Tag: M.W:100-200

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. 94170-15-7, name is 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde, the common compound, a new synthetic route is introduced below. Safety of 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

Intermediate 2-11 (30 mg, 0.087 mmol) was dissolved in DCM (2 mL)4-Aldehyde-1-methylpyridine-2(1H)-one (14.3 mg, 0.104 mmol), NaBH (OAc) 3 (46.1 mg, 0.218 mmol).Stir at room temperature overnight.TLC monitors the reaction,Add saturated aqueous sodium bicarbonate (5 mL),Extracted with DCM (3 x 10 mL),Combine the organic phase,Wash with water (2 × 5mL),Dry over anhydrous sodium sulfate,filter,concentrate,The crude product was purified by silica gel column chromatography (DCM: MeOH=200:1-20:1)White solid (5.8 mg, yield: 14.5%).

The synthetic route of 94170-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Wang Lin; Yang Xiaoju; Tian Yuwei; (46 pag.)CN108341819; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19346-44-2, 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 19346-44-2 as follows.

[0205] A solution of 2-fluoro-5-methyl-3-nitropyridine (1 g, 6.41 mmol), 4~(2,4~ difluorophenoxy)piperidine hydrochloride (1.919 g, 7.69 mmol) and K2CO3 (2.66 g, 19.22 mmol) in ACN (16.01 mL) was stirred at 80C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The organic layers were combined, dried over Na,2S(>4, and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (I SCO column) eluiing with a gradient of 0-100% EtOAc in heptane to give the title compound as a yellow solid (2.21 g, 99%). NMR (500 MHz, DMSQ-<:) delta ppm 1.66 - 1.73 (m, 2 H), 2.00 (d, J=12.20 Hz, 2 H), 2.25 (s, 3 H), 3.19 - 3.25 (m, 2 H), 3.52 - 3.57 (m, 2 H), 4.58 (dt, J=7,69, 3.72 Hz, 1H), 6,98 - 7.04 (m, 1H), 7.26 - 7.34 (m, 2 H), 8.1 1 (s, 1H), 8.28 -MS m/z [M+H 350.2, These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19346-44-2, its application will become more common. Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1443-42-1, 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 1443-42-1, name is (4-Methylpyridin-3-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows.

In a sealed tube, a mixture of intermediate 5 (0.5 g, 1.01 mmol), (4-Methylpyridin- 3-yl)methylamine (0.108 mL, 1.21 mmol) and cesium carbonate (0.66 g, 2.02 mmol) in tert-amyl alcohol (5mL) was degazed with N2. 2-Dicyclohexyphosphino-2′,6′- diisopropoxy-l,l ‘-biphenyl (23.544 mg, 0.0505 mmol) and BrettPhos Precatalyst First Gen (40.305 mg, 0.0505 mmol) were added, the reaction mixture was purged with N2and heated at 100C for 18 h. Water and Ethyl acetate were added. The aqueous layer was extracted and the organic layer was separated, dried over MgS04, filtered and concentrated. This crude (578 mg) was purified by silica gel chromatography (25g of SiOH, 15muiotaeta, gradient from 100% DCM to 90/10/0.1 DCM/MeOH/NH4OH). The fractions containing the product were collected and evaporated until dryness to afford 405 mg (74%) of intermediate 6 which was used in the next step without any further purification.

According to the analysis of related databases, 1443-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20970-75-6, Adding some certain compound to certain chemical reactions, such as: 20970-75-6, name is 2-Cyano-3-methylpyridine,molecular formula is C7H6N2, 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 20970-75-6.

General procedure: General Procedure for the Preparation of 7-Aza-5,6-dihydro-5-oxo-11H-indeno[1,2-c]isoquinolines 12-14 [0111] 3-Methylpicolonitrile (10, 3.0-4.0 g, 25.4-33.9 mmol, 1 equiv), NBS (6.78-9.04 g, 38.1-50.8 mmol, 1.5 equiv), and AIBN (0.42-0.56 g, 2.5-3.4 mmol, 0.1 equiv) were diluted with 1,2-dichloroethane (80-100 mL), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was concentrated to half its original volume, filtered, and the filtrate was concentrated to dryness to provide crude 11. Compound 11 was diluted with acetonitrile (100-125 mL). The appropriate homophthalic anhydride (5, 6, or 7, 6.8-12.4 g, 41.9-55.9 mmol, 1.65 equiv) was added, followed by triethylamine (18-24 mL, 127.0-169.5 mmol, 5 equiv), and the solution was heated at reflux for 10 h. The solution was allowed to cool to room temperature, and the precipitate was filtered and washed with hot acetonitrile (2×35 mL) to provide the described compound.

According to the analysis of related databases, 20970-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CUSHMAN, Mark S.; KISELEV, Evgeny A.; MORRELL, Andrew E.; US2014/18360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 201937-23-7 ,Some common heterocyclic compound, 201937-23-7, molecular formula is C6H7Cl2N3, 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.

Compound 88 (1.08 g, 3.14 mmol), 6-chloropyridine-3-carboxirnidamide hydrochloride (900 mg, 4.69 mmol) and K2CO3 (1.30 g, 9.42 mmol) in EtOH (15 mL) were heated in a Biotage microwave synthesizer at 120 C for 3 h. After the reaction was cooled to room temperature, EtOAc was added. The mixture was washed with water. The organic extract was dried with Na2S04and concentrated. The crude product was dissolved in CH2CI2 (31 mL) and treated with DDQ (713 mg, 3.14 mmol). After the reaction was stirred at room temperature for 1 h, aq. sat. NaHCCb was added. The mixture was stirred at room temperature for 10 min; filtered through a pad of Celite; and eluted with CH2CI2. The organic phase of the filtrate was separated. The aqueous phase was extracted with CH2CI2. The combined organic extract was dried with Na2S04 and filtered and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 0% to 5% EtOAc in CH2CI2) to give compound 363 (902 g, 60% yield) as a white foamy solid, m/z = 480 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; BENDER, Christopher, F.; VISNICK, Melean; HOTEMA, Martha, R.; SHELDON, Zachary, S.; LEE, Chitase; CAPRATHE, Bradley, William; BOLTON, Gary; KORNBERG, Brian; (497 pag.)WO2018/111315; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75893-75-3, 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. 75893-75-3, name is 6-Cyclopropylnicotinic acid. A new synthetic method of this compound is introduced below.

Example 56 6-Cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (56) In a 10-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, [2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methanamine (100 mg, 0.31 mmol, 1.00 equiv) and 6-cyclopropylpyridine-3-carboxylic acid (60.7 mg, 0.37 mmol, 1.20 equiv) were dissolved in N,N-dimethylformamide (2 mL), to which were added HATU (176.9 mg, 0.47 mmol, 1.50 equiv) and DIEA (120.3 mg, 0.93 mmol, 3.00 equiv) in sequence at room temperature. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by the addition of 5 mL water and the mixture was extracted with dichloromethane (3*10 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC using the following conditions: column, X Bridge C18, 19*150 mm, 5 um; mobile phase, acetonitrile in water (with 0.05% TFA), 30% to 70% gradient in 10 min; detector, UV, 254 nm. 6-cyclopropyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-3-carboxamide (20 mg, 13%) was obtained as white solid. HPLC: 97.7% purity. MS: m/z=468.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 6 13.39 (br s, 1H), 9.20-9.17 (m, 1H), 8.91 (d, J=2.0 Hz, 1H), 8.44 (s, 1H), 8.29-8.20 (m, 2H), 8.14-8.11 (m, 3H), 7.56-7.52 (m, 2H), 7.42 (d, J=8.0 Hz, 1H), 4.60 (s, 2H), 3.94 (s, 3H), 2.33-2.15 (m, 1H), 1.05-1.01 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75893-75-3, 6-Cyclopropylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109613-90-3, 2-Chloro-3-fluoro-4-nitropyridine, 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-Chloro-3-fluoro-4-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-3-fluoro-4-nitropyridine

A solution of 2-aminoethanol (0.67 mL; 11 mmol) cooled to 0 C was treated with 2-chloro-3-fluoro-4- nitropyridine (2.00 g; 11 mmol) and stirred for 0.5 h. A solid was formed, which was then purified by column chromatography (silica gel; PE : EA; 1 :1 to 0:1 ; v/v) to afford 2-[(2-chloro-4-nitro-3- pyridyl)amino]ethanol (1.68 g) as an orange solid. ‘H-NMR (400 MHz, CDC13) delta ppm: 7.85 (d, J= 5.6 Hz, 1H), 7.68 (d, J= 5.6 Hz, 1H), 3.89 – 3.85 (m, 2H), 3.56 – 3.52 (m, 2H).

The synthetic route of 109613-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; RICHALET, Florian; WEILER, Sven; EL SHEMERLY, Mahmoud; LANE, Heidi; (131 pag.)WO2019/72978; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19235-89-3, 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 19235-89-3 as follows.

Step 3. Preparation of 4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)picolinonitrile To the reaction mixture of 2-(cyclohexylmethylamino)benzo[d]thiazol-6-ol (18 mg, 0.068 mmol) in 0.4 ml of NMP was added Cesium Carbonate (56 mg, 0.171 mmol) and stirred at RT for 1-3 minutes. To this mixture was added 4-chloropicolinonitrile (19 mg, 0.136 mmol). The reaction mixture was stirred at 60 C. for 5 hours or until done by LC. The crude reaction mixture was filtered, purified on prep HPLC and lyophilized to give 4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)picolinonitrile as TFA salt (9.8 mg). ES/MS m/z 365.1 (MH+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19235-89-3, its application will become more common.

Reference:
Patent; Novartis AG; US2008/45528; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16744-81-3, Adding some certain compound to certain chemical reactions, such as: 16744-81-3, name is 4-Methoxypicolinaldehyde,molecular formula is C7H7NO2, 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 16744-81-3.

General procedure: A mixture of 6-(3 -hydroxypropoxy)-4-(6-(piperazin- 1 -yl)pyridin-3 -yl)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile hydrochloride (Intermediate P51; 12.1 mg, 0.0292mmol), 5-chloropicolinaldehyde (8.26 mg, 0.0583 mmol) and NaBH(AcO)3 (18.5 mg, 0.0875mmol) in DCE (583 tL) was stirred for 1 day at ambient temperature. The mixture was purified directly by C18 reverse phase (5-95percent ACN/ water with 0.1percent TFA as the gradient eluent) to afford the title compound (17.1 mg, 95percent yield). MS (apci) m/z = 504.2 (M+H).

According to the analysis of related databases, 16744-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189230-41-9, 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. 189230-41-9, name is 2-Bromopyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

A mixture of intermediate 22 (1.8 g, 9.57 mmol) and 4-fluoro-benzoic acid (1.34 g, 9.57 mmol) in polyphosphoric acid (25 g) was stirred and heated at 180 0C for Ih. The r.m. was cooled to r.t, and water was added. The resulting sol. was neutralized with K2CO3, and the resulting precipitate was filtered off and washed with water. Yield: 1 g of crude intermediate 23, which was used as such in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189230-41-9, 2-Bromopyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; MACDONALD, Gregor, James; BISCHOFF, Francois, Paul; WU, Tongfei; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; ZAJA, Mirko; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; DE CLEYN, Michel, Anna, Jozef; OEHLRICH, Daniel; WO2010/89292; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem