Category: pyridine-derivatives

Application of 19437-26-4 ,Some common heterocyclic compound, 19437-26-4, molecular formula is C11H8N2O, 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 300 mL three-necked flask was added 30 mL of a dehydrated THF solution of 4.12 g of Compound I and the mixture was stirred at -78 C.To this was dropped 6.3 mL of 1.58 M n-BuLi hexane solution, and the mixture was stirred for 2.5 hours. To this was added 45 mL of a dehydrated THF solution of 1.64 g of di-2-pyridinyl-methanone, and the mixture was stirred for 2 hours and then stirred at room temperature for 3 hours. After the reaction, 1N hydrochloric acid aqueous solution was added to this mixture and stirred for 1 hour. After washing with water and concentrating the obtained organic phase, a viscous solid was obtained. This viscous solid, 30 mL of glacial acetic acid and 1.4 mL of hydrochloric acid were placed in a 300 mL flask, and the mixture was heated and stirred at 130 C. for 2 hours under a nitrogen atmosphere to react. After the reaction, the reaction mixture was added dropwise to ice-cooled 150 mL of water. After precipitating white crystals, the produced solid was filtered off, washed with methanol and then dried. Finally, 4.15g (83% yield) of a white powder of Compound 111 was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19437-26-4, its application will become more common.

Reference:
Patent; SAMSUNG DISPLAY COMPANY LIMITED; ITOI, HIROAKI; MIYAKE, HIDEO; KAWAMURA, HISAYUKI; (119 pag.)JP2017/203026; (2017); A;,
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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 5345-47-1, name is 2-Aminonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H6N2O2

Equipped with a blender,Reflux condenser 500mL three-necked flask,20.7 g (0.15 mol) of 2-aminonicotinic acid,80 mL acetic acid,Stirred at room temperature,A constant pressure dropping funnel was added dropwise with a mixed solution of 40 mL of acetic acid and 4.1 mL of bromine (0.08 mol)Drop end to continue mixing 4-5h.filter,Washed with acetic acid,dry,The solid was refluxed with methanol 100mL 10min 10min at room temperature,Filter and dry.31.2g of white solid was obtained,Yield 96%.

With the rapid development of chemical substances, we look forward to future research findings about 5345-47-1.

Reference:
Patent; Southern Medical University; Wan Shanhe; Wang Guangfa; Wu Xiaoyun; Tian Yuanxin; Ye Ling; Li Zhonghuang; Zhang Tingting; Zhu Zhengguang; Jin Hong; Zhang Jiajie; (27 pag.)CN106565684; (2017); A;,
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Synthetic Route of 15069-92-8, Adding some certain compound to certain chemical reactions, such as: 15069-92-8, name is 5-Hydroxypicolinic acid,molecular formula is C6H5NO3, 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 15069-92-8.

A mixture of 5-hydroxypicolinic acid (10.0 g, 71.9 mmol), silver carbonate (79 g, 288.0 mmol), and methyl iodide (18.0 ml, 288.0 mmol) in acetonitrile (350 ml) was stirred at rt for 24 hours. Solids were removed through vacuum filtration and washed with ethyl acetate (3 x 80 ml). Filtrate was reconcentrated in vacuo, and the residue was purified by flash chromatography on silica gel using ethyl acetate and hexanes to afford the title compound as a light brown solid (7.2 g, 60% yield). ?H NMR is consistent with ?H NMR of commercially available 5-methoxypyridine-2-carboxylic acid methyl ester.

According to the analysis of related databases, 15069-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koay, Natalie; Tonelli, Devin L.; Truong, Vouy Linh; Tetrahedron Letters; vol. 52; 1; (2011); p. 122 – 124;,
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Pyridine | C5H5N – PubChem

Related Products of 573675-27-1, 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.573675-27-1, name is 3-Amino-5-bromopicolinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.

To a solution of 3-amino-5-bromopicolinonitrile (300 mg, 1.51 mmol) in 1,2-dichloroethane (5 mL) was added w-CPBA (1.23 g, 6.06 mmol) at 0 C. The reaction mixture was stirred 0 C for 1 h and then 80 C for 20 h. The reaction quenched with saturated aqueous Na2S203 (10 mL) and then extracted with DCM (10 mL x 3). The combined organics were dried over anhydrous Na2S04 and concentrated. The residue was purified by silica gel chromatography (20%-80% EtOAc /petroleum ether) to give the title compound. MS: 214, 216 (M+l).

Statistics shows that 573675-27-1 is playing an increasingly important role. we look forward to future research findings about 3-Amino-5-bromopicolinonitrile.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
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Electric Literature of 2002-04-2, 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.2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, molecular formula is C7H6N4S, molecular weight is 178.21, as common compound, the synthetic route is as follows.

Oxalyl chloride (0.1 rriL, 1.18 mmol, 4.0 eq.) was added to a solution of 4-(benzyloxy)-3- (2-methoxyethoxy)benzoic acid (0.1 g, 0.33 mmol, 1.15 eq.) in dichloromethane (2 rriL) followed by N,N-dimethylformamide (2 drops). The reaction was stirred at room temperature ovemight and the solvent was removed in vacuo. A suspension of 5- (pyrimidin-4-yl)-l,3,4-thiadiazol-2-amine (0.051 g, 0.29 mmol, 1 eq.) in pyridine (1.5 mL) was added and the reaction stirred at ambient temperature overnight. The resultant solid was collected by filtration and washed successively with pyridine (0.5 mL), water, saturated sodium bicarbonate solution and water and then dried in vacuo to afford 4- phenoxy-N-(5-(pyridin-4-yl)-l ,3,4-thiadiazol-2-yl)benzamide as a white solid (0.026 g, 13% yield). NMR (400 MHz, DMSO) 13.19 (1H, s), 8.75 (2H, d, J=6.1 Hz), 7.97 – 7.94 (2H, m), 7.85 (1H, d, J=2.1 Hz), 7.80 (1H, dd, J=2.1 , 8.5 Hz), 7.48 (2H, d, J=7.0 Hz), 7.41 (2H, dd, J=7.3, 7.3 Hz), 7.37 – 7.33 (1H, m), 7.24 (1H, d, J=8.7 Hz), 5.25 (2H, s), 4.27 – 4.23 (2H, m), 3.75 – 3.71 (2H, m), 3.34 (3H, s); MS (ESI+) 463.

The chemical industry reduces the impact on the environment during synthesis 2002-04-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
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Application of 1214336-90-9, 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 1214336-90-9 as follows.

2- Bromo-3-nitro-5-trifluoromethyl-pyridine (10.00 g, 36.87 mmol) was dissolved in toluene (250 ml) with stirring to give a pale yellow solution. Tetrabutylammonium bromide (11.90 g, 36.9 mmol) was added followed by copper(l) cyanide (9.92 g, 1 1 1 mmol) and the mixture was heated at reflux for 9 hrs. After cooling to RT, the reaction mixture was partitioned between water (750 ml) and EtOAc (750ml). The organic fractions were combined, washed with water (2 x 250 ml) and brine (100 ml), dried (MgS04) and concentrated in vacuo to afford the title product. H-NMR: [400MHz, DMSO-d6] ? 9.55 (1 H, m, ArH), 9.24 (1 H, m, ArH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1214336-90-9, its application will become more common.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUTLER, Rebecca; COLLINGWOOD, Stephen, Paul; HALL, Edward, Charles; EDWARDS, Lee; LEGRAND, Darren, Mark; SPIEGEL, Katrin; WO2013/38386; (2013); A1;,
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Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1072-97-5, 5-Bromopyridin-2-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, Product Details of 1072-97-5, blongs to pyridine-derivatives compound. Product Details of 1072-97-5

Another literature procedure to perform aromatic substitutions with the methoxy anion was followed.12 The method uses salts of copper (I) and a small amount of ester to form a stabilized tetrahedral adduct which should act as a powerful methoxide donor (Figure 3). Unfortunately, due to the presence of the free amino group on the bromopyridine and the ethyl acetate as co-catalyst, the reaction product was just the acetamide of the substrate (eq 2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1072-97-5, 5-Bromopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; THE GOVERNMENT OF THE UNITED STATES, as represented by the secretary of HEALTH AND HUMAN SERVICES; WO2007/124345; (2007); A2;,
Pyridine – Wikipedia,
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Electric Literature of 609-71-2, 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.609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C6H5NO3, molecular weight is 139.1088, as common compound, the synthetic route is as follows.

2-Hydroxynicotinic acid (4 g, 17.97 mmol) was suspended indichloromethane (115 mL) and DMF (1.15 mL) and then oxalylchloride (2M in CH2Cl2 solution, 3 eq, 43 mL) was added slowlyunder Ar flow (gas evolved). The mixture was stirred at rt tillcompletion of reaction by LC-MS, 4 h. The reaction mixture wasconcentrated under vacuum and further dried in vacuum pump.The crude product, 2-chloronicotinoyl chloride, was used in nextstep assuming quantitative yield. A suspension of 2-chloronicotinoyl chloride (3.16 g, 17.95 mmol) in THF (72 mL) wasadded to a mixture of 2-amino-5-nitrophenol (1.15 eq, 3.18 g) andDIPEA (1.7 eq, 5.3 mL) in THF (72 mL) at 0 C. The reaction mixturewas stirred at 0 C for 2 h and then allowed to get rt. The solids insuspension were filtered out and washed with ethyl acetate. Thefiltrate was washed with water and brine. The organic layer wasdried (Na2SO4) and concentrated to render a solid that was trituratedwith CH2Cl2 affording 3 (brownish solid, 3.76 g, 70%); 1H NMR(700 MHz, DMSO) d 8.68 (dd, J 4.7, 2.0 Hz, 1H), 8.64 (m, 1H), 8.10(d, J 2.5 Hz, 1H), 7.97 (dd, J 9.1, 2.5 Hz, 1H), 7.67 (m, 1H), 6.85 (m,3H). LCMS (ESI): m/z 212 [M H]; Rt: 4.05 min.

Statistics shows that 609-71-2 is playing an increasingly important role. we look forward to future research findings about 2-Oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Article; Albarran, M. Isabel; Amezquita-Alves, Adrian; Blanco-Aparicio, Carmen; Cebria, Antonio; Garcia, Ana Belen; Garcia-Campos, Francisco Javier; Martinez-Gago, Jaime; Martinez-Gonzalez, Sonia; Martinez-Torrecuadrada, Jorge; Munoz, Ines; Pastor, Joaquin; European Journal of Medicinal Chemistry; vol. 201; (2020);,
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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;,
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Related Products of 5654-97-7 , The common heterocyclic compound, 5654-97-7, name is 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one, molecular formula is C7H6N2O, 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.

EXAMPLE 3 4-{[(2-oxo-1,2-Dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)methyl]amino}benzenesulfonamide Dimethylformamide di-tert-butyl acetal (180 mg, 0.89 mmol) was added to a solution of 1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one (70 mg, 0.52 mmol) in 0.25 ml DMF, and the reaction mixture was slowly warmed to 100 C. The cooled solution was then diluted with 5 ml of ethanol. Sulfanilamide (172 mg, 1.00 mmol) and methanesulfonic acid (60 mg, 0.63 mmol) were added, and the reaction mixture was stirred at reflux for 2 h. The cooled solution was diluted with 4 ml of water, treated with NaHCO3 (70 mg, 0.83 mmol) and stirred 10 min. The resulting solid was filtered, washed with water and ethanol, and then suspended in boiling methanol and filtered upon cooling. Inorganics were removed by filtration through a short silica gel column, eluding with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): delta (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz, 1H), 7.77 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.6 Hz, 2H), 7.25 (s, 2H), 6.93 (dd, J=7.3, 5.1 Hz, 1H); (E) 10.79 (s, 1H), 9.70 (d, J=13.4 Hz, 1H), 8.23 (d, J=7.3 Hz, 1H). ESI-MS m/z 315 (M-H). Anal. Calcd. for C14H12N4O3S. 0.5 H2O: C, 51.68; H, 4.03; N, 17.03. Found: C, 51.75; H, 3.95; N, 17.26.

The synthetic route of 5654-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6624171; (2003); B1;,
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