Day: June 11, 2021

Synthetic Route of 18615-86-6 ,Some common heterocyclic compound, 18615-86-6, molecular formula is C6H7NO, 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 1 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy)-2-methylpyridine 2-Methylpyridin-4-ol (60 mg, 0.55 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 mL), and potassium carbonate (75.5 mg, 0.55 mmol) and (3R,4aR,6aS,7R,10bR)-7-(2-bromoethyl)-3-cyclopentyl-6a,10b-dimethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin (150 mg, 0.37 mmol) were successively added to the reaction solution and stirred overnight at 60 C. The reaction solution was cooled and extracted with dichloromethane (30 mL). The organic layer was washed with water (10 mL*3), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure and then separated by column chromatography to give 4-(2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-dihydromethylene decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethoxy)-2-methylpyridine 319 (80 mg, yield: 50%). MS m/z (ESI): 440.8 [M+1] 1H NMR (400 MHz, CDCl3) 8.31 (d, J=6.0 Hz, 1H), 6.67-6.64 (m, 1H), 4.91 (s, 1H), 4.63-4.60 (m, 2H), 4.10-3.88 (m, 3H), 3.53-3.45 (m, 2H), 2.54 (s, 3H), 2.46-1.56 (m, 18H), 1.55 (s, 3H), 1.39-1.27 (m, 3H), 0.81 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18615-86-6, its application will become more common.

Reference:
Patent; Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.; MEDSHINE DISCOVERY INC.; HE, Haiying; JIANG, Zhigan; XIA, Jianhua; WANG, Jing; HAN, Lixia; LAN, Lihong; ZHOU, Hui; LAI, Kunmin; CHEN, Shuhui; US2018/346438; (2018); 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 6937-03-7, name is Methyl 2-aminoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H8N2O2

Methyl 2-aminopyridine-4-carboxylate (2 g, 13.14 mmo 1, 1.00 equiv) wasdissolved in tert-butano 1 (20 mL) after which di-tert-butyl dicarbonate (4.02 g, 18.42mmol, 1.40 equiv) was added. The reaction mixture was agitated at 60C overnight then the reaction was halted through the addition of an aqueous 1M NaHCO3 solution (50 mL). The solid was recovered by filtration, washed with 50 mL of EtOH then dried in vacuo to yield 2.5 g (75 %) of compound 2E in the form of a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 6937-03-7.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89937-77-9, 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 89937-77-9 as follows.

Step 1 4-Hydroxymethyl-1H-pyridin-2-one 2-Oxo-1,2-dihydropyridine-4-carboxylic acid methyl ester (1.8 g, 12.2 mmol), prepared as described in J. Org. Chem., 26, 428 (1961), was suspended in THF(100 ml). A small amount of DMF was added to help increase solubility. LiBH4 (61 mmol) was added and the reaction was stirred for 18 hours at room temperature. MeOH and H2 O are added to quench the reaction. The reaction is then concentrated to yield a yellow oil. Flash chromatography (5% MeOH/CHCl3 to 20% MeOH/CHCl3) yielded 4-hydroxymethyl-1H-pyridin-2-one as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.38-7.36 (1H,d); 6.56 (s, 1H); 6.37-6.36 (d, 1H); 4.50 s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89937-77-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6093737; (2000); 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.58584-63-7, name is (6-Methoxypyridin-3-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Quality Control of (6-Methoxypyridin-3-yl)methanol

To a stirred solution of (6-methoxypyridin-3-yl)methanol (49.8 mg, 0.358 mmol) in DMF (0.5 ml.) at 0 C was added sodium hydride (60% dispersion in mineral oil) (10.73 mg, 0.447 mmol) and the reaction mixture stirred for 15 min prior to the addition of 4- methylbenzene-l-sulfonyl chloride (85 mg, 0.447 mmol). The reaction was stirred for a further 30 min at this temperature. In a separate flask, 5-(4-chloro-lH-imidazol-2-yl)-l,3- dimethylpyridin-2(lH)-one (for an example preparation, see Intermediate 12, 40 mg, 0.179 mmol) was dissolved in DMF (0.5 ml.) at 0 C, to which sodium hydride (60% dispersion in mineral oil) (8.58 mg, 0.358 mmol) was added and the reaction stirred for a further 30 min. The solution containing the tosylated pyridine was added dropwise to the flask containing the imidazole, and the reaction stirred for a further 16 h. The solvent was removed in vacuo and the crude product was purified by MDAP (Method A) to afford the title compound as a colourless film (16 mg, 0.04 mmol, 23%). LCMS (System A): tRET = 0.79 min; MH+ 345.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-63-7, (6-Methoxypyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 882521-63-3, 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. 882521-63-3, name is 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine. A new synthetic method of this compound is introduced below.

General procedure: To a microwave tube was added [1,2,4]triazolo[1,5-a]pyridin-2-amine 13 (1 equiv), K2CO3 (2.0 equiv), Pd(PPh3)4 (0.056 equiv), and the corresponding boronic acid (1.5 equiv). 5 mL of EtOH:H2O (1:1) was used as solvent, and the microwave conditions employed were 150 C for 30 min. After solvent evaporation, the product was purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 – 100%) in n-hexane or MeOH (0 – 10%) in DCM to afford the desired compound 16 (adapted from 4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,882521-63-3, 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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.

(5-((3-bromophenoxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (0.300 g, 0.932 mmol) was reacted with imidazo[l,2-a]pyridine-6-carboxylic acid (0.181 g, 1.119 mmol) in the presence of BOP reagent (0.452 g, 1.025 mmol) and Nu,Nu- diisopropylethylamine (0.359 g, 2.790 mmol) in Nu,Nu-dimethylformamide (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (methanol/dichloromethane = 2/98) to give titled compound (0.250 g, 62 %) as a solid. LCMS: m/z 429.3 [M+H] +; lU NMR (300 MHz, Chloroform-d) delta 8.83 (m, 1H), 7.73 – 7.62 (m, 3H), 7.44 (dd, / = 9.4, 1.8 Hz, 1H), 7.15 – 7.04 (m, 2H), 6.90 – 6.79 (m, 2H), 5.07 – 4.98 (m, 1H), 4.43 (d, / = 5.3 Hz, 2H), 4.06 (d, / = 4.7 Hz, 2H), 3.25 (dd, / = 17.3, 10.7 Hz, 1H), 3.09 (dd, / = 17.3, 7.2 Hz, 1H).

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 139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 845306-08-3, 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.845306-08-3, name is tert-Butyl 5-bromopicolinate, molecular formula is C10H12BrNO2, molecular weight is 258.11, as common compound, the synthetic route is as follows.

A 20 mL sealed tube was charged with tris(dibenzylideneacetone)dipalladium(0) (0.049 g, 0.053 mmol), tri-teri-butylphosphonium tetrafluoroborate (Strem, 0.037 g, 0.127 mmol), tert- butyl 5-bromopicolinate (Combi-Blocks, 0.456 g, 1.767 mmol), and N,N-dimethylformamide (8.8 mL). The tube was purged with a nitrogen stream for 2 minutes, sealed and stirred at ambient temperature. 2-cyanoethylzinc bromide (0.5 M in tetrahydrofuran, 4.77 mL) was added dropwise over 2 minutes via a cannula needle. The reaction mixture was stirred at ambient temperature for 6 hours and then at 75 C for 18 hours. The reaction was cooled to ambient temperature and quenched with water (0.5 mL), and the resulting mixture was concentrated under reduced pressure briefly to remove most of the tetrahydrofuran solvent. The resulting solution was filtered through a glass microfiber frit and directly purified by reverse -phase flash chromatography [150 g Redisep Gold C18 column, flow rate 110 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (0.15 g, 0.65 mmol, 37% yield). MS (ESI+) m/z 233 (M+H)+.

Statistics shows that 845306-08-3 is playing an increasingly important role. we look forward to future research findings about tert-Butyl 5-bromopicolinate.

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

Adding a certain compound to certain chemical reactions, such as: 3939-13-7, 2-Fluoronicotinonitrile, 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 C6H3FN2, blongs to pyridine-derivatives compound. Computed Properties of C6H3FN2

Synthesis of intermediate VX001: Isoxazolo[5,4-b]pyridin-3-amine 909 mg (8.1 mmol) of KO-t-Bu were added, with vigorous stirring, to a suspension of 668 mg (8.9 mmol) of acethydroxamic acid in DMF (20 ml), and the mixture was stirred for 30 min at RT. 990 mg (8.1 mmol) of 2-fluoro-nicotinonitrile were then added, and stirring was carried out for a further 5 h at 50 C. The mixture was then extracted with EA and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 305 mg (2.3 mmol, 28%) of isoxazolo[5,4-b]pyridin-3-amine.

The synthetic route of 3939-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUNENTHAL GMBH; US2010/234419; (2010); A1;,
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. 42753-71-9, name is 2-Amino-5-bromo-6-methylpyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H7BrN2

Example A3 A 0 C. solution of sulfuric acid (125 mL) was treated drop-wise with H2O2(30%, 63.1 mL, 2058 mmol), stirred for 15 min, treated drop-wise with a cold solution of 6-amino-3-bromo-2-picoline (35 g, 187 mmol) in sulfuric acid (125 mL), allowed to warm to RT and stirred for 4 h. The mixture was poured onto ice (1.2 kg) and the resulting solid collected via filtration, dissolved in DCM, washed with brine, dried over Na2SO4 and concentrated to dryness. The aqueous filtrate and washes were combined, extracted with DCM (2*) and the combined organics were dried over Na2SO4, concentrated to dryness, purified via silica gel chromatography (EtOAc/Hex) and combined with the above-isolated solid to afford 3-bromo-2-methyl-6-nitropyridine (25.59 g, 63%). MS (ESI) m/z: 218.9 (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, 42753-71-9, 2-Amino-5-bromo-6-methylpyridine.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); 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. 180748-30-5, name is (4-Chloropyridin-2-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 180748-30-5

[0411] To (4-chloro-2-pyridyl)methanamine (59, 0.51 g, 3.58 mmol) in dichloromethane (50 mL) was added l-isothiocyanato-4-nitro-benzene (65, 0.66 g, 3.65 mmol). The reaction mixture was stirred at room temperature for about 1 hour. LCMS showed the reaction was complete. The reaction was concentrated, and washed with ethyl acetate and hexane to give product (63).

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, 180748-30-5, (4-Chloropyridin-2-yl)methanamine.

Reference:
Patent; PLEXXIKON INC.; ZHANG, Jiazhong; POWERS, Hannah; ALBERS, Aaron; PHAM, Phuongly; WU, Guoxian; BUELL, John; SPEVAK, Wayne; GUO, Zuojun; WALLESHAUSER, Jack; ZHANG, Ying; (229 pag.)WO2019/183145; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem