO2015/193740; (2015); A2;,
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These common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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. HPLC of Formula: C9H6F3N

In a first Schlenk vessel 2,5-difluoro-1,4-benzenedicarbaldehyde 1 (680 mg, 0.40 mmol) and (4-trifluoromethyl)phenylacetonitrile 2 (1.48 g, 0.80 mmol) were taken in absolute ethanol (50 mL). In a second Schlenk vessel, sodium ethoxide (0.400 g, 5.76 mmol) and freshly distilled dry pyridine (4.96 mmol, 0.40 mL) were taken in absolute ethanol (50 mL). Under protection from air, the two solutions were mixed and heated to reflux for 3 h.;Then, pyridine and volatiles were removed under reduced pressure. Under protection from air, the residue was repeatedly extracted with small portions (15 mL) of dichloromethane. The organic layer was washed with water, dried over anhydrous MgSO4, and then, filtered through a syringe filter. The extract was evaporated under reduced pressure to leave the residue affording 2,5-difluoro-1,4-phenylene-3,3′-bis{2-[(4-trifluoromethyl)phenyl]acrylonitrile} 3 in 90% yield. Pale-green solid, M.p: 259-261 C; 1H NMR (400 MHz, CDCl3) 7.76 (d, phenyl, 4 H, J = 8.2 Hz), 7.83 (s, 2 H, ethenyl-H), 7.85 (d, 4 H, phenyl, J = 8.2 Hz), 8.21 (t, 2H, phenyl, J = 8.4 Hz). EI-MS (MH+): 503. Elemental analysis calculated for C26H12F8N2: C, 61.91%; H, 2.40%; N, 5.55%. Found: C, 61.80%; H, 2.55%; N, 5.64%.

The synthetic route of 4-(Trifluoromethyl)phenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moriguchi, Tetsuji; Kitou, Naoya; Jalli, Venkataprasad; Yoza, Kenji; Nagamatsu, Shuichi; Okauchi, Tatsuo; Tsuge, Akihiko; Takashima, Wataru; Journal of Molecular Structure; vol. 1118; (2016); p. 372 – 377;,
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