Category: pyridine-derivatives

Reference of 1796-84-5, 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 1796-84-5 as follows.

4-Ethoxy-3-nitropyridine, hydrochloride (14.5 g, 70.8 mmol) in ethyl acetate was washed twice with 1 N NaHCO3. The organic layer was dried over MgS04, filtered and the solvent evaporated under reduced pressure to give 11.8 g of a light tan solid. The free-amine (11.8 g, 69.9 mmol) and cyclopropanemethylamine (5.00 g, 70.3 mmol) in EtOH were heated at 80 C in a sealed tube for 12 h. After allowing to warm to RT, the solvent was removed under reduced pressure to give a yellow oil. Flash chromatography (silica gel, hexanes then hexanes/Et2O (1: 1: 1) then Et2O/CH2CI2 (1: 1) then CH2CI2) gave 13.1 g of the desired material. MS (ES) m/z 194.2 [M+H] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1796-84-5, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1095823-39-4, 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 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial was charged with compound G.4 (191.8 mg, 0.65 mmol), CH2Cl2 (3.0 mL), a 2.0 M solution of oxalyl chloride in CH2Cl2 (390 muL), and DMF (10.0 muL, 0.129 mmol). The reaction mixture was stirred for 15 minutes at room temperature, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound G.5 (129 mg, 0.65 mmol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography (SiO2, 0-30% EtOAc/CH2Cl2) to give compound G.6 in 49% yield. LCMS: m/z = All [M+l].

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 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; CHUAQUI, Claudio; COSSROW, Jennifer; DOWLING, James; GUAN, Bing; HOEMANN, Michael; ISHCHENKO, Alexey; JONES, John, Howard; KABIGTING, Lori; KUMARAVEL, Gnanasambandam; PENG, Hairuo; POWELL, Noel; RAIMUNDO, Brian; TANAKA, Hiroko; VAN VLOTEN, Kurt; VESSELS, Jeffrey; XIN, Zhili; WO2010/78408; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 108724-09-0, name is 7-Bromothiazolo[4,5-c]pyridine, the common compound, a new synthetic route is introduced below. name: 7-Bromothiazolo[4,5-c]pyridine

The mixture of 6-(2-amino-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2- yl)pyridin-3-yl)-3,4-dihydroisoquinolin-1 (2H)-one (2-24, 68 mg, 0.186 mmol), 7- bromothiazolo[4,5-cjpyridine (2-124, 40 mg, 0.186 mmol), K3P04 (79 mg, 0.372mmo1), Pd(PPh3)2C12(13 mg, 0.0018 mmol)in THF(2 mL), and H20 (0.1 mL)was stirred at 65C for 16 h under N2 atmosphere. Upon reaction completion, the resulting mixture was filtered and concentrated under reduced pressure. The resulting residue was purified by prep-HPLC (C18 column, CH3CN/H20, containing 0.05% NH4HCO3) to get title compound 1-56 (white solid, 7 mg, 10 %). LCMS: 374 [M + Hj HPLC: 100% (254 nm); ?H NMR (400 MHz, DMSO-d6) oe 9.58 (s, 1H), 9.31 (s, 1H), 8.73 (s, 1H), 8.43 (d, J= 2.4 Hz, 1H), 7.97 (s, 1H), 7.94 (d, J 7.8 Hz, 1H), 7.79 (d, J 2.3 Hz, 1H), 7.52 (d, J= 9.4 Hz, 2H), 6.22 (s, 2H), 3.42 (s, 2H), 2.97 (t, J 6.4 Hz, 2H).

The synthetic route of 108724-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; FONDAZIONE CENTRO SAN RAFFAELE; GRAY, Nathanael S.; BUHRLAGE, Sara; ANDERSON, Kenneth; COTTINI, Francesca; TONON, Giovanni; (288 pag.)WO2016/161145; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 193274-02-1 , The common heterocyclic compound, 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate, molecular formula is C19H25N3O3, 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.

Step D. 3a(R)-Benzyl-2-methyl-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one (L)-tartrate To a 2 liter, round bottom flask, equipped with a mechanical stirrer, addition funnel, and a thermocouple was added, sequentially, 3a-(R,S)-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydro-pyrazolo[4,3-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared according to Step C, 51.5 g, 0.15 moles, 1.0 equivalents) and methylene chloride (515 ml, 10 volumes). The mixture was agitated to form a solution which was then cooled to an internal temperature of 0 C.-5 C. To the cooled mixture was added trifluoroacetic acid (TFA, 130 ml, 192 g, 1.68 moles, 11.2 eq., 2.5 volumes). The TFA was added via the addition funnel over 15 minutes while maintaining an internal temperature of 0 C.-5 C. The reaction mixture was warmed to about 20 C. over 3 hours and then the reaction mixture was cooled to 10 C.-15 C. To the cooled reaction mixture was added sodium carbonate (92 g, 0.868 moles) in water (920 mL) over 20 minutes. The pH was 7.5. The reaction mixture was transferred to a 2 liter separatory funnel and allowed to settle. The organic portion was decanted and the aqueous portion was extracted with methylene chloride (130 ml, 2.5 volumes). The combined organic portions were transferred back to the 2 liter reactor and to it was added L-tartaric acid (24.77 g, 0.165 moles, 1.1 equivalents) dissolved in acetone (354 ml, about 7 volumes) and water (44 mL, about 1 volume). The reaction mixture was agitated and heated at about 38 C. overnight. The resultant slurry was cooled to 0 C.-5 C., granulated for 1 hour, then filtered. The solids were washed with 100 ml of cold acetone and then dried in vacuo at 40 C.-50 C. for 16 hours to afford 51.86 g (87.9% yield) of the title compound of Step D.

The synthetic route of 193274-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Busch, Frank R; Chiu, Charles K; Meltz, Clifford N; Post, Ronald J; Rose, Peter R; US2002/2283; (2002); 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. 832715-99-8, name is 6-(tert-Butyl)nicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-(tert-Butyl)nicotinic acid

To a solution of Intermediate 3 (250 mg, 0.83 mmol), tert-butylcarboxylic acid(89 mg, 0.88 mmol), 6-(tert-butyl)pyridine-3-carboxylic acid (158 mg, 0.88 mmol), EDC (270 mg, 1.25 mmol) and HOBT (150 mg, 0.83 mmol) in DCM (5 mL) was added DIPEA (250 muL, 1.66 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction was quenched with water (10 mL). The organic layer was separated, dried (MgSO4), concentrated in vacuo and chromatographed (SiO2, 20: 1 EtOAc/MeOH), yielding the title compound (140 mg, 34%) as a white solid after freeze-drying with 1 : 1 MeCN-water. deltaH (d6-DMSO) 8.30 (s, IH), 7.61 (s, IH), 7.41-7.37 (m, 2H), 7.32 (d, J 8.1 Hz, IH), 7.21 (dd, J8.4, 1.4 Hz, IH), 7.07 (s, IH), 4.30-4.18 (m, IH), 3.93-3.90 (m, IH), 3.82 (d, J 11.6 Hz, IH), 3.78-3.75 (m, 4H), 3.59 (dd, J 11.7, 3.2 Hz, IH), 3.57-3.50 (m, 2H), 3.22-3.14 (m, 2H), 2.99 (s, 6H), 1.33 (s, 9H). LCMS (ES+) 463 (M+H)+.

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, 832715-99-8, 6-(tert-Butyl)nicotinic acid.

Reference:
Patent; UCB PHARMA S.A.; ALI, Mezher, Hussein; BROWN, Julien, Alistair; DE CANDOLE, Benjamin, Charles; HUTCHINSON, Brian, Woodside; LANGHAM, Barry, John; NEUSS, Judi, Charlotte; QUINCEY, Joanna, Rachel; TREVITT, Graham, Peter; WO2010/146351; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6515-09-9, 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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

In a 2000-liter reactor, 546 kg of methanol, 182 kg of 2,3,6-trichloropyridine, 0.546 kg of 5% palladium-carbon (55% water), 28 kg of magnesium hydroxide and 46 kg of formic acid were added, and the mixture was stirred and heated up. At 40 degrees Celsius, nitrogen was replaced three times, and then hydrogen was introduced to maintain the pressure at 0.1-0.4 MPa. After 4 hours of reaction, the reaction was stopped to obtain a reaction solution. The reaction solution was filtered again, palladium carbon catalyst was recovered, and the first filtrate was obtained. The first filtrate was rectified and methanol was rectified for the next batch of cycle reactions. After the distillation of methanol is completed, water is added to the system to obtain a mixed and melted organic liquid of 2,3,6-trichloropyridine and 2,3-dichloropyridine.The organic liquid was slowly added dropwise to 182 kg of 25% hydrochloric acid, stirred at 5-10 degrees Celsius for 4 hours, and then pressure-filtered to recover 75 kg of unreacted 2,3,6-trichloropyridine and obtain the second filtrate. . At 10-15 degrees Celsius, 500 kg of water was added to the second filtrate to precipitate 2,3-dichloropyridine, which was filtered to give a product of 75 kg. In this embodiment, 5% palladium-carbon (water containing 55%) means that in the palladium carbon catalyst, the mass percentage of palladium is 5%, and the water content is 55%.Based on the improvement of the reaction process, the amount of palladium carbon catalyst used in the present invention is greatly reduced. The product was found to have a content of 2,3-dichloropyridine of 99% and a yield of 87%.

According to the analysis of related databases, 6515-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lier Chemical Co., Ltd.; Li Yuedong; Ren Jie; Li Jianwei; Liu Qiang; He Hongyun; (6 pag.)CN107721913; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59105-50-9, 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 59105-50-9 as follows.

General procedure: Pd(PPh3)4 (17.3 mg, 0.015 mmol) was added to a solution of 3-benzoy-5-bromo pyridine(130.1 mg, 0.5 mmol) and aryl boronic acid (0.6 mmol) in MeOH (0.2 mL), toluene (0.8 mL),and 2 M Na2CO3 (0.2mL) under N2. The mixture was heated to 75 C for 2 h, and then cooledto room temperature and concentrated under reduced pressure. Water was added to theresidue and the aq. phase was extracted with DCM (3 × 5 mL). The combined organic layerswere washed with brine, dried over Na2SO4, and evaporated to obtain the crude product.Purification by column chromatography on silica gel afforded the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59105-50-9, its application will become more common.

Reference:
Article; Fu, Yun; Sun, Jian; Molecules; vol. 24; 3; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 942189-65-3 , The common heterocyclic compound, 942189-65-3, name is 2-(6-Bromopyridin-3-yl)pyrimidine, molecular formula is C9H6BrN3, 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.

Refluxed mixture of 2-(6-Bromo-pyridin-3-yl)-pyrimidine (1Q) (200mg, 0.85mmol), N-tert-butoxycarbonyl-1 ,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester (290mg, 0.93mmol); Cesium Carbonate (500mg, 1.538mmol); PdCI2dppf (30mg) in dioxane/H2O (10ml v/v 4/1 ) for 4 hours. Cooled reaction, then evaporated solvent. Extracted with EtOAc (200ml) washed with H2O (50ml), dried over MgSO4, filtered and solvent evaporated yielding a solid which chromatographed on silica gel eluting with 30% v/v acetone/hexanes yielding 2Q as a white solid (110mg, 38%) ESMS (MH.339).

The synthetic route of 942189-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88312-64-5, Methyl 2-amino-5-nitronicotinate, 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: 88312-64-5, blongs to pyridine-derivatives compound. SDS of cas: 88312-64-5

2-Amino-5-nitro-nicotinic acid methyl ester (48.4mg, 0.245mmol) described in Preparation Example A-3 and lithium hydroxide monohydrate (10.3mg, 0.245mmol) were dissolved in a solvent mixture of tetrahydrofuran (1mL), methanol (0.1mL) and water (0.1 mL), and the solution was stirred for 17 hours at room temperature. The solvent was evaporated in vacuo, and 2-amino-5-nitro-nicotinic acid was obtained as a lithium salt. Then, the resulting lithium salt of 2-amino-5-nitro-nicotinic acid, C-(5-phenoxy-thiophen-2-yl)-methylamine (60mg, 0.29mmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (162mg, 0.367mmol) and triethylamine (103mul, 0.735mmol) were dissolved in N,N-dimethylformamide (2.0mL), and the solution was stirred for 6 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with water and brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1), and the title compound (87mg, 0.24mmol, 96%) was obtained as a pale yellow solid. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.49 (2H, d, J=5.5Hz), 6.50 (1H, d, J=3.7Hz), 6.80 (1H, d, J=3.1Hz), 7.08 (2H, d, J=7.7Hz), 7.13 (1H, t, J=7.5Hz), 7.37 (2H, t, J=7.5Hz), 8.76 (1 H, d, J=2.2Hz), 8.96 (1 H, d, J=1.7Hz), 9.51 (1 H, t, J=5.5Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88312-64-5, Methyl 2-amino-5-nitronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 33631-05-9, 2-Aminopyridin-4-ol, 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, 33631-05-9, blongs to pyridine-derivatives compound. Product Details of 33631-05-9

2-Amino-4-hydroxypyridine (4.4 g, 40.0 mmol)After dissolving in 200 mL of EtOH,Chloroacetaldehyde (16.5 mL, 100 mmol) was added,Stir the mixture overnight.The reaction solution was concentrated on a column chromatography to give white solid 6 imidazo [1,2-a] pyridine-7-ol in 88% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33631-05-9, its application will become more common.

Reference:
Patent; East China Normal University; Hu Wenhao; Xi Jianbei; Lei Ruirui; Zhu Mengli; Ma Mingliang; Xiao Guolan; Zhang Xiongwen; Fang Yanfen; Li Hongyu; (28 pag.)CN106496222; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem