Category: pyridine-derivatives

Reference of 97004-04-1, 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 97004-04-1 as follows.

2-(4-Trifluoromethylphenyl hydrazono) propionic acid (12.31 g, 50.0 mmol) was dissolved in dichloromethane (250 ml) and N,N-dimethylformamide (25 ml), and 5-aminomethyl-2-chloropyridine (7.13 g, 50.0 mmol) and 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloric acid salt (9.59 g, 50.0 mmol) were added thereto. 30 hours later, the mixture was washed with 1N hydrochloric acid, a saturated sodium bicarbonate water and a saturated brine, and dried on sodium sulfate and then filtrated. The residue obtained by concentrating the resulting filtrate was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-2-(4-trifluoromethylphenyl hydrazono) propionic acid amide (Compound No. 63) (14.47 g, 39.02 mmol, 78%). Compound No. 63: mp 184C; 1H NMR (400 MHz, CDCl3) delta 2.16 (3H, s), 4.57 (2H, d), 7.15 (2H, d), 7.31 (2H, d), 7.35 (1H, brt), 7.54 (2H, d), 7.64 (1H, s), 7.66 (1 H, dd), 8.38 (1 H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97004-04-1, its application will become more common.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; EP1470752; (2004); A1;,
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.75358-90-6, name is Ethyl 2-cyanonicotinate, molecular formula is C9H8N2O2, molecular weight is 176.17, as common compound, the synthetic route is as follows.Recommanded Product: 75358-90-6

To a solution of ethyl 2-cyano-3-pyridinecarboxylate (2.5 g) and conc. HCl (5 mL) in 150 mL ethanol was added 10% Pd/C (wet, 250 mg) and the reaction mixture was hydrogenated using a hydrogen balloon and stirred for 12 h. The reaction was filtered through celite and ethanol was evaporated to give ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCl as a white solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75358-90-6, Ethyl 2-cyanonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Global Blood Therapeutics, Inc.; The Regents of the University of Califorina; Cytokinetics, Inc.; Metcalf, Brian; Chuang, Chihyuan; Warrington, Jeffrey; Paulvannan, Kumar; Jacobson, Matthew P.; Hua, Lan; Morgan, Bradley; US2015/344483; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 709652-82-4, 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below.

To a stirred solution of compound 2 (4.6 g) in HC1 (48.4 mL ) was added sodium nitrite ( 5.3 mL ) dropwise at-5 C. The reaction mixture was stirred at room temperature for 2h. The resulting solids were collected by filtration and dried in vacuum to give compound 3 (4.4 g, 88%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,709652-82-4, 2-Amino-5-bromonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VITAS PHARMA RESEARCH PRIVATE LIMITED; RANGARAJAN, Radha; KUMAR, Rajinder; PRABHAKAR, B V; CHANDRASEKHAR, P; MALLIKARJUNA, P; BANERJEE, Ankita; WO2013/42035; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 34486-24-3, Adding some certain compound to certain chemical reactions, such as: 34486-24-3, name is 2-Amino-6-(trifluoromethyl)pyridine,molecular formula is C6H5F3N2, 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 34486-24-3.

To a stirred solution of 6-(trifluoromethyl)pyridin-2-amine (2 g, 12.34 mmol) in methanol (20 ml.) was added N-bromosuccinamide (2.19 g, 12.34 mmol) in portions at 0 C. Reaction mixture was then stirred at rt for 10 h. After completion of reaction (monitored by TLC) evaporated the solvent invacuo to dryness. Crude compound was purified by column chromatography using 0-50% EtOAc in n-hexanes to afford title compound 1 .4 g (48.2%), Rf = 0.55 (20% EtOAc in n-Hexane). 1 H NMR (300 MHz, Chloroform-d) d 7.68 (d, J = 8.6 Hz, 1 H), 6.53 (d, J = 8.7 Hz, 1 H), 4.71 (s, 2H).

According to the analysis of related databases, 34486-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; NG, Shuyi Pearly; RAO, Srinivasa P S; (126 pag.)WO2019/244049; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 169205-95-2, 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.169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, molecular weight is 166.2, as common compound, the synthetic route is as follows.

Preparation of fert-Butyl [2-([l ,3]oxazolo[4,5-]pyridin-2-ylamino)ethyl]carbamate(P^ />-NH(CH2)2NHBOCA mixture of 2-(methylthio)-[l,3]-thiazolo[4,5-&]pyridine (100 mg, 0.602 mmol) and /erf-butyl (2-aminoethyl)carbamate (193 mg, 1.204 mmol) was heated neat at 85C for 1 h. The reaction mixture was cooled to room temperature, the residue obtained was purified by silica gel column chromatography using 2% methanol in chloroform as eluent to give the title compound as an off-white solid; 1.40 (s, 9H), 3.45-3.52 (m, 2H), 3.65- 3.70 (m, 2H), 6.90-6.96 (m, IH), 7.45 (d, J = 7.2 Hz, IH), 8.17-8.23 (m, IH); ESI- MS (m/z) 279.11 (MH)+.

Statistics shows that 169205-95-2 is playing an increasingly important role. we look forward to future research findings about 2-(Methylthio)oxazolo[4,5-b]pyridine.

Reference:
Patent; GLENMARK PHARMACEUTICAL S.A.; IRLAPATI, Nagoswara, Rao; THOMAS, Abraham; KURHE, Deepak, Kantilal; SHELKE, Sandeep, Yadunath; KHAIRATKAR, JOSHI, Neelima; VISWANADHA, Srikant; MUKHOPADHYAY, Indranil; WO2010/10435; (2010); A2;,
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. 1186663-33-1, name is Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

[00253] 1C. (Z)-Ethyl 5-( ,N’-bis(tert-butoxycarbonyl)carbamimidoyl)-4,5,6,7- tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate: 5-tert-Butyl 2-ethyl 6,7- dihydrothiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate (0.500 g, 1.601 mmol) was treated with HC1 (4.0M in dioxane) (20.01 ml, 80 mmol) at room temperature. After 1 h, the precipitate was filtered, washed with Et20, and dried in vacuo. The amine hydrochloride salt was dissolved in DMF (10 mL) and treated with DIPEA (1.677 ml, 9.60 mmol) and (E)-tert-butyl (((tert-butoxycarbonyl)amino)( lH-pyrazol- 1 -yl)methylene)carbamate (0.497 g, 1.601 mmol). After 14 h, the reaction mixture was taken up in EtOAc (50 mL) and washed with water. The water layer was extracted with additional EtOAc. The combined organic layers were washed with 1.0M HQ solution, water, brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by column chromatography to give 1C (0.282 g, 38.8 % yield) as a white solid. MS (ESI) m/z: 455 (M+H)+.

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, 1186663-33-1, Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate hydrochloride.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; ORWAT, Michael J.; SMITH II, Leon M.; EWING, William R.; WO2014/59202; (2014); A1;,
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.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.SDS of cas: 66909-38-4

Example 406-TERT-BUTYL-N-((1R)-1-{4-METHYL-5-[(METHYLSULFONYL)AMINO]PYRIDIN-2-YL}ETHYL)-2-NAPHTHAMIDE 40A) N-(6-CHLORO-4-METHYLPYRIDIN-3-YL)METHANESULFONAMIDE A mixture of 3-amino-6-chloro-4-picoline (2.0 g, 14.0 mmol) and methanesulfonyl chloride (1.93 g, 16.8 mmol) in pyridine (140 ml) was stirred for 2 hours at room temperature. The resulting mixture was quenched with 2 M HCl aqueous solution and diluted with EtOAc. The separated organic phase was washed with 2 M HCl aqueous solution, dried over magnesium sulfate, concentrated to give crude. It was diluted with EtOAc and extracted with 2 M sodium hydroxide aqueous solution. The separated basic phase was acidified with 2 M HCl aqueous solution to give precipitates, which were collected and rinsed with water, dried in vacuo to afford the title compound (2.42 g, 78%) as a solid.1H NMR (DMSO-d6) delta 2.33 (3H, s), 3.05 (3H, s), 7.47 (1H, s), 8.24 (1H, s), 9.44 (1H, brs).MS (ESI): m/z 221 (M+H)+, 219 (M-H)-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66909-38-4, 6-Chloro-4-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; RENOVIS, INC.; US2012/88746; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 5006-66-6, name is 6-Oxo-1,6-dihydropyridine-3-carboxylic acid, molecular formula is C6H5NO3, 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. Safety of 6-Oxo-1,6-dihydropyridine-3-carboxylic acid

(d) 6-Hydroxynicotinic acid methyl ester (212) A suspension of 6-hydroxynicotinic acid (10.0 g, 71.9 mmol) in anhydrous CH2Cl2 (80 mL, plus 3 drops of DMF) was purged with nitrogen, cooled to 0 C., and treated with oxalyl chloride (7.53 mL, 86.3 mmol). After 18 h at room temperature, excess methanol was cautiously added. The reaction was evaporated and chromatographed (20% EtOAc in hexanes) to provide 2.74 g (25%) of the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 5006-66-6.

Reference:
Patent; Bigge, Christopher Franklin; Bridges, Alexander James; Casimiro-Garcia, Agustin; Fakhoury, Stephen Alan; Lee, Helen Tsenwhei; Reed, Jessica; Schaum, Robert; Schlosser, Kevin Matthew; Sexton, Karen; Zhou, Hairong; US2003/171377; (2003); 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. 89282-03-1, name is 3-Iodopyridin-4-ol, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

The synthetic route of 89282-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Hee Jung; Kim, Ji-Eun; Yum, Eul Kgun; Kim, Young Hoon; Han, And Chang-Woo; Bulletin of the Korean Chemical Society; vol. 36; 1; (2015); p. 211 – 218;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 178876-83-0, 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. 178876-83-0, name is Methyl 6-amino-3-bromopicolinate. A new synthetic method of this compound is introduced below.

At 0 C., to a solution of NOBF4 (2.28 g, 19.52 mmol) in dichloromethane (60 mL) was added a solution of methyl 6-amino-3-bromopyridine-2-carboxylate (3.45 g, 14.93 mmol) in dichloromethane (15 mL) slowly. The resulting solution was stirred at room temperature for 16 h. The reaction mixture was then quenched by water (100 mL) and extracted with dichloromethane (120 mL*2). The combined organic phase was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with petroleum ether: ethyl acetate (10:1 to 7:3 gradient) to yield methyl 3-bromo-6-fluoropyridine-2-carboxylate (2.4 g, 69%) as light yellow oil. MS: m/z=233.8 [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,178876-83-0, its application will become more common.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem