Category: pyridine-derivatives

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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.SDS of cas: 866775-18-0

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A step 4) (300 mg, 1.003 mmol), N,N-dimethylprop-2-yn-1- amine (0.1 19 ml, 1.104 mmol) and copper(l) iodide (3.82 mg, 0.020 mmol) in 1 ,4- dioxane (1.500 ml) under nitrogen was treated with triethylamine (1.818 ml, 13.04 mmol) followed by Pd(PPh3)2CI2 (14.08 mg, 0.020 mmol) and stirred at 100C for 15 minutes. A further portion of Pd(PPh3)2CI2 (14.08 mg, 0.020 mmol) was added and stirring continued at 100C for 15 minutes. The mixture was poured into water and extracted with EtOAc. The organic portion was separated and washed with water, brine and dried using a phase separating column. The mixture was acidified to pH1 using 1 M HCI and the aqueous portion was separated and basified to pH7 using saturated sodium bicarbonate solution. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine and dried using a phase separating column. The solvent was removed under reduced pressure to afford the title compound; LC-MS Rt = 0.51 min [M+H]+ 302.4 ; Method 2minl_owpH.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren, Mark; WO2013/38381; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1167056-96-3 ,Some common heterocyclic compound, 1167056-96-3, molecular formula is C7H4BrClN2, 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 compound 221.4 (l . lg, 7.2mmol, l .Oeq) in dimethylformamide (20mL) at 0C, sodium hydride (0.5mL, 10.8mmol, 1.5eq) was added. Reaction mixture was stirred at 0C for 20min. Then, ethyl iodide (1.6mL, 10.8mmol, 1.5eq) was added. Reaction mixture was stirred at room temperature for 3h. After completion of the reaction, the reaction mixture was transferred into water to obtain the precipitate which was filtered, washed with water and dried well under vacuum to obtain 221.5. (0.9g, 12.91%). MS(ES): m/z 260.37 [M]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1167056-96-3, its application will become more common.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 72141-44-7 , The common heterocyclic compound, 72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, 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.

(e); 10.0 g (69.9 mmol) of crude 4-chloro-2-methoxypyridine obtained in Step (d) was dissolved in 100 ml of dimethylformamide, and 37.2 g (279 mmol) of N-chlorosuccinimide was added, followed by stirring at room temperature for 12 hours. 400 ml of water was added to terminate the reaction, followed by extraction with ethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 9.10 g (crude yield: 73%) of crude 4,5-dichloro-2-methoxypyridine. 1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.90(s, 3H), 6.85(s, 1H), 8.14(s, 1H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1452-94-4, Adding some certain compound to certain chemical reactions, such as: 1452-94-4, name is Ethyl 2-chloronicotinate,molecular formula is C8H8ClNO2, 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 1452-94-4.

A toluene solution (300 mL) of ethyl 2-chloronictinate (5.57 g), phenylboronic acid (4.76 g), tripotassium phosphate (8.91 g), 1,1′-bis (diphenylphosphino) ferrocene-palladiumdichloride dichloromethane complex (439 mg) was stirred under reflux for 4 hours in a nitrogen atmosphere. Water (100 mL) was added to the reaction solution, and the reaction solution was separated. The obtained organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified with silica gel column chromatography (hexane/ethyl acetate=96/4 to 75/25) to give ethyl 2-phenylnicotinate (5.27 g) as an oil. MS m/z 229 [M+H]

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. 1452-94-4, Ethyl 2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; SUMITOMO DAINIPPON PHARMA CO., LTD.; FUSANO, Akira; KOBAYASHI, Tomonori; SAITO, Yasuhiro; KANAI, Toshio; (55 pag.)US2016/221948; (2016); 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. 130284-52-5, name is 6-Bromo-5-chloropyridin-3-amine, molecular formula is C5H4BrClN2, 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. name: 6-Bromo-5-chloropyridin-3-amine

Pd2(dba)3 (176.56 mg, 0.19 mmol) and Xphos (183.83 mg, 0.39 mmol) were added to a solution of 6-bromo-5-chloropyridin-3-amine (800 mg, 3.86 mmol), 1 -methyl-3-(4,4,5,5-tetramethyl-i ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1203.52 mg, 5.78 mmol) and K3P04 (2.456 g,11.57 mmol) in dioxane/H20 (6/1, 20 mE) under an N2 atmosphere. The mixture was stirred at 1000 C. overnight. The reaction solution was filtered and the filtrate was concentrated to give a crude product. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 0/100). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford 1 57a (530 mg, 5 9.0% yield) as a yellow solid. ECMS (ESI) mlz M+i: 209.1.

With the rapid development of chemical substances, we look forward to future research findings about 130284-52-5.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55052-27-2 ,Some common heterocyclic compound, 55052-27-2, molecular formula is C7H5ClN2, 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.

At room temperature, concentrated aqueous ammonia (40 mL) was added drop-wise to 6-chloro-7-azaindole (3.20 g, 0.024mol), after the tube is heated, the reaction is heated at 120 C for 5h. The reaction is complete, cooling, filter and then obtained a brown solid product (2.00 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55052-27-2, its application will become more common.

Reference:
Patent; Ding Min; (8 pag.)CN108997343; (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. 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7ClN2O

To a solution of XII-1 (0.50 g, 1 .97 mmol) in pyridine (10 mL) was added X-1 (0.18 g, 1 .25 mmol) and DMAP (0.012 g, 0.09 mmol). The reaction mixture was heated at 80 C for 16h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under vacuum. The residue was diluted with H20 (100 mL), 1 N HCI (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated under vacuum. The crude obtained was purified by column chromatography (silica, 100-200 mesh, 40% EtOAc in hexane) to afford 6-chloro-N-(2,5-difluoropyridin-3-yl)-1H-indole-3-sulfonamide 1-1 (0.05 g) as an off-white solid. (1207) Yield: 7%. (1208) Basic LCMS Method 1 (ES ): 342 (M-H)-, 97% purity. (1209) 1H NMR (400 MHz, DMSO-cfe) d 7.25 (dd, J=8.31 , 1.47 Hz, 1 H), 7.54 (s, 1 H), 7.71-7.81 (m, 2H), 7.89 (s, 1 H), 8.16 (d, J=2.93 Hz, 1 H), 10.73 (brs, 1 H), 12.22 (brs, 1 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, 1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine.

Reference:
Patent; UCB PHARMA GMBH; PEGURIER, Cecile; PROVINS, Laurent; CARDENAS, Alvaro; LEDECQ, Marie; MUELLER, Christa E.; HOCKEMEYER, Joerg; EL-TAYEB, Ali; BOSHTA, Nader; RASHED, Mahmoud; (165 pag.)WO2019/243303; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde, molecular formula is C6H4ClNO, 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.

5.1.96 EXAMPLE 96: SYNTHESIS OF 2-(5-CHLOROPYRIDIN- 3-YL)-8-OXO-9-(2-(TRIFLUOROMETHYL)PHENYL)-8,9-DIHYDRO-7H-PURINE-6-CARBOXAMIDE; EPO [00432] A. Z-CS-Chloropyridin-S-yO-S-oxo^-CZ^trifluoromethyOphenyO-S^- dihydro-7H-purine-6-carboxamide. (Z)-l-(2-Amino-l ,2-dicyanovinyl)-3-(2- (trifluoromethyl)phenyl)urea {See Example 50.A) (0.15 g, 0.51 mmol), 5- chloronicotinaldehyde (0.14 g, 0.99 mmol), and triethylamine (0.10 ml, 0.72 mmol) were combined in methanol (7.0 mL) and stirred at room temperature overnight. Excess solvent was removed under reduced pressure and the resulting residue was purified by reverse-phase preparatory HPLC (30-80% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). Clean fractions were neutralized with ammonium hydroxide and solvent removed under reduced pressure. The resulting material was taken up in ethyl acetate, washed successively with potassium carbonate, water, and brine. The solution was dried over sodium sulfate, filtered and solvent removed under reduced pressure to provide the product as an off white solid (0.035 g, 0.08 mmol, 16% yield). 1H NMR (400 MHz, DMSO-^5) delta 12.07 (bs, IH), 9.23 (s, IH), 8.95 (s, IH), 8.59 (m, 2H), 7.93 (m, 2H), 7.78 (m, 2H), 7.63 (bs, IH); MS (ESI) m/z 435.0 [M+l]+; mp 230-2320C.

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 113118-82-4, 5-Chloronicotinaldehyde.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1160791-13-8, 2-Amino-6-bromothiazolo[5,4-b]pyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

General procedure: The mixture of 6-bromobenzo[d]thiazol-2-amine (2.0 g, 8.73 mmol), carbonyldimidazole (4.24 g, 26.2 mmol) and dried DMF (20 ml) was stirred at room temperature for 8 h, added cyclopropanamine (0.76 g, 13.2 mmol), then stirred at room temperature for another 8 h. The volatile was removed under reduced pressure. Water (30 ml) was added to the residue. The resulting suspension was stirred. After standing, the solid was collected by filtration, dried to produce 8a (1.77 g, 65%) as white solid. 4.1.1.9 1-(6-Bromothiazolo[5,4-b]pyridin-2-yl)-3-(2-(morpholinoethyl)urea (8i) White solid; Yield 86%; mp: 152-154 C; 1H NMR (DMSO-d6) delta 11.13 (s, 1H, NH), 8.01 (d, J = 8.3 Hz, 1H, Ar-H), 7.48 (d, J = 8.4 Hz, 1H, Ar-H), 6.81 (s, 1H, NH), 3.60 (s, 4H, OCH2*2), 3.29 (d, J = 5.2 Hz, 2H, CH2), 2.41 (s, 6H, NCH2*3). MS (ESI, m/z): Calcd for [M+H]+ C13H17BrN5O2S: 386, 388, found 386, 388.

The synthetic route of 1160791-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Xiao-Xiao; Li, Huan; Wang, Juan; Mao, Shuai; Xin, Min-Hang; Lu, She-Min; Mei, Qi-Bing; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6477 – 6485;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18699-87-1, Adding some certain compound to certain chemical reactions, such as: 18699-87-1, name is 2-Methyl-3-nitropyridine,molecular formula is C6H6N2O2, 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 18699-87-1.

Into a 5000 mL 3-necked roundbottom flask, was placed a solution of 2-methyl-3-nitropyridine (500 g, 3.26 mol) in DMF (2500 mL). To the mixture was added dimethoxy-N,N-dimethylmethanamine (1350 g, 11.33 mol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 115 C in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 650 g (crude) of N,N-dimethyl-2-(3- nitropyridin-2-yl)ethenamine as red oil.

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. 18699-87-1, 2-Methyl-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem