Tag: M.W:100-200

Electric Literature of 52334-51-7, 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. 52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Step 1. 6-methyl[1,3]oxazolo[5,4-b]pyridine-2(1H)-thione3-Amino-5-methylpyridin-2-ol (0.21 g, 1.7 mmol) was dissolved in THF (5 mL), and 1,1′-thiocarbonyldiimidazole (0.48 g, 2.7 mmol) was added. The mixture was stirred at RT for 20 min. The reaction was diluted with water, treated with 1N HCl to adjust the pH to the range of 4-5. The product was then extracted with ethyl acetate, the extracts were washed with brine, and dried over sodium sulfate, filtered and concentrated to afford the product, used without further purification in the following step. LCMS (M+H)+: m/z=167.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52334-51-7, 3-Amino-5-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1083197-78-7, 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. 1083197-78-7, name is 4-(Trifluoromethyl)nicotinaldehyde, molecular formula is C7H4F3NO, The 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 50-mL round-bottom flask was charged with 5-cyanopyridin-3-yl (R)-2-methylpiperazine-1-carboxylate (179 mg, 0.727 mmol, 1.20 equiv), 4-(trifluoromethyl)pyridine-3-carbaldehyde (106 mg, 0.606 mmol, 1.00 equiv), triethylamine (184 mg, 1.82 mmol, 3.00 equiv), and 1,2-dichloroethane (10 mL). The mixture was stirred for 1 hour at room temperature prior to addition of sodium triacetoxyborohydride (386 mg, 1.82 mmol, 3.00 equiv). The reaction was stirred overnight at room temperature and quenched with water (30 mL). The resulting solution was extracted with dichloromethane (2*50 mL) and the organic layers were combined, washed with brine (2*30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product (300 mg) was purified by preparative HPLC to afford 94.9 mg (39% yield) of 5-cyanopyridin-3-yl (R)-2-methyl-4-((4-(trifluoromethyl)pyridin-3-yl)methyl)piperazine-1-carboxylate as a yellow oil. 1H NMR (300 MHz, Chloroform-d) delta 9.02 (s, 1H), 8.71-8.73 (m, 2H), 8.64 (s, 1H), 7.84 (s, 1H), 7.54 (d, J=5.1 Hz, 1H), 4.41 (br, 1H), 3.99-4.03 (m, 1H), 3.73 (s, 2H), 3.48 (br, 1H), 2.84-2.87 (m, 1H), 2.69-2.73 (m, 1H), 2.42-2.47 (m, 1H), 2.01-2.31 (m, 1H), 1.41-1.42 (m, 3H). LCMS (ESI, m/z): 406 [M+H]+.

According to the analysis of related databases, 1083197-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; CISAR, Justin S.; DUNCAN, Katharine K.; FENG, Yu; WIENER, John J.M.; WEBER, Olivia D.; (79 pag.)US2018/256566; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 97N-((ls,4s)-4-(2-(4′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-3′-hydroxybiphenyl-3- yloxyJ-S-fluoronicotinamidoJcyclohexylJpyrazolo [ 1 ,5-a] pyridine-2-carboxamide To a solution of pyrazolo[l,5-a]pyridine-2-carboxylic acid (30.8 mg, 0.19 mmol) in acetonitrile (3 mL) was added DIPEA (0.066 mL, 0.38 mmol). To this mixture was then added HATU (72.3 mg, 0.19 mmol). The mixture was stirred at RT for 10 min before it was added to a solution of N-((ls,4s)-4-aminocyclohexyl)-2-(4′-(((3S,5R)-3,5-dimethylpiperazin- l-yl)methyl)-3′-hydroxybiphenyl-3-yloxy)-5-fluoronicotinamide, hydrochloride (125 mg, 0.19 mmol) and DIPEA (0.066 mL, 0.38 mmol) in acetonitrile (3 mL). The mixture was stirred at RT overnight. 1 mL water and 1 mL acetic acid was then added to the mixture before being purified using reverse phase preparative HPLC (eluent = TFA(aq)/MeCN). The appropriate fractions were combined and evaporated to give a residue. This was triturated with ether to give the title compound as a solid which was isolated by filtration and dried overnight under vacuum at 400C. Yield: 96 mg 1H NMR (400 MHz, CD3OD) delta 8.48 (d, J = 7.4 Hz, IH), 8.43 (d, J = 7.2 Hz, IH), 8.12 (d, J = 3.1 Hz, IH), 8.06 (dd, J = 7.9, 3.1 Hz, IH), 7.66 (d, J = 9.0 Hz, IH), 7.51 – 7.43 (m, 2H), 7.40 – 7.37 (m, IH), 7.25 – 7.17 (m, 3H), 7.10 – 7.07 (m, 2H), 6.97 – 6.93 (m, 2H), 4.17 – 4.11 (m, IH), 4.07 (s, IH), 4.04 – 3.99 (m, IH), 3.58 – 3.51 (m, 2H), 3.45 – 3.40 (m, 2H), 2.64 (t, J = 12.6 Hz, 2H), 1.92 – 1.70 (m, 8H), 1.31 (d, J = 6.4 Hz, 6H). MS: [M+H]+=692.2 (calc=692.336) (MultiMode+)

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, The 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.

N-[4-(5-Cyano-2-methoxy-pyridin-3-yl)-benzyl]-2-trifluoromethoxy-benzenesulfonamide To a solution of 4-aminomethylphenylboronic acid hydrochloride (2.0 g, 13.2 mmol) in methanol (20 ml) was added di-tert-butyl dicarbonate (3.16 g, 15.5 mmol) and sodium bicarbonate (3.32 g, 19.8 mmol). The mixture was sonicated for 4 h then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give (4-bromo-benzyl)-carbamic acid tert-butyl ester (1.8 g, 13.2 mmol, 100%) as a white solid. To 6-chloro-nicotinonitrile (15 g, 0.11 mol) under argon atmosphere was added 25% sodium methoxide in methanol (11.7 g, 0.22 mol) and the mixture heated under reflux for 20 h. The methanol was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give 6-methoxy-nicotinonitrile (17.0 g, 0.13 mol, 117%) as a white solid. To 6-methoxy-nicotinonitrile (13.2 g, 99 mmol) in acetic acid (32 ml) was added sodium acetate (8.1 g, 99 mmol). The mixture was stirred and a solution of bromine (31.5 g, 197 mmol) in acetic acid (32 ml) added. The mixture was heated to 80 C. for 48 h. The reaction mixture was poured into water and extracted with diethyl ether. The organic phase was washed with 4M aqueous sodium hydroxide solution, 5% sodium thiosulfate solution, dried over anhydrous potassium carbonate and the solvent was evaporated to give 5-bromo-6-methoxy-nicotinonitrile (11.9 g, 56 mmol, 57%). To a solution of 2-methoxy-5-cyanopyridine-3-boronic acid (1.0 g, 4.0 mmol) in 1,2-dimethoxyethane (10 ml) was added (4-bromo-benzyl)-carbamic acid tert-butyl ester (0.42 g, 2.0 mmol), tetrakis(triphenylphosphine)palladium (0) (114 mg, 0.1 mmol) and 2M aqueous sodium carbonate (1 ml, 2.0 mmol). The reaction was heated to 150 C. for 10 min in a microwave over. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic phase was washed with water, then brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified on silica gel eluting with 5:1 heptane/ethyl acetate to give [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester as a white solid (0.5 g, 1.47 mmol, 37%). To a solution of [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester (0.5 g, 1.5 mmol) in dichloromethane (5 ml) at 0 C. was added trifluoroacetic acid (5 ml, 28 mmol). The reaction mixture was stirred for 30 min at 0 C. before the solvent was evaporated and the residue purified on a SCX column (eluted with 2M ammonia in methanol) to give 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile as a clear glass (0.39 g, 1.6 mmol, 107%). To a solution of 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile (57.3 mg, 0.24 mmol) in dichloromethane (2 ml) was added triethylamine (73.0 mg, 0.72 mmol) and 2-(trifluoromethoxy)benzenesulfonyl chloride. The reaction mixture was agitated for 20 hours and the solvent evaporated under reduced pressure. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (19.1 mg, 0.04 mmol, 17%). 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, 1H), 8.47 (t, 1H), 8.15 (d, 1H), 7.90 (m, 1H), 7.73 (m, 1H), 7.45-7.55 (m, 4H), 7.31 (d, 2H), 4.19 (d, 2H), 3.96 (s, 3H) ppm; MS (ESI) m/z: 464.3 [M+H]+.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; N.V. Organon; Pharmacopeia Drug Discovery Inc.; US2007/149577; (2007); A1;,
Pyridine – Wikipedia,
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. 327056-62-2, name is 2-Cyano-5-fluoropyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3FN2

Example 32.2-(6-Fluoro-imidazo[l ,5-a]pyridin-l -yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3- cyano-azetidin- 1 -yl)- 1 -methyl-2- xo-ethyl]-amideStep 1(5 -Fluoro-pyridin-2-yl)-meth lamineIn a Parr pressure bottle, 2-cyano-5-fluoropyridine (2.0 g, 16.4 mmol) was dissolved in ethanol (60 ml). Palladium on carbon, 10% Pd (wet) (574 mg, 5.39 mmol) was added followed by cone. HC1 (4.6 ml, 56.0 mmol). The bottle was placed on a Parr hydrogenator and shaken for 3.5 h under a 45 psi hydrogen atmosphere. The reaction mixture was filtered over Celite and rinsed with methanol. The filtrate was concentrated to a light yellow solid. The solid was taken up in dichloromethane, cooled to 0C, and basified with saturated aqueous NaHC03. The aqueous layer was extracted with dichloromethane (3x) and the combined organics were dried over sodium sulfate, filtered and concentrated to give 558 mg (27%) of (5-fluoro-pyridin-2-yl)- methylamine as a yellow oil which was used without further purification.

The synthetic route of 327056-62-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52605-96-6, 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

To a solution of Compound 4 (100 mg) in 2-propanol (5 ml) were added 2-chloro-3-methoxy pyridine (182 mg) and concentrated sulfuric acid (165 mg). It was stirred under refluxing for 48 hours. The solvent was removed under reduced pressure. Saturated sodium bicarbonate solution and water were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. The obtained residue was purified by column chromatography. The obtained solid was recrystallized with diethylether-hexane to give Compound I-17 (76.8 mg).1H-NMR (CDCl3) delta: 1.70 (3H, s), 3.88 (3H, s), 4.65 (2H, br), 6.23-6.33 (2H, m), 6.66 (1H, dd, J=10.2, 5.2 Hz), 6.91-7.02 (3H, m), 7.43 (1H, dd, J=7.1, 2.9 Hz), 7.78 (1H, dd, J=5.0, 1.3 Hz), 7.84-7.91 (1H, m)

Statistics shows that 52605-96-6 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-methoxypyridine.

Reference:
Patent; SHIONOGI & CO., LTD.; US2012/238557; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 695-98-7, 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 695-98-7 as follows.

