Month: April 2022

Application of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile. A new synthetic method of this compound is introduced below.

A) 6-methoxynicotinonitrile To a solution of 6-chloronicotinonitrile (10.0 g) in methanol (100 mL) was added sodium methoxide (7.80 g). The reaction mixture was heated at reflux overnight, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (8.8 g). 1H NMR (400 MHz, DMSO-d6) delta 4.00 (3H, s), 6.83 (1H, dd, J= 8.8, 0.8 Hz), 7.78 (1H, dd, J= 8.6, 2.4 Hz), 8.50 (1H, d, J = 1.4 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-28-7, 6-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 145255-19-2, 5-Aminopyridine-2-carboxamide, 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: 145255-19-2, blongs to pyridine-derivatives compound. Recommanded Product: 145255-19-2

Example 351 5-((4-((3S)-3-cyano-3-isopropyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)pyridine-2-carboxamide To a solution of (3S)-1-(2-chloropyrimidin-4-yl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile (200 mg) obtained in Step A of Example 9, 5-aminopyridine-2-carboxamide (120 mg) obtained in Step A of Example 350, cesium carbonate (490 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (71 mg) in tetrahydrofuran (5.0 mL) was added tris(dibenzylideneacetone)dipalladium(0) (69 mg), and the mixture was stirred overnight at 80C under argon atmosphere. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized (diisopropyl ether/ethanol) to give the title compound (54 mg). MS(ESI+): [M+H]+ 366.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145255-19-2, 5-Aminopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TSUKAMOTO, Tetsuya; OHBA, Yusuke; YUKAWA, Takafumi; NAGAMIYA, Hiroyuki; KAMEI, Taku; TOKUNAGA, Norihito; SAITOH, Morihisa; OKABE, Atsutoshi; EP2832734; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 26956-43-4, 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. 26956-43-4, name is Furo[3,2-c]pyridin-4(5H)-one, molecular formula is C7H5NO2, 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.

To a mixture of furo [3 2-c] pyridin-4 (5H) -one (5 g 37.0 mmol) in MeCN (50 mL) was added a solution of NBS (8.56 g 48.1 mmol) in MeCN at 0 over 10 min. The resulting suspension was stirred at 0 for 1 h and warmed to rt for 10 min. Water (250 mL) and saturated aqueous NaHCO3(10 mL) ware added to the mixture. Off-white solids ware collected by filtration and dried to afford 7-bromofuro [3 2-c] pyridin-4 (5H) -one (1.5 g 5.96 mmol 16.10 yield) 1HNMR(400 MHz CD3OD) delta 7.82 (d J 2.0 Hz 1H) 7.51 (s 1H) 7.05 (d J 2.4 Hz 1H) ES-LCMS m/z 214.0 215.9 (M+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 26956-43-4, Furo[3,2-c]pyridin-4(5H)-one.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79055-59-7, 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. 79055-59-7, name is 2-Bromo-6-methylpyridin-4-amine, molecular formula is C6H7BrN2, 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.

General procedure: 3-Amino-2-bromo-6-methylpyridine(7a) or4-amino-2-bromo-6-methylpyridine(7b) (25.20 g, 134.73 mmol) wasadded to a mixture of water (78.1 mL) and conc. HCl (12.8 mL, 350.30 mmol), andthen the mixture was cooled to 0 oC. To it, sodium nitrite (18.6 g,269.46 mmol) was added portionwise with stirring over a period of 20 min whilekeeping the reaction temperature between -5 oCand 0 oC. After 10 min, 65% hexafluorophosphoric acidsolution (43.26 g, 296.41 mmol) was added dropwise with cooling, atwhich point a lot of precipitates were formed. The precipitates were collectedby filteration using a glass filter funnel, washed with cold water (2 × 50 mL) and diethyl ether (100 mL), and then dried in the air for 48 h.The solid was slowly heated to 100 oC (very exothermic), and a darkred oily material was formed after 10 min. The oil was basified with dilutedNaOH solution to pH~10 and extracted with CH2Cl2 (2 × 150 mL). The combined organic layer was dried over anhydrous Na2SO4,filtered, and evaporated to dryness under reduced pressure. The residue waspurified by MPLC on neutral alumina using hexane/EtOAc (10:1) as eluent to affordthe titled compounds.

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 79055-59-7, 2-Bromo-6-methylpyridin-4-amine.

Reference:
Article; Krishnaiah, Maddeboina; Jin, Cheng Hua; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5228 – 5231;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Fluoro-3-(hydroxymethyl)pyridine

To a solution of (2-fluoropyridin-3-yl)methanol (500 mg 3.93 mmol) in DCM (15 mL) at 0 C. was added phosphorus tribromide (2.13 g, 7.87 mmol). The reaction mixture was stirred at room temperature for 16 hours. Water (10 mL) was added and the mixture was extracted with ethyl acetate (30 mL*3). The combined organic layers were washed with brine (20 mL), dried over Na2SO4 and concentrated to give 5-((tert-butyldimethylsilyl)oxy)pentan-1-ol.

With the rapid development of chemical substances, we look forward to future research findings about 131747-55-2.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; US2019/185489; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 39891-09-3 ,Some common heterocyclic compound, 39891-09-3, 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.

(6-Chloro-pyridin-3-yl)-acetic acid ethyl ester To a solution of EtOH (27 mL), concentrated H2SO4 (10 mL) was added dropwise and 2-chloropyridine-5-acetonitrile (2.00 g, 13.1 mmol) was added portionwise. The solution was stirred at 100C for three hours. The mixture was added dropwise to a solution of NaHCO3 (30.00 g) in H2O (100 mL) and it was extracted twice with DCM. The organic layer were collected, dried and evaporated to give the title compound (2.60 g, quant.) C9H10ClNO2 Mass (calculated) [199]; (found) [M+H]+ = 200.

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. 39891-09-3, 2-Chloropyridine-5-acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Siena Biotech S.p.A.; Caramelli, Chiara; Federico, Cesare; Gabellieri, Emanuele; Magnani, Matteo; Micco, Iolanda; EP2878339; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.89694-10-0, name is 2-Methoxy-3-methyl-5-nitropyridine, molecular formula is C7H8N2O3, molecular weight is 168.15, as common compound, the synthetic route is as follows.Safety of 2-Methoxy-3-methyl-5-nitropyridine

Dimethyl sulfoxide (35 mL) was added to a dry round-bottomed flask containing NaH (1.82 g, 45.5 mmol, 60% in mineral oil). The resulting suspension was heated at 70 C. for 35 min during which time the suspension became a solution. The reaction mixture was cooled to room temperature, trimethylsulfoxonium iodide (10.0 g, 45.5 mmol) was added, and the mixture was stirred at room temperature for 30 min. 2-Methoxy-3-methyl-5-nitropyridine (4.50 g, 26.80 mmol) was added and the resulting dark red solution was stirred at room temperature for 30 min, at which time TLC showed complete consumption of starting material. The reaction mixture was transferred to a separatory funnel containing water (30 mL), and the aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by MPLC (silica gel, 20% ethyl acetate in hexanes) to afford 2-methoxy-3,6-dimethyl-5-nitropyridine (2.00 g, 41% yield) as a colorless solid identical to that prepared by the previous method: mp 85.5-86.2 C.; 1H NMR (400 MHz, CDCl3) delta 8.08 (s, 1H), 4.02 (s, 3H), 2.77 (s, 3H), 2.20 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89694-10-0, 2-Methoxy-3-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/29684; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58539-65-4, 2-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, 58539-65-4, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methylnicotinamide

Step 2 Preparation of 3-cyano-2-methylpyridine: To a suspension of 2-methylnicotinamide from step 1 (11.1 g, 0.081 mol) in triethylamine (24.8 g, 0.243 mol) and 400 mL of methylene chloride was added trifluoroacetic anhydride (21.0 g, 0.100 mol) rapidly at 0 C. The reaction was complete after a few minutes at this temperature. Water was added and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/hexane, 1:1) to give 7.2 g of 3-cyano-2methylpyridine as a pale yellow solid (75%): mp(DSC) 56-58 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-65-4, its application will become more common.

Reference:
Patent; GD Searle & Co; US5616601; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 914358-72-8, 5-Bromo-3-chloro-2-methylpyridine, 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: C6H5BrClN, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5BrClN

[00443] To a solution of Example 75a (150 mg, 0.33 mmol), Example 75b (75 mg, 0.36 mmol) in 1,4- dioxane/H20 (4 mL/1 mL) were added Pd(dppf)Cl2 (24 mg, 0.033 mmol) and Na2C03 (70 mg, 0.66 mmol). The mixture was degassed by nitrogen for three times and heated at 95C for 2 h. The reaction mixture was filtered, washed with EtOAc and concentrated. The residue was purified by prep-TLC (DCM/MeOH = 15/1) to give the desired product Example 75 (49.0 mg, yield 33%) as a gray solid.LCMS [M/2+l]+ = 231.0. NMR (400 MHz, DMSO- 6) 5 11.18 (s, 1H), 8.73 (d, J= 2.1Hz, 1H), 8.68 (s, 1H), 8.24 (d, J= 2.6 Hz, 1H), 8.18 (d, J= 2.1Hz, 1H), 8.04 (d, J= 7.9 Hz, 1H), 7.98 (dd, J= 8.7, 2.6 Hz, 1H), 7.86 (dd, J= 13.0, 7.8 Hz, 2H), 7.39 (d, J= 8.6 Hz, 1H), 4.36 (t, J= 5.0 Hz, 2H), 4.30-4.20 (m, 2H), 2.56 (s, 3H), 2.43 (br, 2H), 1.96 (d, J= 7.1Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,914358-72-8, 5-Bromo-3-chloro-2-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 97004-04-1, 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.97004-04-1, name is (6-Chloropyridin-3-yl)methanamine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

EXAMPLE 29 To a mixture of O-methyl-N-nitroisourea (1.25 g, 10.53 mmol), water (20 ml) and concentrated hydrochloric acid (0.85 ml, 10.03 mmol) was added 5-(aminomethyl)-2-chloropyridine (1.43 g, 10.03 mmol) dropwise over 5 minutes at room temperature with stirring. The reaction mixture was neutralized with 40% aqueous sodium hydroxide solution and adjusted to pH 7.2. After 17 hours of stirring at room temperature, the resulting crystals were collected. The crystals were washed with water and dried. As a result, 1.16 g (47.3% yield) of O-methyl-N-(6-chloro-3-pyridylmethyl)-N’-nitroisourea was obtained as white crystals. M.p. 112-113 C. 1 H-NMR (CDCl3) delta: 3.98 (3H, s), 4.57 (2H, d, J=6.0 Hz), 7.38 (1H, d, J=8.2 Hz), 7.63 (1H, dd, J=8.2 Hz, 2.4 Hz), 8.36 (1H, d, J=2.4 Hz), 9.43 (1H, br). IR (nujol): 3250, 1590, 1520, 1390, 1240, 1210 (cm-1).

The chemical industry reduces the impact on the environment during synthesis 97004-04-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6008363; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem