Day: April 18, 2022

Application of 72583-83-6, 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.72583-83-6, name is 1-Methyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

In a vial, to a mixture of intermediate 5 (0.02 g, 0.07 mmol), 7-methoxy-4,5- dihydronaphtho[l,2-d]thiazol-2-amine (0.02 g, 0.07 mmol) was added BOP (0.030 g, 0.069 mmol), DMF (0.3 mL), and DIEA (0.060 ml, 0.35 mmol). After 72 h, the reaction mixture was filtered and subjected to reverse phase HPLC purification to afford Example 1 (4.4 mg, 9.9 %). NMR (500MHz, OMSO-d6) delta 8.34 – 8.04 (m, 2H), 7.85 – 7.81 (m, 1H), 7.80 – 7.73 (m, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.42 – 7.29 (m, 2H), 7.27 – 7.12 (m, 2H), 6.91 – 6.79 (m, 2H), 3.83 (s, 2H), 3.33 (br s, 1H), 3.02 – 2.93 (m, 2H), 2.92 – 2.84 (m, 2H), 3.77 (s, 3H). LCMS m/z = 505.0 (M+H)+; HPLC purity > 96% with retention time 1.81 min. [method A]

The chemical industry reduces the impact on the environment during synthesis 72583-83-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J. P.; (183 pag.)WO2019/14300; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (345.9 mg, 0.888 mmol) and 5-(trifluoromethyl)pyridin-3-amine (120 mg, 0.74 mmol) in pyridine (3 mL) was added POCl3 (227 mg, 1.48 mmol) dropwise. The mixture was stirred at 25 C. for 4 h and at 40 C. for 3 h. Sat. NaHCO3 was added to adjust the pH to 7-8 and the mixture was extracted with ethyl acetate (30 mL*2). The combined organic layers were dried over MgSO4, filtered and the filtrates were concentrated under reduced pressure to afford crude product as a yellow oil. The crude product was then purified by preparative HPLC (37% to 57% (v/v) CH3CN and H2O with 0.05% HCl) to afford 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-N-(5-(trifluoromethyl)pyridin-3-yl)-1H-pyrazole-4-carboxamide (130 mg, 37%). 1H NMR (400 MHz, DMSO-d6) delta ppm 5.67 (d, J=7.28 Hz, 1H), 7.26-7.31 (m, 1H), 7.68 (t, J=7.94 Hz, 1H), 7.94 (d, J=7.50 Hz, 1H), 8.44 (d, J=7.94 Hz, 1H), 8.53 (s, 1H), 8.60 (s, 1H), 8.75 (s, 1H), 9.12 (s, 1H), 11.18 (s, 1H), 11.64 (br d, J=4.63 Hz, 1H). LC-MS: (ES, m/z): [M+1]+ 467.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 83766-88-5, 2-(tert-Butoxy)pyridine, 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, 83766-88-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86847-84-9 , The common heterocyclic compound, 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide, molecular formula is C10H13ClN2O, 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.

A solution of 2-chloro-6pivaloylaminopyridine (10.5 g, 49.528 mmol) in THF (150 mL) is prepared under N2 and cooled to -80 0C. t-BuLi IM in pentane (108.962 mmol, 2.2 equiv.) is added carefully via an addition funnel under rigorously anhydrous conditions, over 1 hour. Once the addition is complete, the mixture is kept at -8O0C for 3 hours, at which point a solution of iodine (15.1 g, 59.431 mmol, 1.2 equiv.) in 50 mL THF under N2, is added slowly in one portion. After the addition, the cooling bath is removed and the reaction mixture allowed to warm up to room temperature under stirring for 2 hours. Finally the reaction mixture is quenched by slowly adding 50 mL of IM HCl. The mixture is then concentrated under vacuum to remove part of the THF, and the residue is partitioned between EtOAc and water. A 10% sodium thiosulfate solution is added until no further decolourisation occurred and that 2 clear phases are visible. The aqueous layer is extracted with EtOAc, the organic layers are gathered, washed with brine, dried over Na2Stheta4, and solvent is removed to afford an oil titrating 65 % of the desired material. This crude is refluxed in 100 mL of IM HCl and is refluxed for 5 hours at which point the depivaloylated product is completely formed. The pH is adjusted to 12 by slow addition OfNaHCO3 and extracted with DCM. The organic layer is concentrated and columned using 7/3 DCM/Cyclohexane as the eluent (Rf 9/21) to afford the title compound as an oil which solidified on standing

The synthetic route of 86847-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2008/65199; (2008); 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. 53710-18-2, name is 3,5-Diiodopyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3I2N

To a mixture of 4-(3-butenyloxy)-2,6-diethynylpyridine (4, 0.10 g, 0.51 mmol), 3,5-diiodopyridine (6, 0.63 g, 2.0 mmol), Pd(PPh3)4 (24 mg,21 mol), i-Pr2NH (2.5 mL), and THF (20 mL) was added CuI (3.9 mg, 20 mol), and the mixture wasstirred for 5 h at room temperature. The resulting mixture was treated with a Florisil bed and given a rinsewith AcOEt. The filtrate was concentrated by a rotary evaporator and the resulting residue was subjectedto silica gel column chromatography (eluent: CHCl3 to CHCl3/MeOH = 50:1) to give 7 as a colorless solid(0.16 g, 52%). Mp 196-198 C; IR (KBr) 3047, 2925, 2222, 1582, 1550 cm-1; 1H NMR (CDCl3) 2.57-2.64 (m, 2 H), 4.13 (t, J = 6.6 Hz, 2 H), 5.15-5.23 (m, 2 H), 5.82-5.95 (m, 1 H), 7.07 (s, 2 H), 8.21 (s,2 H), 8.73 (s, 2 H), 8.81 (s, 2 H); 13C NMR (CDCl3) 33.2, 67.8, 84.0, 92.1, 92.4, 113.9, 117.9, 120.8, 133.1,143.8, 146.6, 150.7, 155.2, 165.1; HRMS (ESI-TOF) calcd for C23H16I2N3O (M + H+): 603.9383; m/zfound: 603.9362.

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, 53710-18-2, 3,5-Diiodopyridine.

Reference:
Article; Abe, Hajime; Suzuki, Daiki; Shimizu, Ayako; Inouye, Masahiko; Heterocycles; vol. 88; 1; (2014); p. 547 – 557;,
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. 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

Synthesis of 1,1-dimethylethylcarbamate N-6-chloro-5-(trifluoromethyl)pyridin-3-yl, 6 (0080) (0081) The crude 6-chloro-5-(trifluoromethyl)pyridin-3-amine 5 (1.3 g crude. 6.61 mmol) is dissolved in pyridine (10 ml) and 4-dimethylaminopyridine (DMAP) (50 mg) is added. Di-tert-butyl dicarbonate (2.17 g) is added dropwise and mixture stirred at 22 C. for 4 hours. Toluene (20 ml) is added and all solvents is removed under reduced pressure. The residue is filtered through a plug of silica gel (hexane/ethyl acetate 2:1) to obtain tert-butyl N-6-chloro-5-(trifluoromethyl)pyridin-3-ylcarbamate 6.

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, 99368-68-0, 6-Chloro-5-(trifluoromethyl)pyridin-3-amine.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Jung, Michael E.; Sawyers, Charles L.; Ouk, Samedy; Tran, Chris; Wongvipat, John; (28 pag.)US9388159; (2016); B2;,
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.1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, molecular weight is 239.58, as common compound, the synthetic route is as follows.Formula: C8H5ClF3NO2

Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80 C. for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2×20 mL) and the combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (EI): m/e=262.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21901-41-7, 2-Hydroxy-4-methyl-5-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, 21901-41-7, blongs to pyridine-derivatives compound. Quality Control of 2-Hydroxy-4-methyl-5-nitropyridine

EXAMPLE 12 5-Methoxypyrrolo[2,3-c]pyridine (Compound 9) A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated atreflux under nitrogen for 52 hours. The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride. The residual oil then passed througha silica gel filter (dried at 150 C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1). This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95%) as an orange oil, which crystallized below 0 C.; IR (CHCl3) 1605, 1550, 1520, 1450, 1360, 1345 cm-1; 1 H NMR (CDCl3) delta 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100(55], 99 (74), 90 (43), 75 (36).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21901-41-7, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5051412; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7477-10-3 , The common heterocyclic compound, 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, molecular formula is C6H3ClN2O4, 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.

General procedure: A solution of compound 4 and different primary and secondary amines were stirred at rt for 1h, followed by extraction with EtOAc. The extract was then washed with 1N HCl, water, and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (hexane/EtOAc=2:1) to give product 6 as a solid. 4.2.4.3 6-(Benzylethylamino)-5-nitronicotinic acid (6c) Procedure A was used with compound 5 (405 mg, 2.0 mmol) and benzyl-ethyl-amine (540 mg, 4.0 mmol) to afford product 6c as a yellow solid (428 mg, 71%). 1H NMR (300 MHz, CDCl3) delta: 8.93 (s, 1H), 8.65 (s, 1H), 7.32-7.21 (m, 5H), 4.85 (s, 2H), 3.48 (q, J = 6.9 Hz, 2H), 1.22 (t, J = 6.9 Hz, 3H). ESI-MS: m/z (300, MH-).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18699-87-1, 2-Methyl-3-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, Computed Properties of C6H6N2O2, blongs to pyridine-derivatives compound. Computed Properties of C6H6N2O2

Step 2: 2-bromomethyl-3-nitropyridine; 2,2′-Azobis(isobutyronitrile) (2.7 g, 16.4 mmol) was added to a solution of2-methyl-3-nitropyridine (12.97 g, 92.6 mmol) prepared in Step 1 and N- bromo-succinimide (23.06 g, 130 mmol) in carbon tetrachloride (100 ml). The reactionmixture was refluxed for 3 days, cooled to room temperature, and then concentratedunder reduced pressure. The resulting residue was diluted with ethyl acetate (100 ml)and then washed with a saturated sodium bicarbonate solution and a saturated sodiumthiosulfate solution. The organic layer was dried on anhydrous magnesium sulfate andthen purified with purified with silica gel column chromatography(dichloromethane/n-hexane=2/l, v/v) to give 7.5 g of the titled compound as brown oil.lH-NMR(400MHz, CDCy 5 8.82(d, 1H), 8.39(d, 1H), 7.56(t, 1H), 5.07(s, 2H)

The synthetic route of 18699-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; JANG, Sun-Young; WO2006/25717; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem