Tag: M.W=100-200

Application of 591769-05-0,Some common heterocyclic compound, 591769-05-0, name is 3-Cyclopentylacrylonitrile, molecular formula is C8H11N, 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 solution of 4-(lH-pyrazol-4-yl)pynOlo[l,2-b]pyridazine-3-carbonitrile 16a (60 mg, 0.287 mmol) in DMF (1.5 mL) was added 3-cyclopentylacrylonitrile (109 mg, 0.717 mmol), 2,3,4,6,7,8,9, 10-octahydropyrimido[l,2-a]azepine (0.270 mL, 1.772 mmol) and heated with stirring at 50 °C for 3 h. The reaction mixture was cooled to RT and concentrated in vacuum to dryness. The residue obtained was purified by combiflash column chromatography [silica gel, 4 g eluting with hexanes/ethyl acetate (1 :0 to 2:1)] to give 4-(l-(2-cyano-l-cyclopentylethyl)-lH- pyrazol-4-yl)pyrrolo[l,2-b]pyridazine-3-carbonitrile 16b (56 mg, 59percent, Rf = 0.42 with hexanes/ethyl acetate = 2:1) as a yellow solid; 1H NMR (300 MHz, OMSO-d6) delta 8.80 (d, J= 0.6 Hz, 1H), 8.48 (s, 1H), 8.31 (s, 1H), 8.19 (t, J= 2.1 Hz, 1H), 7.13 (d, J= 2.0 Hz, 2H), 4.64 (td, J = 9.0, 4.8 Hz, 1H), 3.29 – 3.21 (m, 2H), 2.48 – 2.37 (m, 1H), 1.91 – 1.11 (m, 8H).

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

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; WU, Minwan; WO2011/150356; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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 53312-81-5, Safety of 5-Amino-2-fluorobenzonitrile

General procedure: To the solution of carboxylic acid (1 eq.) in DCM were added HATU (1.05 eq.), amine (1.1 eq.) and DIPEA (2 eq.). The mixture was stirred for 16 h at room temperature. Afterwards, the solution was washed with water and brine. The resulting organic layer was dried over MgSO4, and the solvent was removed by evaporation. The crude material was purified by flash chromatography (CH2Cl2:MeOH).

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Egyed, Attila; Bajusz, David; Keser?, Gyoergy M.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1497 – 1508;,
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Adding a certain compound to certain chemical reactions, such as: 6621-59-6, name is 6-Bromohexanenitrile, 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 6621-59-6, Safety of 6-Bromohexanenitrile

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

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

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
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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 654-70-6 as follows. HPLC of Formula: C8H5F3N2

2-Isopropoxy-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-4-Cyano-3-trifluoromethyl-phenyl)-2-Isopropoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.01 (7H,aromatic), delta4.04(1H,m,OCH), delta1.38(6H,d,Methyl)

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kundu, Tapas Kumar; Balasubramanyam, Karanam; Swaminathan, Vankatesh; US2006/167107; (2006); A1;,
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Reference of 2973-50-4, These common heterocyclic compound, 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, 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.

General procedure: In an Erlenmeyer flask, 2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazide (4) (1.0 mmol), aromatic nitriles (1.0 mmol) and DMAP (30 mol%) were taken in ethanol (15 mL). The reaction mixture was irradiated inside a synthetic microwave oven (Make-Ethosi Milestone with temperature control) for about 20-25 min (700 W). After completion of reaction (monitored by TLC), the mixture was concentrated to obtain the solid product. The solid product formed was filtered, dried and recrystallized from ethanol.

Statistics shows that 2-(2-Aminophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 2973-50-4.

Reference:
Article; Sangshetti, Jaiprakash N.; Kalam Khan, Firoz A.; Chouthe, Rashmi S.; Damale, Manoj G.; Shinde, Devanand B.; Chinese Chemical Letters; vol. 25; 7; (2014); p. 1033 – 1038;,
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Electric Literature of 77326-36-4,Some common heterocyclic compound, 77326-36-4, name is 2-Amino-6-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.

Sodium hydride (0.154 g, 3.85 mmol, 1.5 equiv) was added to a mixture of 2-amino-6-fluorobenzonitrile (0.524 g, 3.85 mmol, 1.5 equiv) and 2-methyl-2-((5-methylpyrimidin-2-yl)amino)propan-1-ol (Example 1b, 0.465 g,2.56 mmol, 1 equiv) in anhydrous THF (25 mL) under nitrogen. The reaction mixture was stirred for 10 minutes at room temperature and refluxed for 21 h. The reaction mixture was concentrated and the residue was purified by chromatography on a silica(50% EtOAc in Hexanes gradient) to provide the title compound (611 mg, 80% yield), MS 298 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-fluorobenzonitrile, its application will become more common.

Reference:
Patent; FIRMENICH INCORPORATED; FOTSING, Joseph, R.; TACHDJIAN, Catherine; SERVANT, Guy; CHING, Brett, Weylan; DAVIS, Timothy; (94 pag.)WO2020/33420; (2020); A1;,
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Application of 14447-18-8, A common heterocyclic compound, 14447-18-8, name is Benzyl cyanoacetate, molecular formula is C10H9NO2, 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.

4b (0.30 g, 1.15 mmol) and 6a (0.24 g, 1.38 mmol) were dissolved in tetrahydrofuran (10 mL). Piperidine (11 muL, 0.11 mmol) was then dissolved and stirred at 50 C. for 10 hours. After the reaction was completed, the mixture was cooled at room temperature and extracted with ethyl acetate. The organic solvent layer was collected, and water was removed with magnesium sulfate, followed by concentration under reduced pressure. The resulting concentrate was purified by silica gel column chromatography (hexane: acetone: ethyl acetate = 3: 1: 1) to give compound 8a in 65% yield in the form of a purple powder.

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; Konkuk University Industry-Academic Cooperation Foundation; Jung, Yoo Hoon; Park, Kwang Soo; So, Yoo Jin; (14 pag.)KR101728909; (2017); B1;,
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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. 19179-31-8, name is 3,5-Dimethoxybenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO2

To a solution of 3,5-dimethoxybenzonitrile (2 g, 12.2 mmol) in dichloromethane (20 was added slowly BBr3 (15 mL, 1 M, 15 mmol) at -50 C under N2. After addition, the mixture was stirred at -50 C for 2 h and stirred at r.t for 20 hr. The mixture was slowly poured into ice-water with stirring and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column (petroleum ether/ethyl acetate (2: 1) as eluent) to afford 3,5- dihydroxybenzonitrile (1.43 g). 1H NMR (DMSO-d6, 400 MHz): delta 10.02 (s, 2H), 6.56 (d, J= 2.0 Hz, 2H), 6.51 (t, J = 2.0 Hz? 1H).

The synthetic route of 19179-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARRINGTON, Kenneth, L.; BURGEY, Christopher; GILFILLAN, Robert; HAN, Yongxin; PATEL, Mehul; LI, Chun Sing; LI, Yaozong; LUO, Yunfu; LEI, Zhiyu; XU, Jiayi; WO2014/58747; (2014); A1;,
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Electric Literature of 873-74-5, 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. 873-74-5 name is 4-Aminobenzonitrile, 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.

The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is p-cyanoaniline, the reaction time is 12 h, and the other reaction and post-treatment processes are the same as in the embodiment 28. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 mol%, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 C for 2 h, and the other reactions and workup procedures were the same as in Example 1.

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

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Gao Xianying; Geng Yang; Han Shuaijun; Liang Apeng; Li Jingya; Zou Dapeng; Wu Yangjie; (19 pag.)CN108503552; (2018); A;,
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Synthetic Route of 64248-62-0, 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. 64248-62-0 name is 3,4-Difluorobenzonitrile, 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.

3,4-difluorobenzonitrile (2.500 g, 17.973 mmol), titanium isoproxoxide (6.917 mL, 23.364 mmol) and ethylmagnesium bromide (1.00 M solution in THF, 41.337 mL, 41.337 mmol) was dissolved in 2-methoxy-2-methylpropane (MTBE, 30 mL), at -20 C and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture borontrifluoride diethyl etherate (4.436 mL, 35.945 mmol) was added and further stirring at room temperature for 3 hours, then, at room temperature, sodium hydroxide (3.00 M solution in water, 17.973 mL, 53.918 mmol) was added and the reaction was terminated by stirring for 30 minutes. The reaction mixture was filtered through a pad of celite to remove the solid. Water was poured into the filtrate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; methanol / dichloromethane = 5% to 30%) and concentrated to give the title compound (0.822 g, 27.0%) as a light yellow liquid.

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

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
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