Tag: M.W=100-200

These common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, 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 3672-47-7

In a 15 mL reaction tube, add 1c (52.6 mg, 0.3 mmol), 1,2-dichloroethane (DCE, 1 mL), 2-methyl-4-phenyl-3-butyn-2-ol (2a , 72.1mg, 0.45mmol),Dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer ([RhCp * Cl2] 2, 13.0mg, 0.021mmol) and CsOAc (57.6mg, 0.3mmol) will react in the air atmosphere The tube was sealed and the reaction was stirred at 100 C for 24 h. After the reaction was completed, the reaction tube was cooled to room temperature, suction filtered, and the mother liquor was spin-dried with silica gel and separated through a silica gel column (petroleum ether / ethyl acetate = 10/1) to obtain 3c (61.8 mg, 65%) as a yellow solid.

The synthetic route of 3-(4-Methoxyphenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Normal University; Fan Xuesen; Song Xia; Zhang Xinying; (24 pag.)CN110746319; (2020); 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. 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(2-Hydroxyethyl)benzonitrile

Preparation 5 Preparation of 4-carbamoylphenethyl bromide STR39 A solution of phosphorus tribromide (5 g) in carbon tetrachloride (10 ml) was added, dropwise, to a solution of 4-cyanophenethyl alcohol (8.06 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours. On cooling to room temperature, the mixture was poured onto ice (200 g). The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to give a colourless oil which solidified on standing. The solid was chromatographed on silica eluding with ethyl acetate containing hexane (20%). The fractions containing the less polar (higher Rf) product were combined and concentrated in vacuo to give 4-cyanophenethyl bromide as a yellow oil which solidified on standing, yield 8.9 g. The fractions containing the more polar (lower Rf) product were combined and concentrated in vacuo to give the title compound as a colourless solid, yield 0.47 g, m.p. 152-153. 1 H N.m.r. (CDCl3)delta=7.85 (d, 2H); 7.35 (d, 2H); 6.20-5.70 (brd, 2H); 3.70-3.60 (m, 2H); 3.35-3.20 (m, 2H) ppm.

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 69395-13-7.

Reference:
Patent; Pfizer Inc; US5422358; (1995); A;,
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Application of 50846-36-1, 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. 50846-36-1, name is 2-Amino-2-methylpropanenitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 5-(6-ethoxy-2-(4-fluorophenyl)-3- (methylcarbamoyl)benzofuran-5-yl)-2-(methoxy-i)nicotinic acid (35 mg, 0.075 mmol) and 2-amino-2-methylpropanenitrile hydrochloride (9.03 mg, 0.075 mmol) in DMF (5.0 mL) at room temperature under a nitrogen atmosphere was added DIPEA (0.065 mL, 0.374 mmol). The mixture was cooled to 0C, and HATU (42.7 mg, 0.112 mmol) was added to the mixture. The reaction mixture was stirred at room temperature for 16 hr. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water, stirred for 5 min and the solid filtered. The crude product was purified by Prep HPLC to obtained the desired compound as a white solid. Yield: 11.50 mg, (28.79 %). PREPARATIVE HPLC: Column: Sunfire C-18(19* 150)mm*5um, Mobile Phase: 20mM Ammonium acetate pH 4.5 with acetic acid (A): MeCN (B), Flow: 18 ml/min, Rt: 10.74 min. NMR (400MHz, DMSO- de) delta ppm = 8.62 (s, 1 H), 8.50 (d, J= 2.4 Hz, 1 H), 8.44 (d, J= 4.6 Hz, 1 H), 8.23 (s, 1 H), 8.00 – 7.96 (m, 2 H), 7.58 (s, 1 H), 7.50 (s, 1 H), 7.41 – 7.36 (m, 2 H), 4.17 (q, J = 7.0 Hz, 2 H), 2.84 (d, J= 4.6 Hz, 3 H), 1.72 (s, 6 H), 1.32 (t, J= 6.9 Hz, 3 H). 19F NMR (376.6 MHz, DMSO-de) delta: -111.37. LCMS: (ES+) m/z = 534.4 (M+H)+, Column- Acentis Express C18 (50 x 2.1 mm; 2.7 um), Buffer : lOmM Ammonium Acetate pH-5 adjusted with HCOOH, Mobile phase A: Buffer : MeCN (95:5), Mobile phase B: Buffer : MeCN (5:95), Flow: 0.8 ml/min. Rt: 1.11 min, wavelength: 220nm. HPLC Method: SUNFIRE (150 X4.6mm) 3.5micron, Buffer: 0.05% TFA in water pH 2.5, Mobile Phase A: Buffer: MeCN (95:5), Mobile Phase B: MeCN: Buffer (95:5), Flow: 1.0 ml/min, Wavelength: 254 nm, Rt: 19.96 min, Wavelength: 220 nm, Rt: 19.96 min. HPLC Method: XBridge Phenyl (150 X4.6mm) 3.5micron SC/749, Buffer: 0.05% TFA in water pH 2.5, Mobile Phase A: Buffer: MeCN (95:5), Mobile Phase B: Buffer: MeCN (5:95), Flow: 1.0 ml/min, Wavelength: 254 nm, Rt: 16.94 min, Wavelength: 220 nm, Rt: 16.94 min.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; KADOW, John F.; BORA, Rajesh Onkardas; ANJANAPPA, Prakash; GUPTA, Samayamunthula Venkata Satya Arun Kumar; (148 pag.)WO2016/137832; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 51762-67-5, name is 3-Nitrophthalonitrile, 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 51762-67-5, Safety of 3-Nitrophthalonitrile

