Day: March 7, 2022

Application of 885326-88-5, 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 885326-88-5, name is Methyl 6-amino-4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a microwave tube was added methyl 6-amino-4-bromopicolinate (CAS: 885326-88-5, Vendor: PharmBlock, 231 mg, 1.00 mmol), THF (3 mL) and LiBH4 (2 M in THF, 1 mL, 2.00 mmol). After being stirred at 65 C for 2 hrs under microwave, the reaction was quenched by adding Na2S04 * 10H2O and the mixture was stirred at rt for another hour. Then it was filtered through celite and the filtrate was concentrated to give compound 45a (230 mg) as a crude oil. MS: calc’d 203 (MFP), measured 203 (MH+).

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 885326-88-5, Methyl 6-amino-4-bromopicolinate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; LIU, Haixia; SHEN, Hong; ZHU, Wei; HU, Taishan; ZHANG, Zhisen; ZHANG, Zhiwei; DEY, Fabian; WANG, Xiaoqing; (89 pag.)WO2019/238629; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23628-31-1, 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. 23628-31-1, name is 6-Aminopicolinic acid, molecular formula is C6H6N2O2, 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.

Example 6. Synthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(2- (trifluoromethyl)phenyl)benzo[d]oxazole-7-carboxamide (Compound 125) : Step 1) Preparation of ethyl 6-aminopicolinate (20): 19 20To a solution of 2-amino-6-pyridinecarboxyric acid (19; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 20 (5.5 g, 76%).

According to the analysis of related databases, 23628-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; VU, Chi, B.; WO2010/19606; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 910656-00-7, 4-Amino-N-methylnicotinamide, 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, HPLC of Formula: C7H9N3O, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9N3O

4-Amino-Lambda/-methyl-3-pyridinecarboxamide (200 mg; may be prepared as described in intermediate 121 ) was dissolved in DMF (20.00 ml_). DMAP (8.08 mg), N,N- diisopropylethylamine (0.462 ml.) and chloroacetyl chloride (0.212 ml.) were added at room temperature under stirring. The mixture was heated in the microwave for 10 min at100 0C. The mixture was diluted with EtOAc (10 ml) and washed with water and brine ( x3). Organics were dried over sodium sulphate, filtered and the solvent was evaporated to afford the crude product that was purified by silica chromatography to afford the title compound (100 mg, 0.395 mmol). m/z [M+H]+: 228.1 / 230.1. Retention time 0.44 min (LC/MS method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,910656-00-7, 4-Amino-N-methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, 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.65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, molecular weight is 162.19, as common compound, the synthetic route is as follows.

(a) 4-ethyl-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (3.5 g, 21.58 mmol) in THF (100 mL) was added LHMDS (1M in THF) (22.66 mL, 22.66 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction was stirred at this temperature for 1 h. lodomethane (2.418 mL, 22.66 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride (60 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organics were dried over Na2S04, filtered, concentrated, and purified by flash chromatography (0-5% EtOAc in hexanes, 80 g column; re-columned using 0-5% EtOAc in hexanes, 80 g column) to afford 4-ethyl-2-methoxy-6-methylnicotinonitrile (2.01 g, 90% purity) as a white crystalline solid. LC-MS(ES) m/z = 176.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 65515-39-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-79-4, 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. 128071-79-4, name is 4-Bromo-2-fluoro-3-methylpyridine. A new synthetic method of this compound is introduced below.

To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added 4-bromo-2-fluoro-3-methylpyridine (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc’d for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 – 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 – 2.28 (m, 4H), 2.26 – 2.11 (m, 5H), 2.00 – 1.86 (m, 2H), 1.55 – 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-79-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; ZHANG, Liping; HUANG, Audris; SHAN, Weifang; WILLIAMS, David K.; ZHU, Xiao; GUO, Weiwei; (213 pag.)WO2018/209049; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109613-97-0, 2-Bromo-4-methoxypyridin-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, Application In Synthesis of 2-Bromo-4-methoxypyridin-3-amine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Bromo-4-methoxypyridin-3-amine

To a solution of 2-bromo-4-methoxy-pyridin-3-ylamine (540 mg, 2.66 mmol) in pyridine (20 mL) at 0 C is added ethyl chloroformate (0.38 mL, 3.99 mmol). After 30 min, more chloro formate is added (~18 mmol) is added until the reaction goes to completion. The mixture is partitioned between sat. NaHC03 and EtOAc. The two layers are separated, and the aqueous layer is extracted with EtOAc once. The combined organic layers are washed with H20 and brine, dried over MgS04, filterd, and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/MeOH (100/0 to 90/10) as eluant to yield 0.54 g of the product as a white crystalline solid. 1H NMR (CDC13, 300 MHz) 8.18 (d, J= 5.6, 1H), 6.84 (d, J= 5.7, 1H), 6.02 (br s, 1H), 4.23 (q, J = 7.0, 2H), 3.92 (s, 3H), 1.31 (t, J= 7.2, 3H). LC Rt: 1.89 min; LCMS m/z 275 (M+l, 100%).

The synthetic route of 109613-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/78984; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 847729-27-5 ,Some common heterocyclic compound, 847729-27-5, molecular formula is C7H5ClFNO2, 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.

Description 90: methyl 5-fluoro-2-(3-((4-fluoro-2- methylphenyl)amino)azetidin-1-yl)nicotinate (D90)A mixture of methyl 2-chloro-5-fluoronicotinate (D69) (199.85 mg, 1 .054 mmol) and potassium carbonate (291 mg, 2.108 mmol) in tetrahydrofuran (2ml) was stirred under N2 nitrogen 15 min at room temperature. N-(4-fluoro-2- methylphenyl)azetidin-3-amine (D55) (190 mg, 1 .054 mmol) was added and the resulting mixture was stirred 1 day at room temperature. The residue obtained after solvent evaporation was purified by Biotage SNAP-Si column eluting with a mixture cyclohexane/ethyl acetate from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D90)(155 mg)MS: (ES/+) m/z: 334.6 [MH+] C17H17F2N302 requires 333.331 H NMR (400MHz ,CHLOROFORM-d) delta = 8.24 (d, J = 2.9 Hz, 1 H), 7.80 (dd, J = 2.9, 8.3 Hz, 1 H), 6.91 – 6.75 (m, 2 H), 6.32 (dd, J = 4.9, 8.3 Hz, 1 H), 4.50 (dd, J = 7.3, 9.3 Hz, 2 H), 4.40 – 4.27 (m, 1 H), 3.97 – 3.81 (m, 5 H), 3.72 (d, J = 6.4 Hz, 1 H), 2.18 (s, 3 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,847729-27-5, its application will become more common.

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

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. 2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine. A new synthetic method of this compound is introduced below., SDS of cas: 2897-43-0

To a solution of 2,6-dichloro-3-nitro-pyridin-4-amine (2.6 g, 14.4 mmol) from Step A in MeOH (150 mL) was added Raney Nickel catalyst (2 g) and the reaction agitated under a hydrogen atmosphere in a Parr apparatus (35 p.s.i.) for 2 h . The reaction mixture was filtered through a pad of Celite and concentrated to yield the title compound. MS: m/z = 178 (M + 1).

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, 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine.

Reference:
Patent; MERCK & CO., INC.; WO2006/31491; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19235-89-3, 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 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To isopropanol (30.0 mL) was added sodium hydride (0.606 g of 60% dispersion, 15.2 mmol) in small portions over 5 minutes. The resulting gel-like suspension was stirred for an additional 5 minutes at room temperature. 2-Chloro-4-cyanopyridine (2.00 g, 14.4 mmol) was then added in one portion and the resulting solution was heated to reflux. After 1 hour, the reaction mixture was allowed to cool to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried (magnesium sulfate) and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 1.25 g (53%) of product as a colorless oil: 1H NMR (CDCl3) delta 8.27 (d, J=5.2 Hz, 1H), 7.01 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=1.4 Hz, 1H), 5.31 (sept, J=6.2 Hz, 1H), 3.33 (d, J=6.2 Hz, 6H) ppm.

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 19235-89-3, 4-Chloropyridine-2-carbonitrile.

Reference:
Patent; Genzyme Corporation; US2005/176761; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1374655-69-2, 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 1374655-69-2, name is 3-Bromo-4-ethyl-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 9-chloro-l-methyl-7-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-4,5-dihydro-[l,2,4] triazolo[4,3-a]quinoline (80-4; 0.717 g, 0.0020 mol) and 3-bromo-4-ethyl-5-fluoropyridine (0.423 g, 0.0020 mol) in the mixture of 1,4- dioxan (5 mL) and water (5 mL) was added sodium carbonate (0.66 g, 0.0062 mol). Reaction mass was purged with argon for the next 20 min. CatalystPd(dppf)2Cl2.dichloromethane (0.084 g, 0.0001 mol) was added and again purged with argon for 10 min and allowed to stirred at 90 C for 4 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic parts was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography followed by preparative HPLC (analytical conditions; column: ZORBAX XDB (150mm X 4.6mm X 3.5um), mobile phase (A): water, Mobile phase (B): MeOH, flow rate : 1.0 mL/min, gradient T/%B:0/20,6/25,25/75,27/20,30/20) to obtain title compound. 1H NMR (400 MHz, DMSO- d6) delta: 8.55 (s, 1 H), 8.32 (s, 1 H), 7.64 (s, 1 H), 7.55 (s, 1 H), 2.94 (bs, 4 H), 2.65-2.59 (m, 2 H), 2.56 (s, 3 H), 1.09-1.05 (t, J = 7.6 Hz, 3 H). MS (M+l): 343.2.

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 1374655-69-2, 3-Bromo-4-ethyl-5-fluoropyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem