Category: pyridine-derivatives

Application of 1443759-42-9, 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 1443759-42-9 as follows.

36.3: 4-Bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester To a mixture of 3.47 mL (29.3 mmol) tert-butyl nitrite and 6.60 g (29.3 mmol) copper(II)bromide in 120 mL acetonitrile was added a solution of 3.33 g (18.3 mmol) 4-amino- 6-methoxy-pyridine-2-carboxylic acid methyl ester in 30 mL acetonitrile dropwise at 40 C. This mixture was stirred at 80 C for 1 h, then poured into ice water. The precipitate was filtered off, washed with water and dried. The crude material was purified by flash chromatography (PE/EtOAc = 4/1 -> 3/1). yield: 2.50 g (56 %) + ESI-MS: m/z = 246 (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,1443759-42-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 145255-19-2, 5-Aminopyridine-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, Application In Synthesis of 5-Aminopyridine-2-carboxamide, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Aminopyridine-2-carboxamide

EXAMPLE 238: 4-[4-(6-CarbamoyIpyridin-3-ylamino)-7No.-pyrrolo[2,3-rf]pyriraidin-6-yl]-3,6-dihydro-2JHr-pyridme-l-carboxylic acid tert-butyl ester; .NH2^»[673] Into the DMF (ImL) solution of 4-(4-chloro-7No.-pyrrolo[2,3-J]pyrimidin-6-yl)-3,6-dihydro-2/ir-pyridine-l-carboxylic acid tert-butyl ester (122mg, 0.363mmol) wasadded t-BuOK (1M in ^-BuOH, 0.726mL, 0.726mmol) dropwise at RT under N2 over 5min.The mixture was then put in an ice/water bath and stirred for lOmin. After that time, theDMF (ImL) solution of 5-aminopyridine-2-carboxylic acid amide (99.5mg, 0.726mmol) wasadded into the above mixture dropwise. The reaction mixture was warmed to RT.Pd2(dba)3-CHCl3 (9.4mg, 2.5%eq.) and^(+)-BINAP (22.6mg, O.leq.) were added, and themixture was heated at 100C for 24h. The mixture was filtered and the filtrate wasconcentrated in vacua. The crude was submitted to MS directed purification. A brown oilwas obtained that was purified further by HPLC to obtain the title compound as an off-whitesolid. ‘H NMR (DMSO-dft 400 MHz): 5 = 1.50 (s, 9 H), 2.50 (m, 2 H), 3.64 (t, 2 H, J= 5.6Hz), 4.12 (bra, 2 H), 6.50 (bra, 1 H), 6.88 (s, 1 H), 7.53 (d, 1 H, J= 4.2 Hz), 8.04 – 8.05 (m, 1H), 8.08 (d, 1 H, J= 8.8 Hz), 8.44 (s, 1 H), 8.68 (dd, 1 H, /= 2.4 & 8.4 Hz), 9.12 (d, 1 H, J=2.4 Hz), 9.91 (s, 1 H), 12.18 (s, 1 H). MS (ES+): m/z 436.10 (100) [MET]. HPLC: fe = 2.75min (ZQ2000, polar_5 min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145255-19-2, 5-Aminopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885168-04-7, 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.885168-04-7, name is 5-Bromo-3-chloropicolinaldehyde, molecular formula is C6H3BrClNO, molecular weight is 220.4511, as common compound, the synthetic route is as follows.

To a solution of Compound 1 (10 g) in methylene chloride (200 mL) were added oxalyl chloride (4.43 mL) andN,N-dimethylformamide (0.16 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours.The reaction solution was concentrated under reduced pressure, the residue was dissolved in tetrahydrofuran (50 mL),and this was added dropwise to a suspension of thiosemicarbazide (3.85 g) and pyridine (75 mL) under ice cooling over10 minutes. After dropwise addition, the mixture was stirred at room temperature for 2 hours and concentrated underreduced pressure. The residue was dissolved in a 2N aqueous sodium hydroxide solution (210 mL), and heated at refluxfor 16 hours. The reaction solution was ice cooled and neutralized with concentrated hydrochloric acid (35 mL). Thedeposit was collected by filtration and washed with water and methanol. The obtained solid was suspended and washedin diethyl ether (50 mL), collected by filtration and dried at 50 C under reduced pressure to obtain Compound 2 (9.46g) as a beige solid.MS (m/z): 291/293/295 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 885168-04-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; SARUTA, Kunio; HAYASHI, Norimitsu; SAKURAI, Osamu; SAWAMOTO, Hiroaki; OBOKI, Eri; EP2862856; (2015); A1;,
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. 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate

A clean, nitrogen purged reactor was charged with methylene chloride (471 L) and 2,3,3a,4,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester (prepared according to Preparation Five, Step E, 47.0 kg, 1.0 eq.). The mixture was agitated and cooled to between -5C and 5C. The reaction mixture was slowly charged with triflouroacetic acid (117 kg, 7.5 eq.). The reaction mixture was warmed to a temperature between 20C and 30C and stirred for 12 to 15 hours. The reaction mixture was quenched by slow addition of an aqueous solution of 10% sodium carbonate (486 L, 0.5 eq.) at a temperature between 5C and 15C. The organic layer was separated and the aqueous layer extracted with methylene chloride (19 L). A mixture of acetone (456 L), water (56.4 L), and L-tartaric acid (22.6 kg, 1.1 eq.) was prepared in a second reactor. The tartaric acid mixture was combined with the organic layers at a temperature between 20C and 25C. The resulting slurry was heated to a temperature between 35C and 45C and stirred for 8 to 18 hours (overnight). When the reaction was judged to be complete, the slurry was cooled and granulated at a temperature between 0C and 10C for three to four hours and filtered. The product cake was washed with a mixture of acetone (40 L) and water (4.5 L). The product was dried under vacuum using only mild heat (applied if evaporation of acetone results in cooling). A yield of 37.7 kg of (3aR)-2,3a,4,5,6,7-hexahydro-2-methyl-3a-(phenylmethyl)-3H-pyrazolo[4,3-c]pyridin-3-one, (2R,3R)-2,3-dihydroxybutanedioate (1:1) was obtained (70.1% yield).

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, 193274-02-1, tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate.

Reference:
Patent; Pfizer Products Inc.; EP1031575; (2000); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58602-02-1, 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. 58602-02-1, name is 2,6-Difluoro-3-nitropyridine, molecular formula is C5H2F2N2O2, 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-(Ethylamino)-6-fluoro-3-nitropyridine To a solution of 2,6-difluoro-3-nitropyridine (45.7 g, 285 mmol) in THF (500 mL) at -40 C. was added drop-wise a solution of ethylamine (25.7 g, 570 mmol) in THF (250 mL). After 30 min, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The resulting yellow solid was purified by flash chromatography (15% EtOAc in hexane) to give the title compound (43.2 g, 82% yield) as a yellow solid.

According to the analysis of related databases, 58602-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Simoneau, Bruno; US2002/28807; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89466-17-1, 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 89466-17-1, name is 6-Bromo-5-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 0.052 g ammonium chloride (1 mmol) in 4 mL water or methanol was added isocyanide (1.2 mmol), aromatic aldehyde (1.1 mmol), and 2-aminopyridine (1 mmol) and sealed in stainless steel autoclave with a Teflon-coated, and then the autoclave was put in the oven at 75oC in 2 h. The autoclave was taken out and cooled to room temperature. The reaction mixture was put into 30 mL cooled water to afford the product as a precipitate. The solid residue was filtered and crystallized from ethyl acetate to give products.

According to the analysis of related databases, 89466-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Xiaohui; Shang, Qianqian; Bo, Caiying; Hu, Lihong; Zhou, Yonghong; Arkivoc; vol. 2018; 5; (2018); p. 184 – 193;,
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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5F3N2O

General procedure: N,N-Dimethylformamide (2 mL), triethylamine (0.079 mL, 0.57 mmol) and 1- [bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-]pyridinium 3-oxid hexafluorophosphate (79 mg, 0.208 mmol, HATU) were added to a mixture of the product of Example 18A (59.4 mg, 0.189 mmol) and (5-(difluoromethoxy)pyridin-2-yl)methanamine (Enamine, 33 mg, 0.189 mmol) in sequential order. The reaction mixture was then stirred at ambient temperature for 30 minutes. The resulting solution was filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt CI 8 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 90 mL/minute, 5-100% gradient of acetonitrile in buffer (0.025 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to give the title compound (56 mg, 0.119 mmol, 63% yield). JH NMR (501 MHz, DMSO-de) delta ppm 8.73 (s, 1H), 8.44 (t, J = 6.1 Hz, 1H), 8.40 (d, J = 2.8 Hz, 1H), 7.64 (dd, J = 8.6, 2.9 Hz, 1H), 7.50 (t, J = 8.9 Hz, 1H), 7.29 (dd, J = 8.6, 0.7 Hz, 1H), 7.27 (t, J = 73.5 Hz, 1H), 7.08 (dd, J = 11.4, 2.9 Hz, 1H), 6.86 (ddd, J = 8.9, 2.9, 1.2 Hz, 1H), 4.47 (s, 2H), 4.33 (d, J = 6.1 Hz, 2H), 2.22 (s, 6H); MS (ESI+) m/z 470 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 105166-53-8, [2,2′-Bipyridin]-3-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 105166-53-8, blongs to pyridine-derivatives compound. Product Details of 105166-53-8

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105166-53-8, [2,2′-Bipyridin]-3-amine, and friends who are interested can also refer to it.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
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.6854-07-5, name is 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, molecular formula is C6H4N2O5, molecular weight is 184.11, as common compound, the synthetic route is as follows.Recommanded Product: 6854-07-5

Step B 2-Methoxy-3-carbomethoxy-5-nitropyridine 2-Hydroxy-3-carboxy-5-nitropyridine was converted to 2-chloro-3-chlorocarbonyl-5-nitropyridine in situ and converted to the title compound by reaction with anhydrous methanol according to the procedure of A. Monge et al J. Het. Chem. (29), 1545 (1992). In a 500 mL was added starting material (10.2 g, 54 mmol) in 200 mL of chlorobenzene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6854-07-5, 5-Nitro-2-oxo-3-pyridinecarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US5750549; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62674-71-9 ,Some common heterocyclic compound, 62674-71-9, molecular formula is C6H6IN, 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.

General procedure: Pyridines substituted at the 2-position with halides shown in Tables 2 and 3 are stirred in a mixture of toluene (900 mL) and anhydrous ether (600 mL). The resulting solutions were cooled to < -100 °C for 20 min at which point n-BuLi/hexane was added slowly over 22 min. After maintaining the temperature below -100 °C for 20 min, triisopropylborate was added dropwise, and then the reaction mixture was stirred below -70 °C. After stirring for 4 h, ether (500 mL) was added and the solution was allowed to stand overnight at room temp. Isopropanol was added (30mL), then the reaction mixture was stirred for 30 min, the allowed to stand without stirring for an additional 2 h. The resulting precipitate was collected by filtration then washed with ethyl ether and dried under nitrogen atmosphere for 1.5 h. The resulting triisopropoxy analog was treated with a mixture of acetone and water (450 mL/50 mL) to remove any contaminating n-butylborate lithium salt. The solids were collected by filtration, washed with acetone/water (9:1, 300 mL), and dried in air for 2h, then lyophilized overnight to afford product. 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. 62674-71-9, 2-Iodo-6-methylpyridine, other downstream synthetic routes, hurry up and to see. Reference:
Article; Chen, Kuanchiang; Peterson, Richard; Math, Shivanand K.; Lamunyon, James B.; Testa, Charles A.; Cefalo, Dustin R.; Tetrahedron Letters; vol. 53; 36; (2012); p. 4873 – 4876;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem