Day: April 14, 2022

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

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

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

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

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

Related Products of 3430-18-0, 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 3430-18-0, name is 2,5-Dibromo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Method 3; Preparation of 6-bromo-5-methvmicotmaldehvde; 2,5-Dibromo-3-picoline (5.1 g, 20.30 mmol) in tetrahydrofuran (25 ml) was added dropwise to a 2M solution of isopropylmagnesium chloride (10.7 ml, 21.3 mmol) in tetrahydrofuran at 0 0C. The solution was stirred for 2 hours at 0 0C and then for 1 hour at ambient temperature. A solution of 4-formylmorpholine (2.1 ml, 20.3 mmol) in tetrahydrofuran (25 ml) was added dropwise and the solution stirred at ambient temperature for 1 hour. The solution was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulphate, filtered and the solution concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with 10 % ethyl acetate in isohexane, to give the title compound (3.0 g, 74 %); NMR Spectrum: (DMSO-d6) 2.44 (s, 3H), 8.19 (s, IH), 8.73 (s, IH), 10.09 (s, IH).

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 3430-18-0, 2,5-Dibromo-3-methylpyridine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/71956; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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