Tag: M.W=100-200

Synthetic Route of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 a 3 -neck flask with an internal thermometer and an addition funnel was added (i?)-(+)-2-methyl-CBS-oxazaborolidine solution in toluene (3.0 mL) and borane-dimethylsulfide (300 The reaction was stirred at room temperature for 10 min then diluted with DCM (25 mL). Borane-dimethylsulfide (6.0 mL) was added and, after stirring for 5 min, the reaction was cooled to -20C. l-Oxo-2,3-dihydro-7H- indene-4-carbonitrile INT-1 (4.7 g, 30 mmol) in DCM (25 mL) was added dropwise by addition funnel over 20 min while maintaining the reaction at -20 ¡À 5C. The reaction was stirred for 1 h then quenched by the dropwise addition of MeOH (20 mL). After hydrogen evolution ceased, MeOH (30 mL) was added and removed by heating at atmospheric pressure. MeOH (50 mL) was added in two and removed by heating twice. All the solvent was evaporated to give a solid which was recrystallized from EA (9 mL) and hexane (22 mL). The compound was filtered and washed with 5: 1 hexane/EA (30 mL) to provide 3.73 g (78%) of (5)-l-hydroxy-2,3-dihydro-iH-indene-4-carbonitrile INT-2 as a white powder. LCMS-ESI (m/z) calculated for Ci0H9NO: 159.1; found 160.1 [M+H]+, tR = 2.39 min. 1H NMR (400 MHz, CDC13) delta 7.62 (d, J = 7.6 Hz, 1H), 7.53 (d, J = 7.6 Hz, 1H), 7.32 (t, J = 7.6 Hz, 1H), 5.28 (d, J = 4.1 Hz, 1H), 3.23 (ddd, J = 17.0, 8.7, 4.4 Hz, 1H), 3.04 – 2.90 (m, 1H), 2.64 – 2.51 (m, 1H), 2.00 (dddd, J= 13.4, 8.7, 7.1, 5.7 Hz, 1H), 1.91 (d, J = 5.4 Hz, 1H). Chiral HPLC: (5)-l-hydroxy-2,3- dihydro-iH-indene-4-carbonitrile was eluted in 20% IPA in hexane: >99.9% ee, = 7.42 min. The (i?)-enantiomer was obtained in an analogous fashion using (S) -(-)-2- methyl-CBS-oxazaborolidine. for (i?)-enantiomer = 6.79 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; RECEPTOS, INC.; MARTINBOROUGH, Esther; BOEHM, Marcus, F.; YEAGER, Adam, Richard; TAMIYA, Junko; HUANG, Liming; BRAHMACHARY, Enugurthi; MOORJANI, Manisha; TIMONY, Gregg, Alan; BROOKS, Jennifer, L.; PEACH, Robert; SCOTT, Fiona, Lorraine; HANSON, Michael, Allen; WO2015/66515; (2015); A1;,
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Related Products of 658-99-1, 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. 658-99-1 name is 2-(3,4-Difluorophenyl)acetonitrile, 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.

EXAMPLE 17; N-{[2-[(3,4-Difluorophenyl)methyl]-4-hydroxy-6-oxo-1-(phenylmethyl)-1,6-dihydro-5-pyrimidinyl]carbonyl}glycine; 17a) Ethyl 2-(3,4-difluorophenyl)ethanimidoate hydrochloride; 3,4-Difluoroacetonitrile (2.44 g, 15.93 mmol) and ethanol (2 mL) was sealed in a flask using a rubber septum and flushed with nitrogen. 4 Molar hydrogen chloride in dioxane (5 mL) was added and the mixture was stirred at rt overnight. The solid was diluted with diethyl ether, collected, washed with diethyl ether and dried in vacuo to give the title compound (2.87 g, 76.5%) 1H NMR (400 MHz, DMSO-d6) delta ppm 11.75 (br. s., 2 H), 7.37-7.67 (m, 2 H), 7.20-7.31 (m, 1 H), 4.41 (q, J=7.07 Hz, 2 H), 4.05 (s, 2 H), 1.29 (t, J=6.95 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3,4-Difluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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Related Products of 1080-74-6, 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 1080-74-6 as follows.

To a three-necked round bottom flask were added 5,5′-(9,9′-spirobi[fluorene]-2,7-diyl)bis(4-(2-ethylhexyl)thiophene-2-carbaldehyde) (220 mg, 0.29 mmol), 1,1-dicyanomethylene-3-indanone (432 mg, 2.2 mmol), chloroform (50 mL), and 0.9 mLpyridine. The mixture was deoxygenated with nitrogen for 30 minand then refluxed for 12 h. After cooling down to room temperature,the mixture was poured into methanol (200 mL) and filtered.The residue was purified by column chromatography on silica gelusing petroleum ether/dichloromethane (1:1) as eluent yield anorange solid (213 mg, 66%). 1H NMR (400 MHz, CDCl3): delta 8.78 (s,2H), 8.68 (d, J 6.9 Hz, 2H), 7.99 (d, J 8.1 Hz, 2H), 7.90 (m, 4H), 7.78 (m, 4H), 7.62 (d, J 8.4 Hz, 4H), 7.41 (t, J 7.5 Hz, 2H), 7.17 (t,J 7.5 Hz, 2H), 6.90 (s, 2H), 6.82 (d, J 7.5 Hz, 2H), 2.38 (d,J 7.2 Hz, 4H), 1.39 (m, 2H), 1.11 (m, 4H), 1.06 (m, 12H), 0.81 (t,J 7.2 Hz, 6H), 0.61 (t, J 7.2 Hz, 6H). 13C NMR (100 MHz, CDCl3): delta 188.78,161.17,157.01, 150.60,148.23, 148.06,142.35,141.37,140.50,138.73, 137.48, 135.75, 135.55, 135.15, 134.12, 130.13, 128.78, 128.70,125.92, 125.42, 124.50, 124.41, 123.29, 121.33, 120,89, 115.07, 114.98,70.38, 66.55, 40.61, 32.88, 32.58, 28.86, 25.82, 23.49, 14.72, 10.89.10.92. MS (MALDI): m/z calcd for C75H60N4O2S2: 1113.4; found:1113.0. Anal. Calcd for C75H60N4O2S2: C, 80.90; H, 5.43; N, 5.03.Found: C, 80.90; H, 5.47; N, 5.12.

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Jiayu; Dai, Shuixing; Yao, Yuehan; Cheng, Pei; Lin, Yuze; Zhan, Xiaowei; Dyes and Pigments; vol. 123; (2015); p. 16 – 25;,
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Synthetic Route of 53312-81-5,Some common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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: Under nitrogen atmosphere, dry CH2Cl2 (30 mL), amine (0.02 mol), and Et3N (0.05 mol) wereadded to a three-necked round bottom ask and stirred for 0.5 h, then chloroacetyl chloride droppedslowly and reacted for 3 h at room temperature. Then, the solution was washed with 2 mol L1hydrochloric acid (30 mL), saturated aq NaHCO3 solution (30 mL), and brine (40 mL), successively,then dried over anhydrous Na2SO4 and filtered. After evaporating CH2Cl2 in vacuum, the obtainedcrude product was rened by recrystallization using ethyl acetate/petroleum ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Article; Cai, Nan; Liu, Caixiu; Feng, Zhihui; Li, Xinghai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Ahmed, Wasim; Cui, Zining; Molecules; vol. 23; 4; (2018);,
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Reference of 90381-43-4, 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. 90381-43-4, name is 7-Methoxy-2-naphthonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparative Example 6 7-Cyano-2-methoxy-1-naphthaldehyde STR28 Under nitrogen atmosphere, 3.7 g of 2-cyano-7-methoxynaphthalene was dissolved in 40 ml of dichloro-methane, and 6.6 ml of titanium tetrachloride and 4.6 ml of dichloromethyl methyl ether were added dropwise into the resulting solution at 0 C. in this order. The resulting mixture was stirred at room temperature for 30 minutes and cooled to 0 C. again. Water was added to the resulting mixture to cease the reaction, and the resulting mixture was extracted with dichloromethane (100 ml*2). The organic layers were combined, washed with water, da saturated aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and the resulting crude crystal was washed with ether and dried to give 3.3 g of the title compound as colorless crystals. 1 H–NMR (CDCl3, 400 MHz) delta; 4.10(s,3H), 7.48(d,1H, J=8.8 Hz), 7.57(dd,1H, J=1.2,8.4 Hz), 7.86(d,1H,J=8.4 Hz), 8.11(d,1H,J=8.8 Hz), 9.74(s,1H), 10.87(s,1H).

The synthetic route of 7-Methoxy-2-naphthonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US6110959; (2000); A;,
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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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-3-methylbenzonitrile

(E)-methyl 3-(4-cyano-2-methylphenyl)acrylateTo a solution of 4-bromo-3-methylbenzonitrile (0.784 g, 4 mmol) in DMF (20 ml_) was added methyl acrylate (1.812 ml_, 20.00 mmol), DIPEA (1.747 ml_, 10.00 mmol), Pd(OAc)2(0.090 g, 0.400 mmol) and tri-o-tolylphosphine (0.243 g, 0.800 mmol). The reaction mixture was then heated with microwave irradiation at 150 C under N2atmosphere for 1 h. The reaction mixture was evaporated under vacuum to remove remaining methyl acrylate, then diluted with H20 (20 ml_), extracted with EtOAc (3 x 40 ml_). The combined organic layer was washed with brine (50 ml_), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product (E)-methyl 3-(4-cyano-2-methylphenyl)acrylate (0.8815 g, 4.38 mmol, 110 % yield). H-NMR (400 MHz, CHLOROFORM-d) delta ppm 2.47 (s, 3 H) 3.84 (s, 3 H) 6.43 (d, J=15.81 Hz, 1 H) 7.47 – 7.55 (m, 2 H) 7.61 (d, J=8.53 Hz, 1 H) 7.92 (d, J=15.81 Hz, 1 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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (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. 3441-01-8, name is 3-Cyanobenzamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6N2O

Example 100 3-cyano-A-[10,ll-dichloro-4-oxo-3-(trifluoromethyl)-2,5,7-triazatricyclo[6.4.0.02’6]dodeca- l(8),6,9,ll-tetraen-3-yl]benzamide (ABR 239453) To a stirred solution of 3-cyanobenzamide (650 mg, 4.45 mmol) in DMF (7 mL) was added pyridine (378 mu, 4.45 mmol) followed by ethyl 3,3,3-trifluoro-2-oxopropanoate (590 mu, 4.45 mmol) at room temperature under argon. The reaction mixture was stirred at room temperature for 1 h. Thionyl chloride (323 mu, 4.45 mmol) was added at 0¡ãC. The reaction mixture was then stirred at room temperature for a further 16 h and before the reaction mixture was concentrated. The acyl intermediate that remained was dissolved in DMF (5 mL) under argon. 5,6-Dichloro- lH-l,3-benzodiazol-2-amine (674 mg, 3.34 mmol) and triethylamine (934 mu, 6.67 mmol) were added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SC>4), filtered and concentrated. The crude product was purified by silica chromatography, using 3percent MeOH in DCM as eluent. Further purification was carried out by trituration in DCM/MeOH and then pentane to afford the title compound as a white solid (25 mg, 1percent).

According to the analysis of related databases, 3441-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTIVE BIOTECH AB; WELLMAR, Ulf; LIBERG, David; EKBLAD, Maria; BAINBRIDGE, Marie; EAST, Stephen; HARGRAVE, Jonathan; PREVOST, Natacha; WO2015/177367; (2015); A1;,
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These common heterocyclic compound, 628-20-6, name is 4-Chlorobutyronitrile, 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. name: 4-Chlorobutyronitrile

1L three-necked flask 600ml of anhydrous ethanol under ice four hours continuously fed ammonia to saturation;pressurized cylinders ethanol was added a saturated solution of ammonia had been prepared, and then added 103.5g 4-chlorobutyronitrile (lmol), sealed in an oil bath heated 100-120 C, 10 hours;After completion of the reaction, cooled to room temperature, the reaction solution was spin to 70% ethanol, the precipitated solid was filtered, and the mother liquor was recrystallized with ether to give a solid, solids were combined to give a pale yellow solid drying 89.2g,No. HHC-014-A, Yield 74%

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

Reference:
Patent; Nanjing Pharmatechs Co., Ltd; Zhang, Xiaowen; Yang, Jie; (5 pag.)CN103435617; (2016); B;,
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Some common heterocyclic compound, 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, molecular formula is C8H6FN, 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. Computed Properties of C8H6FN

[0144] 4-Fluoro-2-methylbenzonitrile (2.9g), 5N NaOH (50 mL), and MeOH (50 mL) were set stirring at 100 ¡ãC for 18 hours. The solvent was removed under reduced pressure and the product was washed with CH2CI2 and acidified to pH 1. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried overanhydrous Na2S04 to yield a while solid (1.6 g). *H NMR (300 MHz, CDC13): 5 8.07-8.14 (m, 1H), 6.96-7.01 (m, 1H), 6.79-6.82 (m, 1H), 2.73 (br s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147754-12-9, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
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Synthetic Route of 25309-65-3, 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. 25309-65-3, name is 4-Ethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 27 Preparation of 2-(p-ethylphenyl)-5(6)-methoxybenzimidazole 5.0 g. of p-ethylbenzonitrile in 40 ml. of methanolic hydrochloric acid was stirred at room temperature overnight. The reaction mixture was diluted with water, neutralized with sodium carbonate and extracted with n-hexane. The extract was evaporated in vacuo to remove n-hexane. The remaining alkoxyimine compound was dissolved in methanol and 4.7 g. of p-anisidine was added thereto. The mixture was warmed for 30 minutes and evaporated in vacuo to remove methanol, whereby N-(p-methoxyphenyl)-4-ethylbenzamidine was recovered. This product was dissolved in water and then acidified with hydrochloric acid.

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

Reference:
Patent; Kanebo, Ltd.; US4188486; (1980); A;,
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