3-Hydroxypthalonitrile was synthesized according to the literature method [22]. To a 50 mL round-bottom flask were added 3-nitropthalonitrile (2.0 g, 11.6 mmol), K2CO3 (1.8 g, 12.7 mmol) and NaNO2 (0.8g, 11.6 mmol) in DMSO (30 mL), and the reaction mixture was stirred under reflux for 30 min. After cooling to room temperature, the reaction mixture was diluted with water (90 mL) and subsequently acidified with 2M HCl to pH=3 to produce a precipitate. Then, the solid was collected by filtration and washed successively with water and methanol. The pure product was obtained by recrystallization in acetic acid as a brown crystal (0.8 g, 48%). Mp: 263-265C.

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:
Article; Chen, Wenqiang; Chen, Song; Zhou, Bingjiang; Wang, Hongbo; Song, Xiangzhi; Zhang, Hongyan; Dyes and Pigments; vol. 113; (2015); p. 596 – 601;,
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Application of 3759-28-2, These common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, 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.

100ml of water was added to the reaction vessel, 20mmol (o-cyanophenyl)acetonitrile, 40mmol of potassium (m-tolyl)trifluoroborate 0.4mmol palladium acetylacetonate, 0.8mmol nitrogen ligands L-1, and p-toluenesulfonic acid monohydrate 100mmol, in The reaction was stirred at 60 deg.] C for 30 hours.AntiAfter should be ended, the mixture was poured into ethyl acetate, sequentially with saturated NaHCO3solutionand brine, the aqueous layer was extracted with ethyl acetate, the organic layers combined (i.e., combined washedorganic layer and the extract obtained the organic layer), dried over anhydrous of Na2the SO4dried, vacuum is removed by evaporationof the solvent, the residue was purified by flash column chromatography (hexane / ethyl acetate, volume ratio of between1: 1) to give the target liquid product.The yield was 72.5%,% purity was 99.1(the HPLC).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou University; CHEN, JIUXI; LIU, MIAOCHANG; CHENG, TIANXING; WANG, XIAODONG; GAO, WENXIA; HUANG, XIAOBO; WU, HUAYUE; (14 pag.)CN104557701; (2016); B;,
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1885-29-6, name is 2-Aminobenzonitrile, 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. name: 2-Aminobenzonitrile

b) 2- {[(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile To a solution of 2-aminobenzonitrile (3 g) in acetonitrile (30 ML) was added 5- (methoxymethylene) -2, 2-DIMETHYL-1, 3-dioxane-4,6-dione (4.73 g) in acetonitrile (10 mL). After 2 minutes of stirring, a fine suspension developed which was filtered to afford the titled product (4.3 g). H NMR (400 MHZ, D6-DMSO) 6 11.60 (1H, d), 8. 72 (1H, d), 7.93 (2H, t), 7.79 (1H, TD), 7.44 (1H, td), 1.70 (6H, s).

The synthetic route of 1885-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/113303; (2004); A1;,
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Application of 115279-57-7, 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (6.4 g, 23.6 mmol) and 2-(4-aminophenyl)-2-methylpropionitrile (5.6 g, 35 mmol) were dissolved in tert-butanol (200 mL), to the system added potassium carbonate (16.4 g, 119 mmol), and the reaction mixture was stirred under reflux for 2 h. After confirming a disappearance of the raw materials by a thin layer chromatography plate (ethyl acetate:petroleum ether=1:3), the reaction mixture was suction filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether to give 8.1 g of a pale yellow solid.

The synthetic route of 2-(4-Aminophenyl)-2-methylpropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Wu, Frank; Zhang, Yan; US2015/166539; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3215-64-3, name is 2-(2,6-Dichlorophenyl)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 3215-64-3, Safety of 2-(2,6-Dichlorophenyl)acetonitrile

4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (l-2a) (3.1 g, 18 mmol) was dissolved in 40 rtiL anhydrous dimethylformamide and cooled in an ice/methanol bath (-10 C) for 15 minutes under an atmosphere of nitrogen. Sodium hydride (0.73 g, 18 mmol) divided into 5 portions was added over the course of 5 minutes keeping the reaction mixture cooled with stirring. After an additional 5 minutes, a solution of 2,6-dichlorobenzylacetonitrile (1-la) (4.9 g, 27 mmol) in 12 mL anhydrous dimethylformamide was added drop wise via syringe. The resulting mixture was stirred at -10 C for 30 minutes then allowed to warm to room temperature overnight after which time the reaction mixture was cooled in an ice bath and slowly quenched with 50 mL saturated NEUCl. After stirring for 20 minutes the product was extracted into DCM. The combined DCM extracts were dried over MgSCk, filtered, and concentrated under reduced pressure. The residue was re-dissolved in ethyl acetate and washed with brine. The organic layer was filtered through a sintered glass funnel and the filtrate was dried over sodium sulfate, filtered, and concentrated under reduced pressure to dryness. The residue was purified by silica gel chromatography eluting with ethyl acetate/dichloromethane to afford 708 mg (11%) 6-(2,6- dichlorophenyl)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-amine (l-3a). LCMS (ESI):[M+H]? = 336.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2,6-Dichlorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ACHAOGEN, INC.; COHEN, Frederick; KANE, Timothy Robert; DOZZO, Paola; HILDEBRANDT, Darin James; LINSELL, Martin Sheringham; MACHAJEWSKI, Timothy D.; MCENROE, Glenn A.; (172 pag.)WO2018/23081; (2018); 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. 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C6H4N4

General procedure: In a 25 mL round bottom flask, a mixture of 2,3-dihydroxynaphthalene (1 mmol),aldehyde (1 mmol), malononitrile (1 mmol) or 2-aminoprop-1-ene-1,1,3-tricarbonitrile (1 mmol) and guanidine hydrochloride (10 mol%) were taken, and the mixture was stirred at 100C in an oil bath for an appropriate amount of time as indicated in Tables 3 and 4. The progress of the reaction was monitored by thin-layerchromatography (TLC). After completion, the reaction mixture was cooled to room temperature and CH3CN (5 mL) was added, and then a precipitate was allowed to form. The precipitate was filtered, washed with CH3CN and dried. The crude product was stirred for 5 min in boiling EtOH,and the resulting precipitate was filtered. The product 4 and 9 thus obtained was found to be pure upon 1H and 13CNMR, mass spectra, elemental analyses, and TLC examination.

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:
Article; Olyaei, Abolfazl; Shahsavari, Mohammad Sadegh; Sadeghpour, Mahdieh; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 943 – 956;,
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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, name: 3,3-Diethoxypropanenitrile

Step 1. l-cyclopropyl-lH-pyrazol-5-amine [0634] A 100-mL round-bottom flask was charged with 3,3-diethoxypropanenitrile (0.600 g, 4.19 mmol), cyclopropylhydrazine di-hydrochloride (0.610 g, 4.21 mmol) and ethanol (20 mL), and the resulting solution stirred for 18 h at 80 C. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10: 1, dichloromethane/methanol) to afford l-cyclopropyl-lH-pyrazol-5-amine (0.206 g, 36% ) as light yellow oil. MS (ESI, pos. ion) m/z 124[M+H]+.

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; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
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