Category: pyridine-derivatives

Synthetic Route of 1151989-04-6, 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 1151989-04-6, name is 4-Nitrophenyl 4-(pyridin-2-yldisulfanyl)benzyl carbonate. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound 8.; A solution of the disulfide 4 (see Senter, P. D.; Pearce, W. E.; Greenfield, R. S. /. Org Chem. 1990, 55, 2975-2978) (7 mg, 28 mumol) in dry dichloromethane (2 mL) was added to a stirred solution of bis(4-nitrophenyl) carbonate (12.8 mg, 42 mumol) and 4-(dimethylamino) pyridine (10.3 mg, 84 mumol) in dry dichloromethane (2 mL). After being stirred at room temperature for 12 h, paclitaxel (47.8 mg, 56 mumol) was added. The reaction mixture was allowed to stir at room temperature for another 12 h (see Fardis, M.; Pyun, H.-J.; Tario, J.; Jin, H.; Kim, C. U.; Ruckman, J.; Lin, Y.; Green, L.; Hicke, B. Bioorg. Med. Chem. 2003, 11, 5051-5058; Liu, C; Schilling, J. K.; Ravindra, R.; Bane, S.; Kingston, D. G. I. Bioorg. Med. Chem. 2004, 12, 6147-6161.) Workup as described above and purification by preparative TLC (30% EtOAc/hexanes) afforded compound 8 (25.3 mg, 80%): 1H NMR (CDCl3). delta 8.48 (IH, d, / = 4.6 Hz), 8.13 (2H, d, J = 8.0 Hz), 7.71 (2H, d, / = 8.3 Hz), 7.25-7.65 (17H, m), 7.13 (IH, br dd, / = 5.1, 3.3 Hz), 6.88 (IH, d, J = 9.2 Hz), 6.29 (2H, br s), 5.97 (IH, br d, / = 9.2 Hz), 5.68 (IH, d, / = 7.0 Hz), 5.42 (IH, br s), 5.13 (IH, d, / = 12.3 Hz), 5.09 (IH, d, / = 12.3 Hz), 4.97 (IH, d, / = 9.4 Hz), 4.43 (IH, dd, J = 10.6, 6.9 Hz), 4.31 (IH, d, / = 8.5 Hz), 4.20 (IH, d, / = 8.5 Hz), 3.80 (IH, d, J = 7.0 Hz), 2.56 (IH, m), 2.44 (3H, s), 2.39 (IH, dd, J = 15.4, 9.4 Hz), 2.23 (3H, s), 2.19 (IH, dd, J = 15.4, 8.7 Hz), 1.91 (3H, s), 1.88 (IH, m), 1.68 (3H, s), 1.25 (3H, s), 1.13 (3H, s); 13C NMR (CDCl3) delta 203.8, 171.3, 169.8, 167.8, 167.1, 167.1, 159.2,154.0, 149.6, 142.6, 137.4, 136.6, 133.6, 133.4, 133.4, 132.8, 132.1, 130.2, 129.1, 129.1,129.1, 128.7, 128.7, 128.5, 127.4, 127.1, 126.5, 121.1, 119.8, 84.4, 81.1, 79.2, 77.2, 76.9, 76.4, 75.6, 75.1, 72.1, 72.1, 70.0, 58.5, 52.7, 45.6, 43.2, 35.6, 35.6, 26.8, 22.7, 22.2, 20.8, 14.8, 9.6; HRFABMS m/z 1129.3433 [M + H+] (calcd for C60H6IN2Oi6S2, 1129.3463).

According to the analysis of related databases, 1151989-04-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIRGINIA TECH INTELLECTUAL PROPERTIES, INC.; WO2009/62138; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

Example 7: Preparation of [N’- (3- { [5-bromo-2- (3-chloro- pyridin-2-yl) -2ff-pyrazole- 3-carbonyl] -amino} -6-chloro- 4- methyl-pyridine-2-carbonyl) -hydrazinecarboxylic acid methyl ester (7); Step 1: Preparation of 3-amino-6-chloro-2-iodo-4- methylpyridine 5-Amino-2-chloro-4-methylpyridine (1.35 g) was dissolved in DMF (20 mL) , N-iodosuccinimide (2.59 g) was added and the reaction mixture was stirred at room temperature for 12 hours. Ethyl acetate was added and the organic layer was washed 3x with water, washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate = 3:1, Rf = 0.30) to afford 1.38 g of the title compound of as an orange solid.1H-NMR (CDCl3, TMS) delta (ppm) : 2.21 (3H, s) , 4.06 (2H, br s), 6.95 (IH, s) .

Statistics shows that 66909-38-4 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1796-84-5, 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 1796-84-5 as follows.

Compound 3c (3.0 g, 13.2 mmol), 4-ethoxy-3-nitropyridine (2.7 g, 13.2 mmol) and DIPEA (1.89 g, 14.6 mmol) were dissolved in N-methylpyrrolidinone (5 ml). The reaction mixture was heated to 120 C. for 18 hours. The reaction solution was cooled, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated. Then ether was added to precipitate solids, and compound 3d (1.5 g, 33%) was obtained by suction filtration. MS: 347.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1796-84-5, its application will become more common.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; LIU, Hong; WU, Beili; ZHENG, Yongtang; XIE, Xin; JIANG, Hualiang; PENG, Panfeng; LUO, Ronghua; LI, Jing; LI, Jian; ZHU, Ya; CHEN, Ying; ZHANG, Haonan; YANG, Liumeng; ZHOU, Yu; CHEN, Kaixian; (94 pag.)US2017/44187; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84199-61-1, 3-Acetyl-2-bromopyridine, 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: C7H6BrNO, blongs to pyridine-derivatives compound. Formula: C7H6BrNO

Synthesis of 7-phenylquinolin-5-ol (6.1) for Example 1[0271] 3-Acetyl-2-bromopyridine, 56 muL phenylacetylene, 170 muL DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25 C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g SiO2, cyclohexane?cyclohexane/ethylacetate 70:30) to yield 40 mg 1-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E), M+H=222

The synthetic route of 84199-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-carboxamide, 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: C6H5BrN2O, blongs to pyridine-derivatives compound. Formula: C6H5BrN2O

Description 9: 5-bromopicolinonitril D9)Phosphorus oxychloride (1 1 1 g, 0.720 mol) was added to a mixture of 5- bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2S04, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1 . Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.1 HNMR (400 MHz, CHLOROFORM-d) delta (ppm): 7.60 (d, J = 8.4 Hz, 1 H), 8.00 (dd, J = 6.0, 2.0 Hz, 1 H), 8.79 (d, J = 2.0 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
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 183428-91-3, name is 2-Amino-3-methyl-5-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 183428-91-3

A solution of 6-amino-5-methyl-pyridine-3-carbonitrile (31 mg, 0.23 mmol) in sulfuric acid (0.37 mL) was stirred at rt for 3 days. The mixture was poured onto ice and then it was carefully basified with NH4OH. The mixture was extracted with EtOAc. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield intermediate compound 1-117 (50 mg, 100%) as a beige solid.

With the rapid development of chemical substances, we look forward to future research findings about 183428-91-3.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ALONSO-DE DIEGO, Sergio-Alvar; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; CONDE-CEIDE, Susana; ANDRES-GIL, Jose, Ignacio; DELGADO-GONZALEZ, Oscar; TRESADERN, Gary, John; TRABANCO-SUAREZ, Andres, Avelino; (211 pag.)WO2016/16395; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1227048-78-3, Methyl 2-amino-5-iodonicotinate, 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, 1227048-78-3, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 2-amino-5-iodonicotinate

Preparation 76: 2-Amino-5-(4-fluorophenoxy)nicotinic add methyl ester To 2-aminonicotimc acid methyl eater (5.5g, 36.2mmol) in DMF (70mL) was added N-iodosuccinimide (9.8g, 43.7rmnol). After 16h the mixture was poured into sat. sodium thiosulfite solution and then extracted with Et20. The organic phase was washed with water, brine, dried (MgS04) and the solvent was removed in vacuo to give 2-amino-5-iodonicotinic acid methyl ester. To 4-fluorophenol (2.4g, 21.6mmol) in dioxane (50mL) was addedCS2CO3 (6g, 25.2mmol) and the mixture was heated to 50C. After 20min Cul (0.56g, 3.0mmol) and 2-ammo-5-iodonicotrriic acid methyl ester (2g, 7.2mmol) were added and the mixture heated under reflux for 16h. After cooling the solvent removed in vacuo, the residue was partitioned between EtOAc and 4N HQ, the organic phase was extracted with 6N HC1 and the organic phase discarded. The combined aqueous phase was basified with NH4OH and re-extracted with EtOAc. The organic phase was dried (MgS04) and the solvent was removed in vacuo. The residue was purified by column chromatography (1 :3EtOAcrHexane) to give, after removal of the solvent in vacuo, the title compound: RT= 3.30min; m/z (ES+) = 263.2 [M+ Iff”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227048-78-3, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; BLOXHAM, Jason; BRADLEY, Stuart Edward; SAMBROOK-SMITH, Colin Peter; SMYTH, Donald; KEILY, John; DAWSON, Graham John; RASAMISON, Chrystelle Marie; BELL, James Charles; WO2011/117254; (2011); A1;,
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 145255-19-2, name is 5-Aminopyridine-2-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-Aminopyridine-2-carboxamide

2-Chloro-3-fluoro-6-[2-methoxy-4-(trifluoromethoxy)phenoxy]benzoyl chloride was dissolved in THF (2 mL) and cooled to 0 C. DIEA (138 mu, 0.792 mmol) and 5-aminopyridine-2- carboxamide (40 mg, 0.29 mmol) were added and the resulting suspension was stirred at 0 C for 30 minutes and then allowed to warmed to room temperature and stirred for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic later was separated, dried by passing through a phase separation cartridge and concentrated in vacuo. Silica gel chromatography (0- 100% ethyl acetate/petroleum ether) provided 5-[[2-chloro-3-fluoro-6-[2-methoxy-4- (trifluoromethoxy)phenoxy]benzoyl]amino]pyridine-2-carboxamide (85 mg, 64%). ESI-MS m/z calc. 499.06, found 500.0 (M+l)+;497.9 (M-l)-; retention time (Method E): 3.01 minutes (5 minute run). NMR (400 MHz, DMSO-d6) delta 11.25 (s, 1H), 8.86 (d, J = 2.4 Hz, 1H), 8.28 (dd, J = 8.6, 2.5 Hz, 1H), 8.09 – 7.99 (m, 2H), 7.56 (s, 1H), 7.49 (t, J = 9.0 Hz, 1H), 7.23 – 7.16 (m, 2H), 6.98 (ddd, J = 8.9, 2.8, 1.3 Hz, 1H), 6.84 (dd, J = 9.3, 3.9 Hz, 1H), 3.77 (s, 3H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 145255-19-2.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); 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. 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, the common compound, a new synthetic route is introduced below. Product Details of 1111637-74-1

Step 2: 5-bromo-3-methyl-lH-pyrazolo[3,4-b]pyridine To a solution of l-(5-bromo-2-fluoropyridin-3-yl)ethanone (43 g, 197.2 mmol) in ethanol (500 niL) was added hydrazine monohydrate (34.8 g, 591.6 mmol, 85 %) at RT. After addition, the reaction mixture was refluxed overnight. The reaction mixture was cooled to RT and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 5% to 17% ethyl acetate in petroleum ether) affording 5-bromo-3-methyl-lH-pyrazolo[3,4-b]pyridine (35g, 83.7%): NMR (400 MHz, DMSO-d6): delta 13.42 (s, 1H), 8.51 (m, 2H), 2.54 (s, 3H).

The synthetic route of 1111637-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1111637-94-5 ,Some common heterocyclic compound, 1111637-94-5, molecular formula is C8H7BrN2, 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-bromo-3-methyl-1H-pyrrolo [2, 3-b] pyridine (1.50 g, 7.11 mmol) in 5 mL of DCM were added DMAP (0.080 g, 0.71 mmol) and di-tert-butyl dicarbonate (1.55 g, 7.11 mmol) . The resulting solution was stirred for 1 h at room temperature and then concentrated under reduced pressure to afford tert-butyl 5-bromo-3-methyl-1H-pyrrolo [2, 3-b] pyridine-1-carboxylate as a white solid which was used in the subsequent step without further purification. MS (EI) calc?d for C13H16BrN2O2[M+H]+, 311 found, 311.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-94-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem