Tag: M.W=0-100

Electric Literature of 4426-11-3,Some common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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.

S nthesis of l-(5-bromo-pyridin-2-yl)-cyclobutanecarbonitrileTo a solution of lithium diisopropylamine (2.0 M in heptane/THF/ethylbenzene, 10 mL, 20.0 mmol) at -78 C is added R-4 (811 mg, 10.0 mmol). The reaction mixture is stirred at -78 C for 45 minutes, followed by the addition of R-3 (1.9 g, 8.0 mmol). The reaction mixture is allowed to warm to room temperature slowly, stirred for 16 hours, and heated at 70 C for 2 hours. The reaction mixture is allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with brine, dried with Mg2S04, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-100% EtOAc in heptane) to give the title intermediate 1-13

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
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Some common heterocyclic compound, 19295-57-9, name is 3-Hydroxy-2,2-dimethylpropanenitrile, molecular formula is C5H9NO, 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. category: nitriles-buliding-blocks

To a solution of 9j (0.33g, 1.96mmol) in ethanol (5mL) was added 50% aqueous hydroxylamine solution (0.39g, 5.88mmol), and the reaction mixture was then stirred at room temperature for 1h and evaporated in vacuo. The residue was purified using silica gel column chromatography (methanol/chloroform) to yield 10j (0.23g, 58%) as a colorless oil. 1H NMR (200MHz, CDCl3) delta 1.52-2.09 (m, 7H), 2.87-3.03 (m, 2H), 3.14-3.28 (m, 1H), 3.33-3.46 (m, 1H), 4.35 (br s, 2H), 4.71-4.90 (m, 1H); MS (ESI): m/z 202 [M+H]+, 224 [M+Na]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19295-57-9, its application will become more common.

Reference:
Article; Oka, Yusuke; Yabuuchi, Tetsuya; Oi, Takahiro; Kuroda, Shoichi; Fujii, Yasuyuki; Ohtake, Hidenori; Inoue, Tomoyuki; Wakahara, Shunichi; Kimura, Kayo; Fujita, Kiyoko; Endo, Mayumi; Taguchi, Kyoko; Sekiguchi, Yoshinori; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7578 – 7583;,
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Reference of 4426-11-3, The chemical industry reduces the impact on the environment during synthesis 4426-11-3, name is Cyclobutanecarbonitrile, I believe this compound will play a more active role in future production and life.

General procedure: l-(2-methylbenzyl)cyclobutanecarbonitrile[579] n-BuLi (0.018mol, 7.2ml, 2.5M) was added to a solution of diisopropylamine (1.7 g, 0.017 mol) in THF (15 mL) at -78C. After 5 minutes neat cyclobutancarbonitrile (1.2g, 0.015mol) was added and the mixture was stirred at -78 C for 1 hour. Then a solution of 1 -(bromomethyl)-2-methylbenzene (3.3 g, 0.018 mol) in THF (3 mL) was added and the mixture was stirred at -78 C for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic phase was concentrated and the residue was directly used to the next step without further purification. MS: m/z 186 (M+H)

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, Cyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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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. 151-18-8, name is 3-Aminopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

A. (S)-N-(2-Cyano-ethyl)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-Phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionamide. To a 3-neck round-bottom flask was added (S)-3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid (Example 1; 5.0 g, 9.9 mmol, 1.0 equiv), EDC (4.7 g, 24.7 mmol, 2.5 equiv) and HOBT (3.3 g, 24.7 mmol, 2.5 equiv) under nitrogen. N,N-Dimethylformamide (50 mL) was added, followed by 3-aminopropanenitrile (1.9 g, 24.7 mmol, 2.5 equiv) and diisopropylethylamine (6.8 mL, 39.6 mmol, 4.0 equiv). The reaction mixture was stirred overnight, then was diluted with ethyl acetate (200 mL), washed with 1 N HCl (100 mL), H2O (100 mL), 10% sodium bicarbonate (100 mL), H2O (100 mL) then brine (100 mL), and dried (sodium sulfate). The solvent was then removed under reduced pressure yielding the desired amide (5.35 g, 99%), which was used in the next step without purification. HPLC: Rt=7.89 (Method A). MS (ESI): mass calculated for C29H26Cl2N4O2, 532.14; m/z found, 533.3 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.31-7.30 (m, 2H), 7.23 (t, J=7.4 Hz, 1H), 7.19 (br s, 1H), 7.16-7.14 (m, 3H), 7.10 (d, J=7.4 Hz, 1H), 6.91 (dd, J=8.5, 2.2 Hz, 1H), 6.87 (d, J=9.0 Hz, 2H), 6.20 (s, 1H), 6.09 (t, J=6.0 Hz, 1H), 3.90 (dd, J=9.0, 6.0 Hz, 1H), 3.82 (s, 3H), 3.56-3.50 (m, 2H), 3.35-3.31 (m, 1H), 3.08 (dd, J=14.8, 6.0 Hz, 1H), 2.53-2.46 (m, 2H), 2.35 (s, 3H).

According to the analysis of related databases, 151-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); A1;,
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Synthetic Route of 630-18-2,Some common heterocyclic compound, 630-18-2, name is Pivalonitrile, molecular formula is C5H9N, 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.

Step 1: Synthesis of N-hydroxy-2,2-dimethyl-propionamidine (Intermediate 20, Table 4) The title compound is prepared from commercially available materials by those skilled in the art by adaptation of a patent reference (Neighbors et al, US 3,547,621). To a solution of hydroxylamine hydrochloride (6.80 g, 97.9 mmol) in water (15 mL) is added slowly a solution of potassium carbonate (6.15 g, 44.5 mmol) in water (10 mL) and 2,2-dimethyl propionitrile (6.25 g, 89.0 mmol) in ethanol (50 mL). The mixture is stirred at room temperature for 30 min then heated at reflux for 16 h. After this time, dichloromethane (75 mL) and water (50 mL) are added and the aqueous layer is extracted with dichloromethane (3 x 50 mL). The organic layers are combined, washed with brine (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title compound as a white solid (6.15 g, 60%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.21 (9 H, s), 4.57 (2 H, br. s.), 9.15 (1 H, br. s.).

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

Reference:
Patent; Boehringer Ingelheim International GmbH; Boehringer Ingelheim Pharma GmbH & Co. KG; EP2418207; (2012); A1;,
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Synthetic Route of 20249-16-5, 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. 20249-16-5 name is 3-Oxocyclobutanecarbonitrile, 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.

A solution of 3-oxocyclobutane-1-carbonitrile* (CAS: 20249-16-5, 14.5 g, 152 mmol) in THF (250 mL) was added to a mixture of (EtO)2P(O)CH2CN (31.1 g, 175 mmol), LiBr (19.9 g, 229 mmol) and TEA (30.9 g, 305 mmol) in THF (300 mL) at about 25 C. After about 16 hrs, the mixture was filtered and the filtrate was concentrated. The residue was purified by chromatography to afford the title compound as a light yellow oil (16.01 g, 89%).1H NMR (400 MHz, CD3CN) delta: 5.38 (s, 1H), 3.30-3.43 (m, 2H), 3.16-3.30 (m, 3H).LCMS m/z=119.1 [MH]+

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

Reference:
Patent; Pfizer Inc.; BROWN, Matthew Frank; DERMENCI, Alpay; FENSOME, Andrew; GERSTENBERGER, Brian Stephen; HAYWARD, Matthew Merrill; OWEN, Dafydd Rhys; WRIGHT, Stephen Wayne; XING, Li Huang; YANG, Xiaojing; (67 pag.)US2017/240552; (2017); A1;,
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Synthetic Route of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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.

A mixture of lithium (Z)-l-(5-bromo-2-methoxypyridin-3-yl)-2- (dimethoxvphosphoryl)ethenolate (2.0 g, 5.8 mmol) and 3-oxocyclobutanecarbonitrile (1.1 g, 12 mmol) in p-dioxane (6 ml) was heated at 1200C by Microwave in Ih. The mixture was cooled, taken up in H2O, extracted with EtOAc (3x), dried over MgSO4, concentrated to provide the title compound. MS (m+1): 307.0.

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

Reference:
Patent; AMGEN INC.; WO2008/147544; (2008); A1;,
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Synthetic Route of 6011-14-9, A common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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.

Toluene (5 mL)(2,3-b] pyrazin-7-yl) aniline (36 mg, 0.12 mmol) was added to a solution of 4- (2- (1-methyl-1H-pyrazol-4-yl) -5H-pyrrolo [Triphosgene (33 mg, 0.11 mmol)Add two drops of triethylamine,110 reflux reaction 5h,The reaction solution was cooled to room temperature,Aminoacetonitrile hydrochloride (28 mg, 0.30 mmol) was added,Triethylamine (100 mg, 0.10 mmol)Stirred at room temperature for 12 h,Reaction by adding silica gel, direct spin dry mix,Column separation (dichloromethane / methanol (v / v) = 15/1)35 mg of a white solid was obtained in a yield of 75.8%.

The synthetic route of 6011-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
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Related Products of 2469-99-0, 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. 2469-99-0 name is 3-Oxobutanenitrile, 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.

Porphyrin 16 (40mg, 0,026mmol) and 2-cyanoacetic acid 10 (10mg, 0.11mmol) were dissolved in a THF solution (5mL). Then, piperidine (8muL) was added and the reaction mixture was heated at 65C for 24 h under N2. The resulting solution was evaporated to dryness under vacuum. Finally, the crude residue was purified by column chromatography over silica gel using CH2Cl2/MeOH as an eluent (in a 98:2 ratio) to obtain ZnP-3DoH-CNCOOH in 78% yield (28mg). 1H NMR (500 MHz, CDCl3): delta=8.83 (d, J=3.7Hz, 2H), 8.78 (sb, 4H), 8.72 (d, J=4.2Hz, 2H), 8.24 (d, J=6.9Hz, 2H), 7.64 (m, 5H), 6.97 (m, 6H), 3.79 (m, 12H), 0.92 (m, 12H), 0.50 (m, 36H), 0.27 (m, 18H) ppm. MS (MALDI-TOF): calcd. for C84H102N5O8Zn [M + H]+ 1372.7020; found 1372.701. UV-Vis in THF [lambdamax/nm (epsilon/mM-1 cm-1)]: 422 (399.7), 550 (16.6).

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

Reference:
Article; Nikolaou, Vasilis; Charisiadis, Asterios; Chalkiadaki, Sofia; Alexandropoulos, Ioannis; Pradhan, Sourava C.; Soman, Suraj; Panda, Manas K.; Coutsolelos, Athanassios G.; Polyhedron; vol. 140; (2018); p. 9 – 18;,
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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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Oxocyclobutanecarbonitrile

Compound 10-2 (8.0g, 84.21mmol) was dissolved in DCM (80mL) at 0C, added DAST (27g, 0.168mol). The reaction mixture was stirred overnight at room temperature, and the end of the reaction was monitored by TLC (petroleum ether/ethyl acetate = 3: 1). Ice water was added to the reaction solution, extracted with DCM, washed with saturated brine, and then dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure and purified by column chromatography (petroleum ether/ethyl acetate = 150: 1-30:1) to give the crude Compound 10-3 (8.1g) as a brown oil.

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP Biosciences Co., Ltd.; ZHANG, Hui; DONG, Yanyan; EP2738156; (2014); A1;,
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