Category: pyridine-derivatives

Synthetic Route of 1214353-79-3, Adding some certain compound to certain chemical reactions, such as: 1214353-79-3, name is Methyl 5-bromo-6-chloropicolinate,molecular formula is C7H5BrClNO2, 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 1214353-79-3.

Example 92 – Preparation of Intermediate 28 [ 00385] The synthesis of Intermediate 28 followed General Procedure 20 following. General Procedure 20 Intermediate 27 Intermediate 28 [ 00386 ] To a dry round-bottomed flask pre-cooled to 0C and under N2 gas flow, NaH (0.56 g, 14.0 mmol, 3.5 eq) was added. To this was slowly added methoxyethanol (10.0 mL) dropwise, and the mixture was stirred for 30 minutes. To this was added methyl-5-bromo-6-chloropyridine-2-carboxylate (Intermediate 27, 1.0 g, 4.0 mmol, 1.0 eq) portionwise. The reaction mixture was then stirred at ambient temperature and then heated at 100C for 10 minutes. After completion (monitored by TLC and LC-MS), the reaction mixture was concentrated under reduced pressure to obtain a brown solid residue, which was slowly quenched with acetic acid. The mixture was extracted with 10% MeOH : dichloromethane, dried over sodium sulfate and concentrated to give the desired product 5-bromo-6-(2- methoxyethoxy) pyridine-2-carboxylic acid (Intermediate 28, 0.70 g, yield-63%) m/z 278.28 [M+2]+; 1H NMR (400 MHz, DMSO) delta 13.41 (s, 1H), 8.19 (d, J = 7.8 Hz, 1H), 7.56 (d, J = 7.8 Hz, 1H), 4.52 (dd, J = 5.4, 3.8 Hz, 2H), 3.71 (dd, J = 5.4, 3.8 Hz, 2H), 3.33 (s, 3H) ppm.

According to the analysis of related databases, 1214353-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; KITA, David Ben; ESTIARTE-MARTINEZ, Maria de los Angeles; PHAM, Son Minh; (244 pag.)WO2016/44662; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-72-0, 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 1620-72-0, name is 2-Methyl-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-methyl-6-(trifluoromethyl)pyridine (100 mg, 0.620 mmol) was dissolved in CC14 (3 mL), and N-bromosuccinimide (NBS) (110 mg, 0.620 mmol) and 1,1′- azobis(cyclohexanecarbonitrile) (VAZO, 8 mg, 0.031 mmol) were added thereto, followed by heating and stirring at 90 C for 15 hrs. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by MPLC (Hex/EA = 5:1) to obtain the title compound as white solid (42.5 mg, yield: 28.4%). 1H NMR (300MHz, CDC13) delta 4.60 (2H, s), 7.61 (1H, d), 7.68 (1H, d), 7.90 (1H, t)

According to the analysis of related databases, 1620-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK CHEMICALS CO., LTD.; KIM, Seon-Mi; KIM, Jae-Sun; LEE, Minhee; LEE, So-Young; LEE, Bong-Yong; SHIN, Young Ah; PARK, Euisun; LEE, Jung A; HAN, Min-Young; AHN, Jaeseung; YOO, Taekyung; KIM, Hun-Taek; WO2013/129879; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 571189-49-6 ,Some common heterocyclic compound, 571189-49-6, molecular formula is C10H16N4, 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 Compound 50 0.060 g (0.205 mmole) was added 5-(4-methylpiperazin-1-yl)pyridin- 2-amine (35.42 mg, 0.9 eq) followed by the addition of 1,4-dioxane (3 mL). After degassing with nitrogen, Pd2dba3 (12 mg), BINAP (16 mg) and sodium tert-butoxide (24 mg) were added.The contents were then heated at 90 degrees in a CEM Discovery microwave for 3 hrs. Thereaction was then loaded onto a silica gel column and purified by eluting with DCM/MeOH (0-15%). ?HNMR (600 MHz, DMSO-d6) oe ppm 0.75 (t, J7.47 Hz, 3 H) 0.91 (d, J6.73 Hz, 3 H)1.04 – 1.20 (m, 2 H) 1.80 – 1.98 (m, 1 H) 2.77 (d, J=3.81 Hz, 3 H) 2.94 – 3.90 (m, 10 H) 4.54 -4.68 (m, 1 H) 7.06 – 7.23 (m, 2 H) 7.56 – 7.75 (m, 1 H) 7.90 – 8.12 (m, 2 H) 8.29 (s, 1 H) 9.07 (s,1 H) 10.98- 11.74(m,2H). LCMS(ESI)435(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. 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; BISI, John, Emerson; ROBERTS, Patrick, Joseph; SORRENTINO, Jessica, Ann; (304 pag.)WO2016/40848; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1462-86-8, 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.1462-86-8, name is 3-Aminopicolinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

Step B. 2-(I-Naphthalenyl)-H-pyrido[3,2-d][1,3]oxazin-4-one; 1-Naphthalenecarbonyl chloride (400 mg, 2.1 mmol) in CH2C12 (2 mL) was added into a solution of 3-amino-2-pyridinecarboxylic acid (277 mg , 2.0 mmol) and diisopropylethylamine (284 mg, 2.2 mmol) in DMF (10 mL) at 0 C. The reaction mixture was allowed to stir overnight at room temperature, and was then treated with diisopropylethylamine (284 mg, 2.2 mmol) and HATU (837 g, 2.2 mmol). After stirring for 1 h at room temperature, the reaction mixture was heated at 50 C to provide the title compound which was used in Step A. MS (ESI) (M+H)+ 274.79

Statistics shows that 1462-86-8 is playing an increasingly important role. we look forward to future research findings about 3-Aminopicolinic acid.

Reference:
Patent; AstraZeneca AB; WO2005/115987; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 886364-86-9, Adding some certain compound to certain chemical reactions, such as: 886364-86-9, name is 5-Bromo-4-methylpicolinonitrile,molecular formula is C7H5BrN2, 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 886364-86-9.

A mixture of 4-chloro-N-(2-hydroxy-phenyl)-N-methyl-3-(4,4,5,5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzamide (100 mg, 0.26 mmol), 5-bromo-4- methyl-pyridine-2-carbonitrile (61 mg, 0.31 mmol), Pd(PPh3)4 (15 mg, 0.013 mmol), K2CO3 (90 mg, 0.65 mmol) in dioxane (1.2 mL), was heated at 95 0C for 12 hrs. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and concentrated in vacuo. Silica gel column chromatography (eluent: ethyl acetate/hexane(1/4 up to 4/1 )) yielded 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2- hydroxy-phenyl)-N-methyl-benzamide 8-1 (68 mg).

According to the analysis of related databases, 886364-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2008/124610; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1142194-24-8, 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.1142194-24-8, name is 4-Bromo-2-isopropoxypyridine, molecular formula is C8H10BrNO, molecular weight is 216.08, as common compound, the synthetic route is as follows.

General procedure: To 1.76 mmol of the appropriate amine in 10 mL dioxane are added 1.76 mmol pyridyl halide, 7.02 mmol NaOtBu, 0.70 mmol 2-(di-tert-butylphosphino)biphenyl and 0.18 mmol Pd2(dba)3. The mixture is degassed thoroughly and stirred at 45 C over night. The reaction mixture is filtered, the solvent removed in vacuo and the residue is purified by HPLC.

The chemical industry reduces the impact on the environment during synthesis 1142194-24-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 771579-27-2 ,Some common heterocyclic compound, 771579-27-2, molecular formula is C8H12N2O, 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.

g) 6-bromo-N-((l,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-l-isopropyl-3-methyl-lH- indazole-4-carboxamideTo a stirred solution of 6-bromo-l-isopropyl-3-methyl-lH-indazole-4-carboxylic acid, 1 (6.5 g, 21.88 mmol) in DCM (250 mL) was added EDC HCl (5.01 g, 26.23 mmol), HOBt (3.545 g, 26.20 mmol) followed by diisopropyl ethyl amine (14.1 1 g, 109.37 mmol) and stirred at room temperature for 15 min. To the resulting mixture, 3-(amino methyl)-4,6-dimethylpyridin-2(lH)-one (3.32 g, 21.84 mmol) followed by DMAP (catalytic amount) was added and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was diluted with DCM (300 mL) and washed with IN HC1 solution (250 mL), saturated NaHC03 solution (250 mL) and brine solution. The organic layer was dried over anhydrous Na2S04 , filtered, and concentrated under reduced pressure. The residue was triturated with diethyl ether (100 mL), filtered, and dried to afford 6-bromo-N-((l,2-dihydro-4,6- dimethyl-2-oxopyridin-3-yl)methyl)-l-isopropyl-3-methyl-lH-indazole-4-carboxamide as an off white solid (5.5 g, 58 %). :H NMR (DMSO-d6, 400 MHz): delta 1.412 (d, J = 6.4 Hz, 6H), 2.1 12 (s, 3H), 2.215 (s, 3H), 2.383 (s, 3H), 4.319 (d, J = 5.2 Hz, 2H), 4.907 – 4.972 (m, 1H), 5.864 (s, 1H), 7.129 (d, J = 1.2 Hz, 1H), 8.01 1 (d, J = 1.2 Hz, 1H), 8.473 (t, J = 5 Hz, 1H), 11.479 (brs, 1H). LCMS (ES+): 431.02 [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. 771579-27-2, 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; DUQUENNE, Celine; JOHNSON, Neil; KNIGHT, Steven, D.; LaFRANCE, Louis; MILLER, William, H.; NEWLANDER, Kenneth; ROMERIL, Stuart; ROUSE, Meagan, B.; TIAN, Xinrong; VERMA, Sharad, Kumar; WO2011/140325; (2011); 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. 112575-13-0, name is 6-Bromo-N,N-dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-N,N-dimethylpyridin-2-amine

b (3R,4S)-4-[4-(6-Dimethylaminopyridin-2-yl)phenoxy]-1-pyridin-3-ylpentan-3-ol Prepared according to the method described in Example 15g) from toluene (4 ml), 2M aqueous sodium carbonate (0.5 ml), (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-yl-butoxy]benzeneboronic acid (0.200 g, Example 15f)), ethanol (1 ml), 6-bromo-2-N,N-dimethylaminopyridine (0.201 g, Example 18a)) and tetrakis(triphenylphosphine)palladium(0) (0.020 g) with heating at 120 C. for 4 hours. The product was purified by normal-phase HPLC eluding with a gradient of 0-25% ethanol in dichloromethane to give the title compound as an oil (0.091 g). MS (APCI) 378 (M+H)+ 1 H NMR (DMSO) 8.43(1H, s); 8.38(1H, d); 7.95(2H, d); 7.63(1H, d); 7.52(1H, t); 7.32-7.27(1H, m); 7.04(1H, d); 6.95(2H, d); 6.52(1H, d); 4.98(1H, d); 4.37-4.29(1H, m); 3.60-3.51(1H, m); 3.08 (6H, s); 2.84-2.76(1H, m); 2.69-2.61(1H, m); 1.91-1.81(1H, m); 1.69-1.58(1H, m); 1.24(3H, d).

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, 112575-13-0, 6-Bromo-N,N-dimethylpyridin-2-amine.

Reference:
Patent; AstraZeneca UK Limited; US6143751; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 34941-91-8, 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 34941-91-8 as follows.

Step A: 2-Chloro-4-i uoropyridine~3~carboxylic acid (64-2)A solution of LDA (97 ml, 1.8 M heptane/THF/ethylbenzene, 175 mmol) and THF (304 ml) were combined and cooled to -78C. 2-Chloro-4-fluoropyridine (20.0 g, 152 mmol) was dissolved in 50 ml THF and then added dropwise over 20 minutes and then the solution was stirred for 1 hour. The reaction was poured onto dry ice and -the dry ice was allowed to evaporate. Water and 1 N NaOH were added to the residue. The mixture was extracted with Et20 and the organic layer discarded. The aqueous was acidified with 1 N HC1 and then extracted with EtOAc. The organic portion was washed with brine, dried (MgS04) and concentrated to give 64^2 (19 g, 71.2%) as an orange solid. MS (ESI): m/z = 176.0 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34941-91-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BUNGARD, Christopher, James; PERKINS, James, J.; MANIKOWSKI, Jesse, J.; DE LEON, Pablo; MEISSNER, Robert, S.; WO2011/53574; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride, 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, Recommanded Product: 2-(Pyridin-2-yl)acetic acid hydrochloride, blongs to pyridine-derivatives compound. Recommanded Product: 2-(Pyridin-2-yl)acetic acid hydrochloride

Step 4. N-(6-(6-chloro-5-(-isopropylamino)pyridin-3-yl)benzo[d1thiazol-2-yl)-2-(pyridin-2-yl)acetamide; 6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2 -amine (121.8 mg, 0.382 mmol) and HATU (215.9 mg, 0.568 mmol) were suspended in DCM (2.9 ml) and diisopropylethylamine (0.21 ml, 1.2 mmol) and 2-pyridylacetic acid hydrochloride (94.3 mg, 0.543 mmol) were added. The reaction was stirred under nitrogen at room temperature overnight, concentrated and purified on a silica gel column (20: 1 DCM / MeOH). Fractions with product were collected, concentrated, and purified on HPLC (10% to 100% MeCN / water with 0.1 % TFA over 30 minutes). Fractions with product were collected, concentrated, and dried under high vacuum in a water bath (~ 50 C), then at room temperature overnight to afford N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)-2-(pyridin-2-yl)acetamide (57.5 mg, 34% yield). MS (ESI pos. ion) m/z: 438. Calculated exact mass for C22H20ClN5OS 437.

The synthetic route of 16179-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem