Tag: M.W=0-100

3047-38-9, name is Cyclopent-1-enecarbonitrile, 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: Cyclopent-1-enecarbonitrile

Into a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-3-amine (1-1; 250 g, 1.04 mol), ethanol (3000 mL), cyclopent-l-ene-l-carbonitrile (300 g, 3.22 mol), and DBU (317 g, 2.08 mol). The resulting solution was heated to reflux and stirred overnight. The reaction mixture was cooled and concentrated in vacuo, and the resulting residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10-1 :2) to afford racemic-2-[3- amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 -yljcyclopentane- 1 -carbonitrile. The racemic 2-[3-amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 – yljcyclopentane- 1 -carbonitrile (100 g, 300 mmol) was purified using Chiral Prep-SFC with the following conditions: Column Used: Phenomenex Lux Cellulose-4, 2 x 25cm, 5 muiotaeta Mobile phase: C02 (80%), methanol with 0.1% DEA (20%) Wavelength: UV 254 nm. Peak A, 1-6: (lR,2R)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane- 1 -carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H). Peak B, 1-7: (llS’,2lS,)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane-l- carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H).

The synthetic route of 3047-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
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Reference of 6011-14-9,Some common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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: 2-Aminoacetonitrile hydrochloride 2 (7.0 mmol) and sodium acetate (8.0 mmol) were dissolved in 35 mL of methanol. Aldehyde 1 (7.0 mmol) was added to the grey solution, and the reaction mixture was stirred at room temperature. A solid suspension was formed after a few minutes (for compounds 3a, 3c, 3f and 3g). The suspension was stirred for 2 h and the solid filtered and washed with cold methanol, leading to the pure product 3. A second crop was isolated from the mother liquor after complete removal of methanol in the rotary evaporator, addition of dichloromethane (40 mL) and dry flash chromatography of the solution using dichloromethane (4×10 mL) as eluent. The solution was concentrated in the rotary evaporator and the yellow oil was kept at 0 C leading to the product 3 that was filtered and washed with cold diethyl ether. For compounds 3b, 3d, 3e and 3h-k, the reaction mixture was stirred at room temperature for 2 h. The solvent was removed in the rotary evaporator and dichloromethane (40 mL) was added to the mixture. Dry flash chromatography of this mixture was performed using 20 mL of dichloromethane as eluent. The solvent was removed in the rotary evaporator leading to a solid product. Cold diethyl ether was added to the suspension, kept for a few minutes in an ice bath. The solid was filtered and washed with cold diethyl ether, leading to the pure (arylideneamino)acetonitrile 3.

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

Reference:
Article; Costa, Marta; Proena, Fernanda; Tetrahedron; vol. 67; 10; (2011); p. 1799 – 1804;,
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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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 630-18-2

1-(Benzo[h]quinolin-2-yl)-2,2-dimethylpropanone. A solution of 2-bromobenzo[h]quinoline (1.52 g, 5.89 mmol) in THF (36 ml) was cooled to -78 C. and after 10 minutes a solution of 2.5 M of n-butyllithium in n-hexane (2.47 ml, 6.18 mmol) was added slowly. The resulting dark red solution was stirred at this temperature for 1 hour and then a solution of 2,2-dimethylpropanonitrile (0.78 ml, 7.04 mmol) in THF (5 ml) was added drop-wise. The solution was stirred for a further hour at -78 C. and finally allowed to warm slowly to ambient temperature. A solution of 1M H2SO4 (25 ml, 25 mmol) was then added and the mixture was heated under reflux for 3 hours. After cooling, the organic phase was separated and the aqueous phase was extracted with Et2O (3*15 ml). The organic phases were combined, dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (eluent: petroleum ether/acetate=9/1) to give 1.24 g (80% yield) of 1-(benzo[h]quinolin-2-yl)-2,2-dimethylpropanone in the form of a yellow solid; melting point: 88-90 C. Elemental analysis (%) calculated for C18H17NO: C, 82.10; H, 6.51; N, 5.32. Found: C, 82.10; H, 6.51; N, 5.32. 1H NMR (CDCl3): delta 9.20 (d, J=7.8 Hz, 1H), 8.13 (s, 2H), 7.84 (d, J=7.8 Hz, 1H), 7.80-7.73 (m, 2H), 7.73-7.62 (m, 1H), 7.56 (d, J=9 Hz, 1H), 1.67 (s, 9H). 13C{1H} NMR (CDCl3): delta 206.7, 152.1, 144.5, 136.3, 133.7, 131.8, 129.5, 128.4, 127.9, 127.5, 124.9, 124.5, 121.2, 44.3, 28.0.

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; Rigo, Pierluigi; Baratta, Walter; Siega, Katia; Chelucci, Giorgio Adolfo; Ballico, Maurizio; Magnolia, Santo; US2010/152448; (2010); 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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C5H9N

Preparation of the imino ester: A mixture of 8.3 g (0.1 mole) of trimethyl acetonitrile and 5.05 g of EtOH (0.11 mole) is treated with HCI gas at 5 0C until saturation. The mixture is then stored at the same temperature for 18 h and 20 ml of DEE are added. The resulting precipitate is collected by filtration, ished with DEE and dried to yield 3.9 g (24%) of the crude imino ester hydrochloride as a white solid. (1H- NMR (400 MHz, DMSO-O6): delta = 4.42 (q, 2H), 1.35 (t, 3H), 1.25 (s, 9H)).

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; NOVARTIS AG; WO2008/71404; (2008); A1;,
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Electric Literature of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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 stirring solution of crude 8-fluoro-4-hy- drazinylquinoline (0.27 g, 1.5 mmol) and 3-oxo-butyroni- trile (0.15 g, 0.19 mmol) in pyridine (3 mE) was heated at 80 C. for 15 h. After cooling to room temperature, aqueous saturated sodium bicarbonate was added to the reaction mixture and extracted with dichioromethane (3x 10 mE). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was used directly without thrther purification (0.14 g, 0.76 mmol, 50%)

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

Reference:
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (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. 4426-11-3, name is Cyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Cyclobutanecarbonitrile

Example 234A 1-(6-(trifluoromethyl)pyridin-2-yl)cyclobutanecarbonitrile Cyclobutanecarbonitrile (1.474 g, 18.17 mmol) and 2-fluoro-6-(trifluoromethyl)pyridine (2.0 g, 12.11 mmol) were dissolved in toluene (30 mL). 0.5M potassium hexamethyl disilazide (36.3 mL, 18.17 mmol) in toluene was added, the solution turned dark, and the reaction was exothermic. The brown solution was stirred overnight at ambient temperature. The reaction was quenched with saturated NH4Cl solution and diluted with EtOAc. The organic layer was washed with saturated NH4Cl solution, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica (5-50% EtOAc in heptane) to give Example 234A (1.188 g, 5.25 mmol, 43.4% yield) as a yellow liquid. MS (DCI+): m/z 244 (M+NH4). 1H NMR (300 MHz, DMSO-d6) delta 8.21 (t, J=8.0 Hz, 1H), 7.95 (d, J=4.7 Hz, 1H), 7.92 (d, J=4.5 Hz, 1H), 2.86-2.69 (m, 4H), 2.38-2.19 (m, 1H), 2.15-1.96 (m, 1H).

The synthetic route of 4426-11-3 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.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
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Reference of 6011-14-9,Some common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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.

Under nitrogen protection100 g (523 mmol) of 4-trifluoromethylnicotinic acid and 600 mL of toluene were placed in a three-neck reaction flask with a reflux condenser and a constant pressure dropping funnel, and 125 g (1.05 mol) of SOCl2 was slowly added to the reaction flask at 0 C. It was refluxed at 120 C for 2.5 hours. The contents of the reaction flask were concentrated, and after cooling, 600 mL of THF was added. 100 g (1.08 mol) of aminoacetonitrile hydrochloride and 600 mL of toluene were placed in the previous reaction flask, and the reaction flask was cooled to 0 C to maintain the temperature, and 190 g (1.88 mol) of Et 3 N was slowly added. The reaction flask was reacted at 25 C for 10 hours, and then most of the THF solution was removed under reduced pressure, and water and ethyl acetate were added for extraction.After drying and concentrating the organic phase, 112 g (488 mmol) of the solid of flonicamid was obtained.The yield was 93.4%.

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

Reference:
Patent; Shanghai Heteng Fine Chemical Co., Ltd.; Chen Sheng; Shi Guancheng; Meng Haicheng; (10 pag.)CN108191749; (2018); A;,
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These common heterocyclic compound, 630-18-2, name is Pivalonitrile, 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. Recommanded Product: 630-18-2

General procedure: To an ice cold solution of pivalonitrile (1f, 120 muL, 1.085 mmol) in Et2O (1.0 mL)was added an ethereal solution of 2-naphthylmagnesium bromide (2b, 0.75 M, 1.88mL, 1.410 mmol) and the reaction mixture was stirred at 60 C in a sealed tube for 2 h.After cooling to 0 C, the reaction mixture was treated with anhydrous MeOH (132muL), followed by the addition of CuBr2 (24.3 mg, 0.109 mmol) and anhydrous DMF(10.0 mL). The resulting reaction mixture was stirred at 80 C under an oxygenatmosphere for 6 h. Then the reaction was quenched by the addition of pH 9ammonium buffer solution and the organic materials were extracted with Et2O. Thecombined organic extracts were washed with water, and then with brine and driedover anhydrous MgSO4. The solvents were removed in vacuo and the resulting crudematerial was purified by flash column chromatography using hexane-EtOAc (90:10)to afford 2-naphthonitrile

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

Reference:
Article; Tnay, Ya Lin; Ang, Gim Yean; Chiba, Shunsuke; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1933 – 1943;,
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Adding a certain compound to certain chemical reactions, such as: 4426-11-3, name is Cyclobutanecarbonitrile, 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 4426-11-3, COA of Formula: C5H7N

Intermediate 371-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile; Lithium diisopropylamide (3.34 mL, 6.68 mmol), was added dropwise to a solution of cyclobutanecarbonitrile (0.417 g, 5.14 mmol) in THF (20 mL) at -78 C. under an argon atmosphere. The reaction mixture was stirred at -78 C. for 30 min, then was a solution of 4-bromo-1-(bromomethyl)-2-iodobenzene (see Caruso, A.; Tovar, J., D. J. Org. Chem. 2011, 76, 2227-2239., 2.51 g, 6.68 mmol) in THF (8 mL) slowly added dropwise and the reaction was allowed to reach r.t. The mixture was stirred for another 3 h and then quenched with water. The reaction mixture was partitioned between water and EtOAc, the organic layer was dried over MgSO4 and concentrated to give a crude product which was purified by flash chromatography (eluent: heptane/ethylacetae 12:1) to afford the title compound (1.71 g, 89% yield): 1H NMR (500 MHz, CDCl3) delta ppm 2.08-2.34 (m, 4H), 2.47-2.58 (m, 2H), 3.18-3.23 (m, 2H), 7.29 (s, 1H), 7.49 (dd, 1H), 8.03 (d, 1H); GC MS (EI) m/z 375 M

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; ASTRAZENECA AB; US2012/165347; (2012); A1;,
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Related Products of 4475-95-0, 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. 4475-95-0 name is 2-Amino-2-methylbutanenitrile, 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.

General procedure: To a mixture of carboxylic acid (1 mmol), EDC·HCl (1.2 mmol) and HOBt (1.2 mmol) in dry dichloromethane (10 mL) was added a mixture of amine (1 mmol) and triethyl amine (1.5 mmol) in dichloromethane (5 mL) at 0 C. The mixture was stirred at room temperature till the completion of reaction (judged by TLC). The reaction mixture was diluted with additional DCM (20 mL). The organic layer was washed with water, brine and dried (Na2SO4). Concentration and purification over silica gel (100-200 mesh) afforded the desired compound.

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

Reference:
Article; Sasmal, Pradip K.; Talwar, Rashmi; Swetha; Balasubrahmanyam; Venkatesham; Rawoof, Khaji Abdul; Neelima Devi; Jadhav, Vikram P.; Khan, Sanjoy K.; Mohan, Priya; Srinivasa Reddy; Nyavanandi, Vijay Kumar; Nanduri, Srinivas; Shiva Kumar; Kannan; Srinivas; Nadipalli, Prabhakar; Chaudhury, Hira; Sebastian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 16; (2011); p. 4913 – 4918;,
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