In dichloromethane (15.0 ml), 2,3,5-trimethyl-pyridine (1.29 g) was dissolved. The reaction solution was cooled to 0°C and added with meta-chloroperbenzoic acid (2.53 g), followed by stirring at room temperature for 1.5 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. Subsequently, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resulting residue in dichloromethane (25.0 ml). The reaction solution was added with trifluoroacetic anhydride (2.8 ml) and subjected to thermal reflux for 3.5 hours. After the reaction solution had been cooled to room temperature, the solvent was distilled off. The residue obtained was dissolved in methanol (60.0 ml). After having been cooled to 0°C, the reaction solution was added with a 12.5percent sodium methoxide/methanol solution to adjust to pH 10, followed by stirring at room temperature for 16.5 hours. After the solvent had been distilled off, the residue was added with distilled water and extracted with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and the solvent was then distilled off, followed by dissolving the resulting residue in chloroform (30.0 ml). The reaction solution was added with manganese dioxide (chemically processed product) (6.10 g) and then stirred at room temperature for 18 hours. The reaction solution was filtrated through Celite. The solvent in the filtrate was distilled off and the residue obtained was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.14 g) as a yellow oily substance. MS(FAB,Pos.):m/z=136[M+H]+1H-NMR(500MHz,CDCl3):delta=2.40(3H,s),2.63(3H,s),7.43(1H,brs),8.48(1 H,brs),10.16(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,695-98-7, its application will become more common.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63572-73-6 ,Some common heterocyclic compound, 63572-73-6, molecular formula is C6H4N4O2, 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.

To a solution of 5-nitro-1H-pyrazolo [4,3-b]pyridine (7.3 g,38.0 mmol) in MeOH (240 mL) was added 10% wt Pd/C (4.03,3.8 mmol). The reaction mixture was hydrogenated underhydrogen (1 atm) for 16 h. The Pd/C was removed by filtration, andthe filtrate was concentrated to give 1H-pyrazolo [4,3-b]pyridin-5-amine (5.1 g, 82% yield) as a light brown solid. Rf: 0.33 (DCM/MeOH,19/1, v/v). Mp: 178 C. 1H NMR (DMSO-d6, 400 MHz) d 13.12 (s, 1H),8.05 (d, J 2.4 Hz, 1H), 7.81 (s, 1H), 7.18 (d, J 2.3 Hz, 1H), 5.04 (s,2H). MS (ESI)m/z:134.8 [MH],156.7 [MNa], 301.0 [2MNa].

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. 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hao, Chenzhou; Huang, Wanxu; Li, Xiaodong; Guo, Jing; Chen, Meng; Yan, Zizheng; Wang, Kai; Jiang, Xiaolin; Song, Shuai; Wang, Jian; Zhao, Dongmei; Li, Feng; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 131; (2017); p. 1 – 13;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98121-41-6, 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 98121-41-6, name is 3-Amino-5,6-dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A 5L flask with mechanical stirrer, thermocouple, and addition funnel was charged with the product of Example 2C (70 g, 429 mmol) and 48% HBraq (240 mL). The suspension was maintained at 0-5 C. as a solution of NaNO2 (32.0g, 464 mmol) in water (100 mL) was added dropwise over 1 hour. Additional water (200 mL) was added and the mixture was stirred for 10 minutes at 0-5 C. The mixture was treated with CuBr (32.6 g, 227 mmol) in portions over 20 minutes followed by additional water to maintain a fluid reaction mixture. The mixture was allowed to warm to room temperature and diluted with water. The mixture was distilled at ambient pressure, until the distillate ran clear (1.5 L collected). The distillate was extracted with EtOAc (3*500 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), and concentrated to provide 5-bromo-2,3-dichloropyridine as a solid. 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, J=3 Hz, 1H), 8.38 (d, J=3 Hz, 1H).

According to the analysis of related databases, 98121-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242644; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6854-07-5, 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. 6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, molecular formula is C6H4N2O5, The 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.

b) 2-Chloro-5-nitro-nicotinic acid 2-Hydroxy-5-nitro-nicotinic acid (2.7 mmol) in a mixture of NJV- dimethylformamide (2.7 mmol) and thionyl chloride (5 ml) was heated at 80 0C for 1 h. The mixture was allowed to cool and concentrated in vacuo. To the resulting residue was added ice-water (20 ml) and with vigorous stirring a precipitate formed. The precipitate was filtered off and dried in a vacuum oven to give a white solid (68%).ESIMS: M-I: found 201 ; expected 201; and1H NMR (300 MHz, DMSO) ? 9.30 (IH, d, H-4), 8.83 (IH, d, H-6).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid.

Reference:
Patent; BIONOMICS LIMITED; WO2008/46135; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem