Month: March 2022

Application of 956010-87-0 ,Some common heterocyclic compound, 956010-87-0, molecular formula is C7H4F3N3, 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 mixture of compound 12 (50 mg, 0.27 mmol), benzylbromide (50 mg, 0.29 mmol) and caesium carbonate (104 mg, 0.32 mmol) was stirred overnight at room temperature in DMF (1.0 mL). It was then diluted with tert-butyl methyl ether and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated. The crude product was purified by column chromatography (eluent: cyclohexane/ethyl acetate 3:1) to yield 50 mg (67 %) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta 5.82 (s, 2H), 7.26-7.37 (m, 5H), 7.50 (dd, J=8.2, 4.5Hz, 1H), 8.39 (d, J=8.2Hz, 1H), 8.79 (dd, J=4.5, 1.2Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta 50.8, 111.4 (q, 1JC,F=1.4Hz), 119.7, 121.4 (q, 1JC,F=269Hz), 127.7, 127.9, 128.7, 129.3, 131.5 (q, 2JC,F=38.6 Hz), 136.2, 149.8, 151.0. HRMS m/z calcd for C14H10F3N3: 277.0827; found: 277.0825.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,956010-87-0, its application will become more common.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)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, Quality Control of 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, blongs to pyridine-derivatives compound. Quality Control of 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used ?as is? in the step of Example 3 below. ; Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,179687-79-7, 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, 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: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

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. 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6938-06-3, 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 6938-06-3, name is Butyl nicotinate. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL),then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.

According to the analysis of related databases, 6938-06-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Ning; Sheng, Jun-Feng; Song, Fei; Tong, Yu-Zhu; Wang, Zuo-Xiang; Russian Journal of General Chemistry; vol. 85; 3; (2015); p. 746 – 751;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100155-73-5 , The common heterocyclic compound, 100155-73-5, name is 1-(2-Pyridyl)-1-propylamine, molecular formula is C8H12N2, 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.

To a 8 mL vial charged with imidazole (17.3 mg, 0.26 mmol) and tert-butyl (6-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)(ethyl)carbamate (26.5 mg, 0.051 mmol) in DCM (1ml) was added 1,1′-carbonyldiimidazole (25 mg, 0.153 mmol). The reaction mixture was stirred at room temperature for 5 h, leading to a clear yellow solution. A solution of 1-(pyridin-2-yl)propan-1-amine, 2HCl (21.33 mg, 0.102 mmol) and DIEA (0.045 ml, 0.255mmol) in DMF (1 ml) was added. The vial was capped and the contents stirred at room temperature for 16 h. The reaction mixture was concentrated and the resulting residue redissolved in TFA (1 ml) and stirred at room temperature for 20 minutes. Triethylsilane (0.008 ml, 0.051 mmol) was added dropwise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford 1-(3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-(pyridin-2-yl)propyl)urea (4.1 mg, 0.012 mmol, 23.69 % yield) as a white solid.

The synthetic route of 100155-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WILSON, Kevin, J.; WITTER, David, J.; SILIPHAIVANH, Phieng; LIPFORD, Kathryn; SLOMAN, David; FALCONE, Danielle; O’BOYLE, Brendan; MANSOOR, Umar Faruk; LIM, Jongwon; METHOT, Joey, L.; BOYCE, Christopher; CHEN, Lei; DANIELS, Matthew, H.; FEVRIER, Salem; HUANG, Xianhai; KURUKULASURIYA, Ravi; TONG, Ling; ZHOU, Wei; KOZLOWSKI, Joseph; MALETIC, Milana, M.; SHINKRE, Bidhan, A.; THATAI, Jayanth Thiruvellore; BAKSHI, Raman Kumar; KARUNAKARAN, Ganesh Babu; WO2014/52563; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 121643-44-5, 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 121643-44-5 as follows.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1 H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,121643-44-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3, 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 1018505-59-3 as follows.

General procedure: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 874-10-2, 8-Methylimidazo[1,2-a]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, Quality Control of 8-Methylimidazo[1,2-a]pyridine, blongs to pyridine-derivatives compound. Quality Control of 8-Methylimidazo[1,2-a]pyridine

1 g of 8-methylimidazo[1,2-a]pyridine [3-1] was dissolved in 20 mL of 1-butanol, and a catalytic amount of Raney nickel of was added thereto. The mixture was stirred under a hydrogen atmosphere (5 atmospheric pressure) at 65C for 4 days. After cooling the reaction mixture back to room temperature, the insolubles were filtered through celite, and washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 823.3 mg of 8-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [46-1].

The synthetic route of 874-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1790650; (2007); 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. 4214-74-8, name is 3,5-Dichloropyridin-2-amine. A new synthetic method of this compound is introduced below., name: 3,5-Dichloropyridin-2-amine

Example 605-Cyano-furan-2-carboxylic acid[4-methyl-5′-(4-methyl-piperazin-l-yl)-3,4,5,6- tetrahydro-2H-[l,3′]hipyridinyl-2 ‘-yl]-amide a) 3,5-dicholoro-2-nitro pyridine; 2-Amino-3,5-dichloropyridine (193 mg, 1.00 mmol) was dissolved in cone H2SO4 (5 mL) and K2S2O8 (1.3 g, 5.0 mmol) was added portionwise. The resulting mixture was stirred at RT overnight and poured onto crushed ice and neutralized with’satd aq NaHCO3. EPO The product was extracted with CH2Cl2 (3×20 mL), dried (Na2SO4) and concentrated in vacuo to obtain the title compound (123 mg, 63.7%). 1H-NMR (CDCl3; 400 MHz): delta 8.40 (d, IH , J= 2.1 Hz), 8.05 (d, IH, J= 2.1 Hz).

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, 4214-74-8, 3,5-Dichloropyridin-2-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5, Adding some certain compound to certain chemical reactions, such as: 195044-14-5, name is 2-Bromo-6-tert-butylpyridine,molecular formula is C9H12BrN, 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 195044-14-5.

Step-1: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (400 mg, 1.78 mmol, 1.0 eq) and 2-bromo-6-(tert-butyl)pyridine (458 mg, 2.14 mmol, 1.20 eq) in (12 mL) of dioxane was added potassium carbonate (492 mg, 3.56 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (68 mg, 0.356 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (63 mg, 0.712 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired product, 1-(6-(tert-butyl)pyridin-2-yl)-2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (366 mg, 57.40%) as colorless liquid. LCMS: 358.2 [M+1]+

According to the analysis of related databases, 195044-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem