Tag: M.W=100-200

6775-78-6, A common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, molecular formula is C6H4ClN3, 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.

[0517] Synthesis of methyl imidazo[l,2-b]pyridazine-6-carboxylate: [0518] To a stirred solution of 6-chloroimidazo[l,2-b]pyridazine (2.0 g, 13.15 mmol) in ACN:MeOH (60 mL, 1 : 1) under N2 bubbling atmosphere were added BINAP (818 mg, 1.31 mmol), Pd(ACN)2Cl2 (341 mg, 1.31 mmol) and Et3N (1.60 g, 15.78 mmol) in a steel bomb. The resultant reaction mixture was agitated under CO atmosphere (150 psi) at 100 C for 16 h. After full consumption of starting material by TLC, the reaction was diluted with water and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford imidazo[l,2-b]pyridazine-6-carboxylate (1.3 g, 65%) as brown solid. 1H-NMR (DMSO-d6, 500 MHz): delta 8.51 (s, 1H), 8.27 (d, 1H), 7.94 (s, 1H), 7.72 (d, 1H), 3.97 (s, 3H); LC-MS: 91.14%; 178 (M++l) (column; X- bridge C-18, (50×3.0 mm, 3.5mu); RT 2.28 min. 5mM NH4OAc: ACN; 0.8 ml/min); TLC: 70% EtOAc/Hexane (Rf: 0.5).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
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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 39989-43-0 as follows. 39989-43-0

Step 8 Preparation of 8-hydroxy-6-methyl-[1,6]naphthyridine-7-carboxylic Acid 3,5-dichloro-benzylamide (124H) A mixture of 124G (150 mg, 0.64 mmol), 3,5-dichlorobenzylamine (153 mg, 0.87 mmol) and aluminum chloride (27 mg, 0.20 mmol) in toluene (8 mL) was refluxed for 4 h under nitrogen. After cooling to room temperature, the reaction mixture was treated with aqueous saturated NaHCO3 solution and ethylenediaminetetraacetic acid (1 g, 3.4 mmol) to pH 7. The mixture was extracted with chloroform four times. The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by preparative reverse-phase HPLC to give 124H. 1H NMR (400 MHz, DMSO) delta 13.2 (s, 1H), 9.73 (t, 1H), 9.15 (dd, 1H), 8.64 (dd, 1H), 7.83 (dd, 1H), 7.52 (s, 1H), 7.44 (s, 2H), 4.57 (d, 2H), 2.85 (s, 3H).

According to the analysis of related databases, 39989-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); A1;,
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A common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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. 13078-79-0.

Example 23; 3-[5,6-Bis(methyloxy)-2-pyridinyll-Lambda/-[2-(3-chlorophenylkthyll-2,4-dioxo-l,2,3,4- tetrahydrothieno[3,2-Patent; GLAXOSMITHKLINE LLC; SCHULZ, Mark, James; WANG, Younghui; GHERGUROVICH, Jonathan M.; WO2010/59555; (2010); A1;,
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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 344-19-4 as follows. 344-19-4

General procedure: A solution of 2,4,6-trisubstitutedphenylamine (10, 0.8 mmol) in pyridine (10 mL) was added to the flask containingt he crude acyl chloride 8 (0.8 mmol) which was prepared from the procedure described above, and the mixture was refluxed for 3-5 h. After cooling down, the mixture was poured into water (50 mL) and extracted with ethyl acetate (3¡Á 15 mL). The extracts were combined and washed with hydrochloric acid (2 ¡Á 10 mL) and brine, successively. The organic phase was dried over anhydrous Na2SO4. After solvent removal, the residue was further purified by recrystallization from ethanol to afford the title compound 12(a-c) as a solid.

According to the analysis of related databases, 344-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Baolei; Wang, Hongxue; Liu, Hang; Xiong, Lixia; Yang, Na; Zhang, Yan; Li, Zhengming; Chinese Chemical Letters; vol. 31; 3; (2020); p. 739 – 745;,
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363-51-9, name is 2-Chloro-6-fluoroaniline, belongs to chlorides-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. 363-51-9

To a solution of 392 mg (0.890 mmol [calculation value with the purity defined as 100%]) of ethyl 5-(chioro- carbonyl)-6,6-dimethyl-3-[1 -(trimethylsilyl)cyclobutanecarboxamido]-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)- carboxylate synthesized in the same way as in Reference Example 4 in 2.5 ml of 1,4-dioxane, 0.60 ml (3.4 mmol) of DIPEA and 807 mg (5.54 mmol) of 2-chloro-6-fluoroaniline were added at room temperature in a nitrogen atmosphere, reacted at 1000 C. for 1 hour with stirring, and then reacted at 130 C. for 0.5 hours and further at 150 C. for 2 hours in a microwave reaction apparatus. Subsequently, 0.50 ml (4.6 mmol) of N,N-dimethylethane-1 ,2-diamine was added thereto at room temperature and then reacted at room temperature for 1.5 hours with stirring.10718] After completion of the reaction, ethyl acetate was added to the reaction solution, followed by washing with a 5% aqueous potassium bisulfate solution. After separation into an organic layer and an aqueous layer, the aqueous layer was subjected to extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 2, DIOL silica gel, elution solvent: n-hexane:ethyl acetate=80:20-65:35-50:50 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 2, silica gel, elution solvent: dichloromethane_methanol=100:0 99:1-98:2-97:3 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure to obtain a white solid (approximately 70 mg). The obtained solid was subjected to preparative column chromatography (apparatus 3, ODS silica gel, elution solvent: acetonitrile: 1 mM aqueous dipotassium biphosphate solution=50:50-80:20 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure, followed by the distilling oil of acetonitrile. The obtained concentration residue was subjected to extraction three times with ethyl acetate, and subsequently, the whole organic layer was washed with saturated saline, then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained concentration residue was dissolved in ethyl acetate, then n-hexane was added thereto, and the deposited solid was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain 57.1 mg of the title compound (yield: 13% [calculation value with the purity of the starting material defined as 100%]) as a white solid.10719] Mass spectrum (CI, mlz): 478 [M+1].10720] ?H-NMR spectrum (400 MHz, DMSO-d5) oe: 12.27 & 11.69 (br s, total 1H), 9.64-9.54 (m, 1H), 8.09-7.89 (m, 1H), 7.38-7.19 (m, 3H), 4.69-4.52 (m, 2H), 2.56-2.39 (m, 2H), 2.28-2.13 (m, 2H), 1.93-1.73 (m, 2H), 1.70-1.54 (m, 6H), 0.15-0.04 (m, 9H).

Statistics shows that 363-51-9 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-6-fluoroaniline.

Reference:
Patent; UBE INDUSTRIES, LTD.; IWASE, Noriaki; AGA, Yasuhiro; USHIYAMA, Shigeru; KONO, Shigeyuki; SUNAMOTO, Hidetoshi; MATSUSHITA, Takashi; OGI, Sayaka; UMEZAKI, Satoshi; KOJIMA, Masahiro; ONUMA, Kazuhiro; SHIRAISHI, Yusuke; OKUDO, Makoto; KIMURA, Tomio; (165 pag.)US2018/186818; (2018); A1;,
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13078-79-0, The chemical industry reduces the impact on the environment during synthesis 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, I believe this compound will play a more active role in future production and life.

At 0C, methyl chloroformate (4.6 g, 48 mmol) was added drop wise to a solution of 2-(3-chloro-phenyl)-ethylamine (5.0 g, 32 mmol) and Et3N (6.4 g, 64 mmol) in DCM (100 mL).After the addition, the mixture was stirred at room temperature for 0.5 hours. The organic layer was washed with water (3 x 30 mL), iN HC1 (20 mL) and brine (30 mL), dried over anhy. Na2SO4, filtered and concentrated in vacuo. After vacuum drying, the title compound was obtained (6.49 g, 95%) as a white solid. MS: 214.1 (M+H).

The chemical industry reduces the impact on the environment during synthesis 2-(3-Chlorophenyl)ethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LI, Dongbo; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; WU, Jun; ZHOU, Mingwei; WO2014/191336; (2014); A1;,
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108-37-2, 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 108-37-2 as follows.

General procedure: Na2CO3 (212 mg, 2 mmol), 4-chloronitrobenzene (1 mmol) and styrene (1.5 mmol) were added successively into a dried Schlenk tube under nitrogen. Then the DMA (0.1mL) solution of DADPP (0.002mmol) and [Pd(C3H5)Cl]2 (0.0005mmol), which was reacted at 100C for 10 min prior to use, was added into the mixture. The reaction was performed at 130C. At the end of reaction, the mixture solution was extracted with ethyl acetate (3¡Á5 mL). Combined organic phase was washed with brine (3¡Á5mL) and dried over MgSO4. The dried solution was filtered and purified with silica gel chromatography (petroleum ether 60-90C) to give a corresponding product.

According to the analysis of related databases, 1-Bromo-3-chlorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Zhi-Jie; Wang, Wei; Zhou, Rong; Zhang, Lei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 57; (2013); p. 14 – 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. 83121-15-7, name is 3,5-Dichloro-2,4-difluoroaniline, A new synthetic method of this compound is introduced below., 83121-15-7

To a mixture of 3,5-dichloro-2,4-difluoroaniline (5.0 g), an aqueous 57% solution of hydroiodic acid (20 ml) and water (20 ml), copper iodide (1.92 g) was added. The reaction liquid was maintained at 30C or less in a water bath.To the reaction mixture was added dropwise a water solution (2 mL) of sodium nitrite ( 1.74 g). The reaction mixture was stirred for 10 minutes, maintained at 30C or less in a water bath. To the reaction mixture was added dropwise a water solution (2 mL) of sodium nitrite (1.74 g), again. The reaction mixture was further stirred for 10 minutes, maintained at 30C or less in a water bath. To the reaction mixture was added dropwise a water solution (2 mL) of sodium nitrite (1.74 g), again. t-Butyl methyl ether was added and the mixture was washed with water and with an aqueous solution of sodium sulfite and brine, and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (n- hexane) to obtain l,3-dichloro-2,4-difluoro-5-iodobenzene (6.0 g). i-NMR (CDC13) delta: 7.6-7.75 (1H, m).

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; BAYER CROPSCIENCE AG; MIHARA, Jun; HATAZAWA, Mamoru; YAMAZAKI, Daiei; KISHIKAWA, Hidetoshi; DOMON, Kei; WATANABE, Hidekazu; SASAKI, Norio; MURATA, Tetsuya; ARAKI, Koichi; SHIMOJO, Eiichi; ICHIHARA, Teruyuki; ISHIKAWA, Tadashi; SHIBUYA, Katsuhiko; GOeRGENS, Ulrich; BRUeCHNER, Peter; FISCHER, Reiner; JANSEN, Johannes-Rudolf; KAPFERER, Tobias; MAECHLING, Simon; MAUE, Michael; VOERSTE, Arnd; WO2012/35011; (2012); 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. 626-43-7, name is 3,5-Dichloroaniline, This compound has unique chemical properties. The synthetic route is as follows., 626-43-7

Benzoyl acetone (0.165 g, 1.017 mmol) was dispersed over Montmorillonite K-10 catalyst (1.5 g) and a mixture of 3.5-dichloroaniline (0.552 g, 3.407 mmol) with 20 ml THF was added dropwise, while stirring. The reaction was stirred at room temperature for 48 h. The catalyst was removed by filtration and the solvent was removed on a rotary evaporator, yielding a dark red oil.Yield 93%. Colour: dark red. UV: lambdamax 359 nm, epsilonmax 29453 mol-1dm3cm-1 (CH3CN), 1H NMR (300 MHz, CDCl3, 25C):delta 7.91-7.89 ppm (d, aromatic, 2H); 7.54-7.44 ppm (m, aromatic,3H); 6.75-6.74 ppm (t, aromatic, 1H); 6.56 ppm (d, aromatic, 2H);6.20 ppm (s, CH, 1H); 2.22 ppm (s, CH3, 3H).

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; Ngake, Tankiso Lawrence; Potgieter, Johannes Hermanus; Conradie, Jeanet; Electrochimica Acta; vol. 296; (2019); p. 1070 – 1082;,
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29671-92-9, 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 29671-92-9 as follows.

Example 312-amino-N-hydroxy-4-oxo-3,4-dihydroquinazoline-7-carboxamide; Compound I-199 Step 1: methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate; Intermediate-12Into a round bottom flask was added dimethyl 2-aminoterephthalate (1.0 g, 4.8 mmol) mixed with carbamimidic chloride-HCl (1.10 g, 9.6 mmol) and dimethyl sulfone (4.5 g, 47.8 mmol). The reaction mixture was heated to 150 C. and stirred overnight. The mixture was cooled to rt, water added and the solid was filtered. The solid was then washed with acetic acid to afford methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate (1.0 g, 95%). LC-MS: (FA) ES+220

According to the analysis of related databases, 29671-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2012/94997; (2012); A1;,
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