Pyridine-derivatives

Synthetic Route of 75903-58-1, 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. 75903-58-1, name is 6-Aminopyridine-2-sulfonamide, molecular formula is C5H7N3O2S, 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.

Example 225 (2S,3R,4S,5S)-N-(6-aminopyridine-2-sulfonyl)-3-tert-butyl-4-[(5-cyclobutyl-2-methoxypyridin-3-yl)methoxy]-5-(2-cyclopropylphenyl)-1-[(2S)-oxane-2-carbonyl]pyrrolidine-2-carboxamide (2S,3R,4S,5S)-3-(tert-Butyl)-4-((5-cyclobutyl-2-methoxypyridin-3-yl)methoxy)-5-(2-cyclopropylphenyl)-1-((S)-tetrahydro-2H-pyran-2-carbonyl)pyrrolidine-2-carboxylic acid (Example 171B) (48.8 mg, 0.083 mmol) and di(1H-imidazol-1-yl)methanone (20.09 mg, 0.124 mmol) were combined in N,N-dimethylformamide (1 mL) and warmed to 65 C. for 1 hour. 6-Aminopyridine-2-sulfonamide (14.31 mg, 0.083 mmol) was dissolved in 0.3 mL of N,N-dimethylformamide and sodium hydride (3.47 mg, 0.087 mmol) (60% dispersion in mineral oil) was added in portions. The reaction was stirred at ambient temperature for one hour, the mixture was added to the NaH/sulfonamide suspension and the resulting mixture was stirred at ambient temperature for 16 hours. The solvent was reduced in volume and the crude material was quenched with water and 1N aqueous HCl was added dropwise to acidic pH. The resulting precipitate was filtered and washed with water. The crude precipitate was purified by reverse-phase preparative HPLC on a Phenomenex Luna C8(2) 5 mum 100 A AXIA column (30 mm*150 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 10% A, 0.5-7.0 minutes linear gradient 10-95% A, 7.0-10.0 minutes 95% A, 10.0-12.0 minutes linear gradient 95-10% A) to provide the title compound as the trifluoroacetic acid salt. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.74 (d, J=2.5 Hz, 1H), 7.63 (dd, J=7.5, 1.7 Hz, 1H), 7.44 (dd, J=8.3, 7.3 Hz, 1H), 7.13 (dd, J=7.3, 0.9 Hz, 1H), 7.11-7.04 (m, 2H), 6.94 (dd, J=7.5, 1.6 Hz, 1H), 6.78 (d, J=2.4 Hz, 1H), 6.64 (dd, J=8.4, 0.8 Hz, 1H), 5.89 (d, J=6.1 Hz, 1H), 4.57 (d, J=2.6 Hz, 1H), 4.31 (dd, J=6.1, 1.7 Hz, 1H), 4.23 (d, J=13.4 Hz, 1H), 3.95 (d, J=9.0 Hz, 1H), 3.91 (s, 1H), 3.77 (s, 1H), 3.74 (s, 3H), 3.69-3.56 (m, 1H), 3.33-3.27 (m, 3H), 2.55 (t, J=2.2 Hz, 1H), 2.27-2.13 (m, 2H), 2.04-1.79 (m, 4H), 1.71-1.62 (m, 1H), 1.54-1.43 (m, 1H), 1.36 (dt, J=8.8, 4.3 Hz, 2H), 1.22-1.07 (m, 1H), 1.00 (s, 9H), 0.96-0.82 (m, 2H), 0.71 (ddd, J=9.1, 5.5, 3.8 Hz, 1H), 0.46 (ddd, J=9.5, 6.4, 3.7 Hz, 1H); MS (APCI+) m/z 746 (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 75903-58-1, 6-Aminopyridine-2-sulfonamide.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (247 pag.)US2018/99932; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6271-78-9, 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 6271-78-9, name is 6-Chloropyridine-3-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

Example 754 6-(3-{[2-amino-6-(3-chloro-2-methylphenyl)pyrimidin-4-yl]amino}propoxy)pyridine- 3-carboxamide. A mixture of 3-{[2-amino-6-(3-chloro-2-methylphenyl)pyrimidin-4-yl]amino}propan- 1 -ol (intermediate 60), 6-chloropyridine-3-carboxamide (1.1 equiv.) and Cs2C03 (2.0 equiv.) in DMSO was heated in a sealed tube at 90C for 2 h. After cooling was methanol added to the solution, followed by filtration and purification by preparative LC to furnish the title compound. LCMS [M+H]+ 413. 1 H NMR (400 MHz, METHANOL-^) delta ppm 8.67 (dd, J=2.5, 0.6 Hz, 1 H), 8.13 (dd, J=8.8, 2.5 Hz, 1 H), 7.58 – 7.63 (m, 1 H), 7.29 – 7.40 (m, 2 H), 6.86 (dd, J=8.8, 0.6 Hz, 1 H), 6.03 (s, 1 H), 4.48 (t, J=6.2 Hz, 2 H), 3.72 (t, J=6.6 Hz, 2 H), 2.37 (s, 3 H), 2.15 (quin, J=6.4 Hz, 2 H).

According to the analysis of related databases, 6271-78-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 66909-29-3, 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.66909-29-3, name is 6-Chloro-5-methylnicotinic acid, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.

c) A solution of 6-chloro-5-methyl-nicotinic acid (13.85 g, 80.75 mmol) in dry EtOH (200 mL) containing some drops of concentrated H2SO4 is stirred at reflux for 2 days. The solution is cooled to rt, the solvent evaporated, the residue dissolved in EA (200 mL) and washed with a solution of sat. aq. Na2CO3 (2¡Á80 mL), 1M aq. KHSO4 (2¡Á80 mL) and brine (50 mL). The org. phase is dried over MgSO4, filtered and evaporated to give 6-chloro-5-methyl-nicotinic acid ethyl ester (12.65 g) as a solid; LC-MS: tR=0.92 min; [M+1]+=200.10; 1H NMR (300 MHz, CDCl3) delta 1.43 (t, J=7.0 Hz, 3H), 2.46 (s, 3H), 4.43 (q, J=7.3 Hz, 2H), 8.16 (m, 1H), 8.84 (d, J=2.0 Hz, 1H).

Statistics shows that 66909-29-3 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-5-methylnicotinic acid.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; US2010/168005; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1008304-85-5, 2-Chloro-6-methoxypyridin-4-amine, 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, 1008304-85-5, blongs to pyridine-derivatives compound. Computed Properties of C6H7ClN2O

To a solution of 2-chloro-6-methoxypyridin-4-amine (790 mg, 5.00 mmol) in CH3CN (5 mL)was added water (5 mL) and conc. HCI (5 mL). Then a solution of NaNO2 (690 mg, 10.0mmol) in water (5 mL) was added dropwise at 0 C. After stirred at 0 C for 10 mm a solution of KI (1.66 g, 10.0 mmol) in water (5 mL) was added dropwise at 0C. The mixture was stirred at 0 C for 20 mm. Then, the reaction was quenched with sat. Na2S2O3 solution (50 mL). EtOAc (20 mL x 3) was added to extract desired compound. The combined organiclayers were washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (PE)to give the title compound (1.1 g, yield 82%) as white solid.D490 1H NMR (300 MHz, CDCI3): O 7.26 (s, 1H), 7.07 (s, 1H), 3.91 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1008304-85-5, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; DING, Xiao; JIN, Yun; LIU, Qian; REN, Feng; SANG, Yingxia; STASI, Luigi Piero; WAN, Zehong; WANG, Hailong; XING, Weiqiang; ZHAN, Yang; ZHAO, Baowei; (573 pag.)WO2017/12576; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 769-28-8, 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. 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, molecular formula is C8H8N2O, 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.

1-methyl-4-cyano-5,6,7,8-tetrahydroisoquinolone (14.8 g, 0.1 mol) was added to a solution of methanol and added5g of self-manufactured Raney Nickel and 15ml of ammonia, replace it with nitrogen and replace it with hydrogen. Maintain the hydrogen pressure under confined conditionsAt 10 MPa, slowly warm up to 72C and stir overnight. Stop the reaction. After TLC monitoring reaction is complete, cool to room temperature and filter to removeAgents. The reaction solution was concentrated in vacuo to give a colorless oil that solidified upon standing.

According to the analysis of related databases, 769-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University; Puluo Pharmaceutical Co., Ltd.; Yu Luoting; Wei Yuquan; (24 pag.)CN107573327; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 17282-00-7, name is 3-Bromo-5-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 3-Bromo-5-methylpyridin-2-amine

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

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, 17282-00-7, 3-Bromo-5-methylpyridin-2-amine.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, molecular formula is C8H12N2O, molecular weight is 152.1937, as common compound, the synthetic route is as follows.Product Details of 771579-27-2

[0793] Step 4: Synthesis of 3-bromo-N-((4,6-dimethyl-2-oxo-l ,2-dihydropyridin-3- yl)methyl)-l-isopropyl-6-(4-(morpholinomethyl)phenyl)-lH-pyrazolo[3,4-b]pyridine-4- carboxamide[0794] A solution of 3-bromo-l-isopropyl-6-(4-(morpholinomethyl)phenyl)-lH- pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.8 g, 1.74 mmol) and 3-(aminomethyl)-4,6- dimethylpyridin-2(lH)-one (0.53 lg, 3.49 mmol) in DMSO (8 raL) and was stirred at room temperature for 15 min. Then PYBOP (1.36 g, 2.62 mmol) was added to it and stirring was continued for 12 hr. After completion of the reaction, reaction mass was poured into ice to obtain solid, which was filtered and solid was purified by silica gel column cliromatography to obtain the desired compound (39% yield). LCMS: 593.20 (M + 1)+; HPLC: 97.49% (@ 254 nm) (R,;5.338); NMR (DMSO-i?, 400 MHz) delta 1 1.48 (bs, 1H), 8.67 (t, 1H, J=4.8 Hz), 8.18 (d, 2H, J= 8.4 Hz), 7.73 (s, 1H), 7.47 (d, 2H, .1=8.4 Hz), 5.87 (s, 1H), 5.33-5.30 (m, 1 H), 4.40 (d, 2H, J= 4.4 Hz), 3.58 (bs, 4H), 3.53 (s, 2H), 2.38 (bs, 4H), 2.26 (s, 3H), 2.1 1 (s, 3H), 1.52 (d, 6H, J=6.4 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,771579-27-2, 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William; WO2012/118812; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 4548-45-2, 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.4548-45-2, name is 2-Chloro-5-nitropyridine, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.

Intermediate B-54-(5-Aminopyridin-2-yl)-N-(2-fluorophenyl)piperazine- 1 -carboxamide (B-5) Step 1 : t-Butyl 4-(5-nitropyridin-2-yl)piperazine-l-carboxylate (B-2)To 5-nitro-2-chloropyridine (10.0 g, 0.0631 raol) and N-BOC-piperazine (17.6 g, 0.0946 mol) dissolved in DMF (200 mL) was added N,N-diisopropylethylamine (24.5 g, 31.3 mL, 0.189 mol). The reaction mixture was heated at 100 C for 16 h then cooled to RT and concentrated. Water (300 mL) was added, and the aqueous solution was extracted with CH2G2. The combined organic extract was dried (MgS0 ), filtered, and concentrated.Purification by vacuum filtration through silica gel (eluant: 5% EtOAc-CFkCL.) gave t-butyl 4-(5-nitropyridin-2-yl)piperazine-l-carboxylate (B-2) as a yellow solid (19.45 g, 100% yield). MS (M+l): 309.

The chemical industry reduces the impact on the environment during synthesis 4548-45-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 878805-23-3, 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 878805-23-3 as follows.

Example 77 N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide A solution of (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 80 mg, 0.31 mmol), 3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxylic acid (CAS number 1252907-86-0; 70 mg, 0.37 mmol), EDC (177 mg, 0.92 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (126 mg, 0.922 mmol) and DIPEA (161 mul, 0.92 mmol) in dry DCM (1 ml) was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate (20 ml) and water (10 ml). The organics were washed with water (2*10 ml), brine (10 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica, 0 to 100% ethyl acetate/petrol) followed by a trituration in pentane diethyl ether to afford the title compound. 1H NMR (400 MHz, DCM-d2) delta ppm 1.43 (s, 3H), 1.66-1.99 (m, 4H), 2.14-2.30 (m, 1H), 2.49-2.68 (m, 1H), 4.40-4.55 (m, 1H), 7.38-7.48 (m, 1H), 7.56 (br. s., 1H), 7.62-7.67 (m, 1H), 7.69 (br. s., 1H), 7.84 (s, 2H), 8.08-8.14 (m, 1H), 8.23 (br. s., 1H), 8.65-8.70 (m, 1H) MS ES+: 433 Example 89 3-Cyclopropyl-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide Prepared according to the procedure for N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 77) from (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 48 mg, 0.15 mmol), 3-cyclopropylpyridine-2-carboxylic acid (Intermediate 16; 33 mg, 0.20 mmol) and triethylamine (0.077 ml, 0.55 mmol) except this was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) followed by column chromatography (silica, 0-2.5% methanol/DCM) to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.58-0.80 (m, 2H), 1.05-1.17 (m, 2H), 1.39 (s, 3H), 1.61-2.08 (m, 4H), 2.12-2.24 (m, 1H), 2.63 (s, 1H), 3.28-3.43 (m, 1H), 4.46-4.59 (m, 1H), 7.31-7.37 (m, 2H), 7.78-7.89 (m, 2H), 8.23-8.33 (m, 2H), 8.33-8.38 (m, 1H) MS ES1: 406

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,878805-23-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19621-92-2, 6-Oxo-1,6-dihydropyridine-2-carboxylic acid, 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, Safety of 6-Oxo-1,6-dihydropyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Safety of 6-Oxo-1,6-dihydropyridine-2-carboxylic acid

At 25 C and N 2 atmosphere,To 6-hydroxypyridine-2-carboxylic acid (12 mmol)And pyridine (20 mmol)Add 20 mL of anhydrous dichloromethane solution1,3-Dicyclohexylcarbodiimide DCC (15 mmol).5 minutes later,Add 2-((1-Amino-2-methylpropan-2-yl)amino)-1-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)ethanone (10 mmol ),The mixture was stirred overnight.TLC (95:5 in dichloromethane:Methanol containing 2% ammonia)Indicates that all raw materials are consumed.The reaction was quenched with sodium bicarbonate and filtered through a pad of Celite.The stopper was rinsed with methylene chloride.The aqueous layer was extracted with dichloromethane.After the combined organic layers are dried over Na 2 SO 4 ,Filter and concentrate in vacuo,This gave 3.5 g of a light brown solid.The crude product was purified by flash chromatography.Use 2% to 8% MeOH:Purification by stepwise gradient of dichloromethane and 2% ammonia,Obtained 3.2 g of white powder as N-(2-((2-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-2-ethoxy)amino)-2-methylpropane ()-(6-hydroxypyridin-2-yl)-carboxamide,The yield was 94%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19621-92-2, 6-Oxo-1,6-dihydropyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Sang Qi; (10 pag.)CN108218865; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem