Day: August 26, 2021

Reference of 2002-04-2, 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.2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, molecular formula is C7H6N4S, molecular weight is 178.21, as common compound, the synthetic route is as follows.

General procedure: An equimolar amount of 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine (3c) dissolve in 10-15mL of tetrahydrofuran (THF), add 2-3 drops of triethylamine, to this solution add 1.5mol different aryl chlorides gradually, continuous stirring for 3h on ice bath(0C). After completion of reaction solid will precipitate out, washed with sodium bicarbonate solution to remove excess of chloride and recrystallized from ethanol to get pure compound.

The chemical industry reduces the impact on the environment during synthesis 2002-04-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Patel, Harun; Jadhav, Harsha; Ansari, Iqrar; Pawara, Rahul; Surana, Sanjay; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 1 – 9;,
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. 16867-03-1, name is 2-Amino-3-hydroxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, 15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, [0294] 5.1 g of 5% rhodium/ carbon catalyst are added and the mixture is hydrogenated in a 600 ml vessel (material: Hastelloy) at room temperature (20 C.) at 4.5 bar for about 16 hours. The entire reaction mixture is then filtered (removal of the catalyst) and concentrated under reduced pressure, and the residue that remains is recrystallized from an ethanol/ether mixture. This gives 5.9 g (23.9% of theory) of a (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate CH NMR spectrum: some Py-H) which can be used for the next reaction. [0295] 1H NMR (600 MHz, D2O) delta 1.79 (br., m, 1H), 1.90-1.92 (m, 1H), 1.99-2.00 (br., m, 1H), 2.22 (br., m, 1H), 3.37 (m, 2H), 4.52 (m, 1H), 6.77-6.78 (m, 1H), 7.18-7.19 (m, 1H), 7.28-7.29 (m, 1H) ppm; At room temperature, 1.0 g (5.74 mmol) of the (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate (cf. step 1) are stirred with 1.26 g (7.79 mmol) of 1,1?-carbonyldiimidazole (CDI), 39.9 mg of 4-dimethylaminipyridine (DMAP) in 6 ml of dichloromethane, and 1.2 ml of triethylamine are added. The entire reaction mixture is then stirred at room temperature for another about 24 hours. The reaction mixture is then concentrated under reduced pressure, the residue that remains is taken up in ethyl acetate and the organic phase is washed with water. The organic phase is separated off and then dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue that remains is purified chromatographically by medium-pressure chromatography (cyclohexane/acetone gradient). This gives 753.0 mg (93.2% of theory) of a mixture of oxazolo[4,5-b]-5,6,7,7a-tetrahydropyridin-2(4H)-one [0301] and oxazolo[4,5-b]pyridin-2(3H)-one (cf. WO 2010/135014 A1) (1H NMR spectrum: some Py-H and LC-MS m/z: 137.0) which can be used for the next reaction. [0302] LC-MS (ESI positive): m/z found: 141.0 [M++H]. [0303] C6H8N2O2 calculated: 140.0.

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, 16867-03-1, 2-Amino-3-hydroxypyridine.

Reference:
Patent; Jeschke, Peter; Schindler, Michael; Woelfel, Katharina; Ebbinghaus-Kintscher, Ulrich; Voerste, Arnd; Malsam, Olga; Losel, Peter; Goergens, Ulrich; US2014/113824; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 126325-47-1 ,Some common heterocyclic compound, 126325-47-1, molecular formula is C6H7BrN2, 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.

Preparation VI; 6-Cyano-2-methyl-3-aminopyridine; A mixture of 3.5 g (18.6 mmol) of 6-bromo-2-methyl-3-aminopyridine, 352 mg (0.37 mmol) of tris(benzylideneacetone)dipalladium(0), 532 mg (0.92 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 146 mg (2.2 mmol) of zinc powder and 1.4 g (12 mmol) of zinc cyanide in 70 ml of N,N-dimethylacetamide is prepared and the reaction mixture is then stirred at 20 C. for 22 hours. It is diluted with 200 ml of ethyl acetate and washed with 2 N ammonium chloride solution. (Decantation is obtained only after filtration of the mixture on a filter aid of the Celite type.) The organic phase obtained is washed with sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (9/1; v/v) as the eluent to give 1.6 g of the expected compound in the form of a yellow powder (yield=65%). M.p.=192-196 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,126325-47-1, its application will become more common.

Reference:
Patent; Laboratoires Fournier S.A.; US2007/54955; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10128-91-3 ,Some common heterocyclic compound, 10128-91-3, molecular formula is C7H7NO3, 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: 2-Hydroxynicotinic acid methyl ester (CAS number 10128-91-3) (100-200 mg scale), the corresponding aryl iodide (0.95 equiv), CuBr (10 mol%), 2-ethylester cyclohexanone (20 mol%) and Cs2CO3 (2.2 equiv) were suspended in DMSO (anhydrous, 2-3 mL) in a sealed tube. The reaction was complete after about 18 h heating at 60 C. The mixture was diluted in EtOAc and washed with brine. The aqueous phase was re-extracted once with EtOAc. The combined organic phases were dried over anhydrous MgSO4, and the solids filtered off. The solvent was removed in vacuo and the resulting crude material purified by column chromatography over lica gel, EtOH/CH2Cl2. The products were isolated in good yields (53-58%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10128-91-3, its application will become more common.

Reference:
Article; Suarez, Rosa M.; Chevot, Franciane; Cavagnino, Andrea; Saettel, Nicolas; Radvanyi, Francois; Piguel, Sandrine; Bernard-Pierrot, Isabelle; Stoven, Veronique; Legraverend, Michel; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 2 – 25;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15506-18-0, 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.15506-18-0, name is 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C7H7NO3, molecular weight is 153.1354, as common compound, the synthetic route is as follows.

b) 3-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9- diazaspiro[5.5]undec-3-yl}carbonyl)-1-methylpyridin-2(lH)-oneN-methyl-2-hydroxynicotinic acid (45 mg, 0.29 mmol), Intermediate A (76 mg, 0.24 mmol), HATU (91.9 mg, 0.24 mmol) and triethylamine (43 mg, 0.43 mmol) in CH2Cl2 (4 mL) were mixed and stirred for Ih. The reaction mixture was diluted with saturated aqueous sodium carbonate (2 mL) and the product was extracted with dichloromethane and dried. The pure title compound was obtained by preparative HPLC.1H NMR (399.99 MHz, CD3OD) delta 7.81-7.71 (m, IH), 7.60-7.52 (m, IH), 7.32-7.26 (m, IH), 7.23-7.16 (m, IH), 6.97-6.88 (m, IH), 6.48-6.36 (m, IH), 4.32-4.19 (m, 2H), 3.79- 3.67 (m, 2H), 3.62-3.55 (m, 3H), 3.45-3.35 (m, 2H), 3.26-3.06 (m, 4H), 2.08-1.96 (m, 2H), 1.84-1.37 (m, 14H)APCI-MS m/z: 450.5 [MH+]HPLC (Method A) Retention time: 5.63 minHPLC (Method B) Retention time: 7.07 min

The chemical industry reduces the impact on the environment during synthesis 15506-18-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2007/30061; (2007); A1;,
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 86718-01-6, name is Methyl imidazo[1,2-a]pyridine-7-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 86718-01-6

Hydrazine monohydrate (10 ml, 636 mmol) was added to methyl imidazo[1,2-a]pyridine-7-carboxylate (CAS: 86718-01-6) (11.2 g, 63.57 mmol) in solution in MeOH (300 ml). The reaction mixture was refluxed for 3 hours, then additional hydrazine monohydrate (10 ml, 636 mmol) was added and the mixture was refluxed overnight. After cooling to room temperature, the precipitate was filtered, washed with EtOH and dried yielding 13 g (quantitative) of intermediate shown.

With the rapid development of chemical substances, we look forward to future research findings about 86718-01-6.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2012/41000; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 127406-56-8, 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 127406-56-8 as follows.

EXAMPLE 5; Synthesis of 3-hydroxy-4-(pyridine-2-yl)benzaldehyde (5a)In a 20 mL tube, 4-(pyridine-2-yl)benzaldehyde (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H2O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 36 h. The reaction mixture was diluted with 20 mL Of CH2Cl2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. After purification by column chromatography on silica gel with a gradient eluent of hexane and ether (Rf = 0.29 in 2:1 hexane: ether), the title product was obtained as a pale yellow solid (25.7 mg, 43%). 1H NMR (400 MHz, CDCl3) delta 14.59 (s, IH), 10.00 (s, IH), 8.58 (d, J = 4.8 Hz, IH), 8.02-7.92 (m, 3H), 7.50 (s, IH), 7.44 (d, J= 8.4 Hz, IH), 7.36 (t, J= 7.2 Hz, IH); 13C NMR (100 MHz, CDCl3) delta 191.93, 160.41, 156.55, 146.09, 138.34, 138.15, 126.74, 123.73, 122.75, 120.49, 120.01, 118.71; IR (thin film) v 3055, 1698, 1594, 1419, 1265 cm”1; HRMS (TOF) Calcd for C12Hi0NO2 (M + H) 200.0712, found 200.0708.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127406-56-8, its application will become more common.

Reference:
Patent; BRANDEIS UNIVERSITY; WO2007/123910; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885277-08-7, Adding some certain compound to certain chemical reactions, such as: 885277-08-7, name is 5-Chloropyridine-2-sulfonyl chloride,molecular formula is C5H3Cl2NO2S, 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 885277-08-7.

To a solution of Example 3B (60.0 mg, 0.187 mmol) and 5-chloropyridine-2-sulfonyl chloride (43.6 mg, 0.205 mmol) in N,N-dimethylformamide (1.5 mL) was added triethylamine (0.065 mL, 0.467 mmol). The mixture was stirred for 2 hours, quenched with saturated NaHC( and brine, and extracted with ethyl acetate (2x). The combined organic layers were concentrated, and the residue was purified by reverse-phase HPLC (see protocol in Example 273E) to provide the title compound (26.7 mg, 31 %). JH NMR (500 MHz, DMSO-<) delta ppm 9.05 (s, 1H), 8.85 (dd, J = 2.5, 0.7 Hz, 1H), 8.65 (s, 1H), 8.24 (dd, J = 8.4, 2.4 Hz, 1H), 8.00 (dd, J = 8.4, 0.7 Hz, 1H), 7.48 (t, J = 8.8 Hz, 1H), 7.03 (dd, J = 11.3, 2.9 Hz, 1H), 6.81 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.42 (s, 2H), 1.96 (s, 6H); MS (ESI+) m/z 460.3 (M+H)+. 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. 885277-08-7, 5-Chloropyridine-2-sulfonyl chloride, other downstream synthetic routes, hurry up and to see. Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; PLIUSHCHEV, Marina, A.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; SWEIS, Ramzi, Farah; DART, Michael, J.; RANDOLPH, John, T.; MURAUSKI, Kathleen; (674 pag.)WO2019/90076; (2019); 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. 1702-17-6, name is 3,6-Dichloropicolinic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 3,6-Dichloropicolinic acid

Under a nitrogen atmosphere, (Purity: 95.1 wt%) of 3,6-dichloropyridine-2-carboxylic acid, 63 g of toluene and 0.48 g of N, N-dimethylformamide was added dropwise at 80 C over 0.5 hour And 17.04 g of thionyl chloride was added thereto, followed by stirring at the same temperature for 1.5 hours. The reaction mixture was cooled to 50 C and concentrated under reduced pressure to give 47.67 g of a toluene solution of 3,6-dichloropyridine-2-carboxy chloride (confirmed by mixing the reaction mixture with methanol).

The synthetic route of 1702-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; KIMURA, TAKAHIRO; MAEHATA, RYOTA; (41 pag.)TW2016/5803; (2016); A;,
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.15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, molecular weight is 281.89, as common compound, the synthetic route is as follows.Computed Properties of C5H2Br2N2O2

To a stirred solution of 2,5-dibromo-3-nitropyridine (226 mg, 0.802 mmol), (4- (1 ,4-dimethyl- 1H- 1 ,2,3-triazol-5-yl)-3-fluorophenyl)boronic acid (282.6 mg, 1.20 mmol),and PdC12(dppf) (29.3 mg, 0.040 mmol) in THF (8.0 mL) was added tripotassium phosphate (3M in H20, 802 pi, 2.41 mmol), purged with N2 (vacuum/N2 x3) and the reaction was heated at 75 C with stirring for 1 h. The reaction was cooled to room temperature and concentrated. The residue was suspended in EtOAc, filtered throughCelite, washed with EtOAc, concentrated. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0% to 100% using solvent A/B=CH2C12/EtOAc over 15 column volumes, RediSep Si02 40 g, loaded as DCM solution). Obtained the product (190 mg, 61%): HPLC: RT=0.91 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.1%TFA, 1.5 mm gradient,wavelength=254nm); MS (ES): m/z=392 [M+1f

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15862-37-0, 2,5-Dibromo-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUESNELLE, Claude A.; HARIKRISHNAN, Lalgudi S.; HILL, Matthew D.; (180 pag.)WO2016/183114; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem