Month: April 2022

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 1227002-03-0, name is Methyl 2-amino-5-chloroisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H7ClN2O2

To a solution of methyl 2-amino-5-chloroisonicotinate (4.75 g, 25.5 mmol) in DMF (40 mL) was added 4-(dimethylamino)pyridine (0.466 g, 3.82 mmol), triethylamine (10.62 mL, 76 mmol), and di-tert-butyl dicarbonate (16.67 g, 76 mmol). The reaction was stirred at room temperature for 3 d. The reaction was quenched with water (40 mL). The aqueous layer was extracted with EtOAc (100 mL, three times), and the combined organic layers were washed with water, brine, dried (MgS04) and concentrated. The residue was purified by flash chromatography (80 g silica gel column, gradient elution from hexanes to 15% EtOAc/hexanes) to provide bis-Boc aminopyridine (6.36 g, 16.44 mmol) as a white powder.

With the rapid development of chemical substances, we look forward to future research findings about 1227002-03-0.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, 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, SDS of cas: 944900-06-5, blongs to pyridine-derivatives compound. SDS of cas: 944900-06-5

General procedure: A mixture of 2-chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 13 (19.0 g, 90.8 mmol), Ti(OEt)4 (41.4 g. 182 mmol), and (S)-(-)-tert-butylsulfinamide (11.2 g. 92.6 mmol) in THF (200 mL) was stirred at reflux for 5 h. The cooled reaction mixture was concentrated, and dissolved in ethylacetate (500 mL). The resulting suspension was filtered through a Celite pad, and the filtrate was concentrated and purified by column chromatography (hexane/ EtOAc = 4 : 1) to provide the imine (28.9 g) as a light yellow solid. A mixture of the imine (28.9 g, 92.5 mmol), allyl bromide (55.9 g, 0.46 mmol), and indium (42.5 g, 0.37 mmol) was vigorously stirred in sat. NaBraq at room temperature overnight. After addition of sat. NaHCO3 aq (500 mL), the reaction mixture was extracted with ethylacetate (250 mL x 3). The organic layers were filtered through a Celite pad, and dried (Na2SO4), concentrated and purified by column chromatography (hexane/ EtOAc = 1 : 4 with 5 % of Et3N) to provide 17 as a white solid (26.0 g, 77 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Youko; Yoshida, Kazuhiro; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 750 – 755;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184416-84-0, 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 184416-84-0 as follows.

Thionyl chloride (92 mul, 1.25 mmol) is added to a mixture of 2,3-dichloro-pyridine-4-carboxylic acid (200 mg, 1.04 mmol), DCM (2 ml) and DMF (20 mul). The mixture is heated to 100 C. for 10 minutes in a microwave. The mixture is concentrated in vacuo. DCM (2.5 ml) and 1,2-dimethylhydrazine dihydrochloride (207 mg, 1.55 mmol) is added before DIPEA (1.35 ml, 7.77 mmol) in DCM (2.5 ml) is added dropwise at RT. Stirring is continued for 1 hour. The mixture is diluted with DCM and extracted with water. The combined organic layers are dried over Na2SO4 and concentrated in vacuo. NMP (1 ml) and triethylamine (200 mul, 1.5 mmol) is added and the mixture heated to 190 C. for 25 minutes in a microwave. At RT water is added (500 mul) and the product purified by RP HPLC. Yield: 50 mg (24%). HPLC-MS: M+H=198; tR=0.44 min (METHOD-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,184416-84-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; US2015/57286; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89694-10-0, Adding some certain compound to certain chemical reactions, such as: 89694-10-0, name is 2-Methoxy-3-methyl-5-nitropyridine,molecular formula is C7H8N2O3, 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 89694-10-0.

2-methoxy-3-methyl-5-nitropyridine (4.30 g; 25.57 mmol) and tert-butyl chioroacetate (4.50 mL; 31.37 mmol) in THF (60 mL) was stirred and cooled at -20C. Then potassium tert-butoxide (6.80 g; 60.60 mmol) was added portionwise to this mixture(temperature keep below -14C). After complete addition, this reaction was stirred at rt for 1 h. Water and an aqueous solution of HC1 3N were added and this mixture was extracted twice with EtOAc. The organic layer was decanted and the solvent was evaporated until dryness to give 7.35 g of intermediate 480 (100% yield).

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. 89694-10-0, 2-Methoxy-3-methyl-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); 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. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine. A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-2-chloro-4-methylpyridine

Example 193; Synthesis of 3-bromo-4-methylpyridin-2(1H)-one; To a resealable pressure vessel charged with 3-bromo-2-chloro-4-picoline (1.200 g, 5.81 mmol) was added formic acid (13.1 ml, 348 mmol) and water (4.00 ml, 222 mmol). The tube was sealed and the solution heated to 1200C. After 72 hrs, the solution was cooled to RT and concentrated in vacuo. The residue was purified by reverse phase chromatography (neutral) to afford 3-bromo-4- methylpyridin-2(1H)-one as a white solid. M+H+ = 188.0.

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, 55404-31-4, 3-Bromo-2-chloro-4-methylpyridine.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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. Product Details of 64951-08-2

To a solution of imidazo[l,2-a]pyridine-2-carboxylic acid (262 mg, 1.62 mmol) in N,N-dimethylformamide (5 mL) was added l-[bis(dimethylamino)methylene]-lH-l,2,3- triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU, 616 mg, 1.62 mmol), ethyldiisopropylamine (697mg, 5.40 mmol). The resulting mixture was stirred at room (0804) temperature for 30 min. Ethyl 2-((2S,4tf)-4-((((9H-fluoren-9-yl) (0805) methoxy)carbonyl)amino)pyrrolidin-2-yl)thiazole-4-carboxylate (500 mg, 1.08 mmol) was added. The mixture was stirred at room temperature for 12 h. The mixture was concentrated, dissolved in ethyl acetate, washed with 1 N lithium chloride. The organic layer was concentrated to give ethyl 2-((2S,4 ?)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-l-(imidazo[l,2- a]pyridine-2-carbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate as a brown solid. MS(ESI) m/z 608.2 [M + H]+.

With the rapid development of chemical substances, we look forward to future research findings about 64951-08-2.

Reference:
Patent; DYAX CORP.; TRAVINS, Jeremy; MILLER, Thomas; PAPAIOANNOU, Nikolaos; (199 pag.)WO2019/28362; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57883-25-7, 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 57883-25-7, name is 3-Bromo-2-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1 1.0034-{2-[(2-ethoxypyridin-3-yl)amino][1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl}-N- 2,2,2-trifluoroethyl)benzamide4-(2-Amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-N-(2,2,2-trifluoroethyl)benzamide Int9.2 (100 mg), 3-bromo-2-ethoxypyridine Int22.1 (72 mg), chloro(2-dicyclo- hexylphosphino-2′,4′,6′-tri-i-propyl-1 , 1 ‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) (22 mg), X-Phos (14 mg), and sodium tert-butoxide (52.3 mg) were pre-mixed, and degassed toluene (2.2 mL) was added. The mixture was heated for 6h to 130 C. Subsequently, DCM was added, and the mixture was washed with satd. aqueous Na2C03 solution. The organic layer was dried over Na2S04, and the solvent was evaporated. The crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate / ethanol gradient 50: 1 to 20: 1 ) to yield 86 mg (63%) of the title compound.1 H-NMR (400MHz, DMSO-d6): delta [ppm]= 1 .41 (t, 3H), 4.08 – 4.18 (m, 2H), 4.42 (q, 2H), 7.01 (dd, 1 H), 7.70 – 7.75 (m, 2H), 7.95 – 8.06 (m, 5H), 8.35 (s, 1 H), 8.53 (dd, 1 H), 9.18 (t, 1 H), 9.30 (s, 1 H).

