Tag: M.W:200-300

Reference of 69422-72-6 ,Some common heterocyclic compound, 69422-72-6, molecular formula is C6H2Cl3NO2, 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.

A solution of the product of EXAMPLE IOC (6.0 g, 26.5 mmol) in dichloromethane (150 mL) was treated at 0C with 2 drops of Nu,Nu-dimethylformamide. Oxalyl chloride (6.73 g, 53 mmol) was added dropwise over 30 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. A solution of the acid chloride (4.5 g, 18.4 mmol) in 60 mL of dry dichloromethane was added dropwise over 1 hour to a solution of tert-butyl 2-aminoethylcarbamate (5.9 g, 36.8 mmol) and triethylamine (3.7 g, 36.8 mmol) in 40 mL of dry dichloromethane at 0C and stirring was continued for 2 hours. The mixture was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 390 (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,69422-72-6, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas, Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97479; (2012); A1;,
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Related Products of 55304-83-1, Adding some certain compound to certain chemical reactions, such as: 55304-83-1, name is 2,6-Dibromonicotinaldehyde,molecular formula is C6H3Br2NO, 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 55304-83-1.

Reference Example 15 2,6-Dibromonicotinic acid To a solution of 2,6-dibromo-3-formylpyridine (0.3 g) in tert-butanol (12 mL) – water (1 mL) were added sodium dihydrogen phosphate (0.14 g), 2-methyl-2-butene (0.32 g) and a solution of sodium chlorite (0.36 g) in water (2 mL) successively at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was poured into water. The mixture was acidified by adding 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (0.28 g).

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. 55304-83-1, 2,6-Dibromonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
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Pyridine | C5H5N – PubChem

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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H3ClN2O4

To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60°C until the evolution of gaz has ended. Then it is stirred at 80°C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0°C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50°C to give 27.6 g (13.7 mmol/52 percent) of the title compound as a light yellow solid with a melting point of 78°C (dichloromethane/methanol).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTANA PHARMA AG; WO2005/77947; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, 89415-54-3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

6-Bromo-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridineTo a solution of 5-bromo-N2-methylpyridine-2,3-diamine (720 mg, 3.56 mmol) inH2S04(1.90 muIota_, 35.6 mmol) at RT, NaN02(246 mg, 3.56 mmol) was added. The reaction mixture was stirred for 1 h after which time water was added to quench the reaction. EtOAc was added, and the layers were separated. The aqueous layer was extracted once with EtOAc, and the combined organic layers were washed once with brine. The organic layer was concentrated to give 694 mg (91 %) of the title compound. LC-MS m/z 212.8, 214.8 (M+H)+, 0.66 (ret. time).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

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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Electric Literature of 960289-03-6 , The common heterocyclic compound, 960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, 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.

Preparation 29; 2-(4-Chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one; Combine 2-bromo-6H-thieno[2,3-c]pyridin-7-one (25.0 g, 108.7 mmol), A- chlorophenylboronic acid (18.7 g, 119.5 mmol), sodium carbonate (23.5 g, 217.3 mmol), ethanol (121 mL), 1 ,2-dimethoxyethane (604 mL), and water (121 mL). Purge the mixture with nitrogen for 20 min. Add tetrakis(triphenylphosphine)palladium (3.77 g, 3.26 mmol). Heat the reaction mixture at 85 0C overnight. Allow the reaction to cool to RT. Reduce the reaction solvent volume to half on a rotory evaporator. Filter the mixture with water (2 x 400 mL), ether (400 mL), and ethylacetate (20 mL) and dry the solids in vacuo at 40 0C to give 25.4 g (89%) of the title compound. LC-MS/ES m/z (35Cl) 262.0 [M+H]+.

The synthetic route of 960289-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, 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, Formula: C10H11BrClNO2, blongs to pyridine-derivatives compound. Formula: C10H11BrClNO2

Example 14A methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylate Methyl 4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylate (500 mg), EXAMPLE 1D (572 mg), and triethylamine (0.545 mL) in anhydrous dimethylsulfoxide (6.5 mL) was heated to 100 C. overnight, and the mixture was then cooled to room temperature. The reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (15 mL) and ethyl acetate (15 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2*15 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 0-40% ethyl acetate/hexanes to provide the title product.

The synthetic route of 1235036-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
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Application of 717843-51-1, Adding some certain compound to certain chemical reactions, such as: 717843-51-1, name is 3-Bromo-2-methoxy-4-methylpyridine,molecular formula is C7H8BrNO, 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 717843-51-1.

To a pressure tube was added 3-bromo-2-methoxy-4-methylpyridine (396 mg, 1.96 mmol), bis(pinacolato)diboron (597 mg, 2.35 mmol), Pd(dppf)2Cl2 (143 mg, 0.20 mmol), potassium acetate (384 mg, 3.92 mmol) and 1,4-dioxane (15 mL). The mixture was stirred at 95 C. for 4 hours. The residue was purified by silica gel flash chromatography (petroleum ether/ethyl acetate, 4:1) to give 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (250 mg, 51% yield) as a colourless oil. LCMS (ESI): [M+H]+=249.3.

According to the analysis of related databases, 717843-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyridine – Wikipedia,
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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. 1072438-56-2, name is Methyl 6-(aminomethyl)nicotinate hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Methyl 6-(aminomethyl)nicotinate hydrochloride

[0112j To a solution of methyl 6-(aminomethyl)nicotinate hydrochloride (0.4 g, 1.67 mmol) in dichloromethane (20 mL) was added triethylamine (1.2 mL, 8.37 mmol)) followed by 4- fluoro-3-chlorobenzenesulfonyl chloride (0.24 ml, 1.67 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by silica gel column chromatography, using 40% ethyl acetate in hexane to afford the title compound methyl 6-((3 -chloro-4-fluorophenylsulfonamido)methyl)nicotinate (0.22 g, 37%yield) as a brownish solid. Calculated M+H: 359.02; Found M+H: 359.1.

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, 1072438-56-2, Methyl 6-(aminomethyl)nicotinate hydrochloride.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59782-86-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.59782-86-4, name is 2-Chloro-5-iodonicotinic acid, molecular formula is C6H3ClINO2, molecular weight is 283.45, as common compound, the synthetic route is as follows.

The mixture of 19 (29.8 g, 107 mmol), DMF (1.5 mL) and SOCl2 (78 mL, 10 eq.) was stirred at 70 C for 4 h. The mixture was concentrated in vacuo and diluted with DMF (6 mL). Water (90 mL) was slowly added to the mixture and then satd NaHCO3 aq (200 mL) was slowly added. The mixture was acidified to pH 4 by 1 N HCl (55 mL) and stirred at room temperature for 2 h and at 0 C overnight. After filtration, the solid was washed with water and dried in vacuo to yield a crude mixture of 2-chloro-5-iodonicotinic acid as a pale yellow solid (27 g). The solid was suspended in CHCl3 (135 mL) and SOCl2 (13.9 mL) and the suspension was stirred at reflux for 0.5 h. DMF (0.5 mL) and SOCl2 (27.8 mL) were added to make a clear solution and the mixture was stirred at reflux for 1.5 h, then cooled and concentrated in vacuo. EtOH (135 mL) was slowly added to the residue at 0 C and the mixture was stirred at 0 C for 15 min. and at room temperature for 30 min. The mixture was concentrated in vacuo and partitioned between AcOEt (270 mL) and satd NaHCO3 aq (135 mL). The aqueous phase was extracted with AcOEt (135 mL) and the combined organic phase was washed with brine, dried over Na2SO4 and filtered. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (AcOEt/n-hexane; 0:100 to 20:80) to yield 20 as a white solid (27.25 g, 95%). 1H NMR (400 MHz, CDCl3) delta = 8.70 (d, J = 2.0 Hz, 1H), 8.41 (d, J = 2.0 Hz, 1H), 4.42 (q, J = 7.2 Hz, 2H), 1.42 (t, J = 7.2 Hz, 3H); MS (ESI+) 311.9 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 59782-86-4, I believe this compound will play a more active role in future production and life.

Reference:
Article; Takahashi, Bitoku; Funami, Hideaki; Iwaki, Takehiko; Maruoka, Hiroshi; Shibata, Makoto; Koyama, Makoto; Nagahira, Asako; Kamiide, Yoshiyuki; Kanki, Satomi; Igawa, Yoshiyuki; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4792 – 4803;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 39856-57-0, name is 2,6-Dibromopyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 39856-57-0

Synthesis of 6-bromo-2-methoxypyridin-3-amine To a stirred solution of 2, 6-dibromopyridin-3-amine (38 g, 0.188 mol) in 1,4-dioxane (400 mL) under an argon atmosphere was added sodium methoxide (70.55 g, 1.30 mol) at room temperature. The reaction mixture was stirred at reflux for 8 h. After consumption of the starting material (monitored by TLC), the reaction mixture was quenched with ice cold water (200 mL) and extracted with EtOAc (3*200 mL). The combined organic extracts were washed with cold water (2*100 mL), dried over sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography using 10% EtOAc:hexanes to afford 6-bromo-2-methoxypyridin-3-amine (13 g, 42%) as a brown solid. 1H-NMR (CDCl3, 400 MHz): delta 6.87 (d, 1H), 6.76 (d, 1H), 4.01 (s, 3H), 3.75 (br s, 2H); TLC: 20% EtOAc:hexane (Rf: 0.5).

With the rapid development of chemical substances, we look forward to future research findings about 39856-57-0.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
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Pyridine | C5H5N – PubChem