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 57883-25-7, 3-Bromo-2-ethoxypyridine.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philipp; MARQUARDT, Tobias; WEGSCHEIDT-GERLACH, Christof; SIEMEISTER, Gerhard; PRECHTL, Stefan; WENGNER, Antje; BOeMER, Ulf; WO2011/64328; (2011); 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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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. Recommanded Product: Imidazo[1,2-a]pyridine-2-carboxylic acid

Step (e) N-{4-[6-fluoro-2,4-dioxo-l-[3-(pyridin-3-ylethynyl)phenyl]-l,4- dihydropyrido[2,3-d]pyrimidin-3(2H)-yl]cyclohexyl}imidazo[l,2-a]pyridine-2- carboxamideTo a mixture of imidazo[l,2-a]pyridine-2-carboxylic acid (1 lOmg, 0.68mmol), HATU (250mg, 0.66mmol) and 3-(4-aminocyclohexyl)-6-fluoro-l-[3-(pyridin- 3ylethynyl)phenyl]-pyrido[2,3-d]pyrimidine-2,4(lH,3H)-dione dihydrochloride (230mg, 0.44mmol) in Chloroform was added ethyl-di-isopropylamine (0.38ml, 2.2mmol) over a period of 20 seconds. Stirring was continued at ambient temperature for 15 hours. Water was added to the clear solution and the mixture was concentrated under reduced pressure using a rotary evaporator. The obtained solid was filtered and dissolved in acetonitrile. Purification on preparative HPLC resulted in the title compounds as an off white solid (45mg, 17%). 1U NMR (DMSO-ck): delta 8.75 (IH, s); 8.55 – 8.62 (3H, m); 8.38 (IH, s); 8.34 (IH, dd); 7.98 (IH, ddd); 7.57 – 7.74 (4H, m); 7.44 – 7.52 (2H, m); 7.33 (IH, brdd); 6.98 (IH, brdd); 4.87 (IH, bt); 4.18 (IH, bs); 2.54 – 2.69 (2H, brm); 2.00 (2H, brd); 1.59 – 1.79 (4H, m). APCI-MS m/z: 599 [MH+].

With the rapid development of chemical substances, we look forward to future research findings about 64951-08-2.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 107867-51-6, 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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine. A new synthetic method of this compound is introduced below.

To a vial were added l-(4-(methoxycarbonyl)phenyl)cyclobutanecarboxylic acid (25 mg, 0.11 mmol), 5-(trifluoromethyl)pyridine-2,3-diamine (28.4 mg, 0.160 mmol), HATU (60.9 mg, 0.160 mmol), DMF (800 mu) and DIEA (70 mu, 0.40 mmol). The mixture was heated at 130 C for 20 h. The mixture was filtered and purified by reversed phase HPLC, eluting with ACN/water (0.1%TFA) to afford the title compound as the TFA salt. MS (EI) m/z 376 [M+H] .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,107867-51-6, 5-(Trifluoromethyl)pyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5, 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.23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine, molecular formula is C6H5BrN2O2, molecular weight is 217.02, as common compound, the synthetic route is as follows.

Step 1 [0610] A suspension of 2-bromo-4-methyl-5-nitropyridine (XIV) (200 g, 921 mmol, 1.00 eq) and NH4C1 (240 g, 4.49 mol, 4.87 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 50C. To this mixture was added Fe ( 120 g, 2.15 mol, 2.33 eq) and HC1 (10.2 g, 279 mmol, 0.30 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-4-methylpyridin-3 -amine (XV) as brown solid (167.9 g, 898 mmol, 97.4% yield) which was used for the next step without any purification. l NMR (CDC , 400 MHz) delta ppm 2.15 (s, 3H), 3.44 (br s, 2H), 7.14 (s, 1H), 7.78 (s, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

The chemical industry reduces the impact on the environment during synthesis 23056-47-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (261 pag.)WO2017/23984; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem