Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 103057-10-9, name is 4-(Chloromethyl)-1-trityl-1H-imidazole, belongs to imidazoles-derivatives compound, 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 103057-10-9, COA of Formula: C23H19ClN2

Example 8 Preparation of bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate: To a solution of bis(2,2,2-trifluoroethyl)phosphite (0.11 ml, 0.6 mmol) in THF (1.5 ml) were added 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) (0.09 ml, 0.6 mmol) and (1-triphenylmethylimidazol-4-yl)methyl chloride (71.8 mg, 0.2 mmol). The reaction mixture was refluxed under argon flow for 22 hours. The solvent was removed under reduced pressure, and water (10 ml) was added to the residue, which was then extracted 3 times with ethyl acetate (10 ml). The resultant organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained white solid was purified through chromatography on silica gel column using ethyl acetate – hexane (3:2) to give bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate (34 mg, 30%) as a white powder. This powder was recrystallized from a mixture of ethyl acetate and hexane to provide a white small needle crystal (m.p. 145-148C). 1H NMR (CDCl3) d 3.34 (d, J = 10.5 Hz, 2H), 4.30 (quint, d, J = 3.9 Hz, 1.3 Hz, 4H), 6.80 (s, 1H), 7.08-7.50 (m, 16H). 31P NMR(CDCl3) d 29.9 (s). Anal Calcd for C27H23N2O3PF6: C, 57.03; H, 4.08; N, 4.93. Found: C, 57.03; H, 4.19; N, 4.94.

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.

Reference:
Patent; Azwell Inc.; EP1477487; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 3314-30-5 as follows. name: 1H-Benzo[d]imidazole-2-carbaldehyde

General procedure: The appropriate imidazolecarboxaldehyde derivative (10 mmol, 1 equiv.) was dissolved inmethanol. The amine (1 equiv.) in dry THF (5.0 mL), and activated 4 molecular sieves (2.00 g) wereadded. The reaction mixture was stirred at room temperature, under nitrogen for 12 hours. Then,sodium borohydride (1.2 equiv.) was added portionwise and the reaction was stirred at roomtemperature. After 3 hours water was added, and the mixture was stirred for 10 minutes. Molecular sieves were filtered off through a Celite pad. The filtrate was evaporated under reduced pressure.The residue was taken up with EtOAc and the organic layer was washed with 2N NaOH ( ¡Á 1), driedover sodium sulfate and concentrated in vacuo. The crude material was purified by columnchromatography using the indicated eluents

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Galli, Ubaldina; Hysenlika, Rejdia; Meneghetti, Fiorella; Grosso, Erika Del; Pelliccia, Sveva; Novellino, Ettore; Giustiniano, Mariateresa; Tron, Gian Cesare; Molecules; vol. 24; 10; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 10394-38-4, A common heterocyclic compound, 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, molecular formula is C8H9N3, 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 suspension of 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-l- yl)pyridazine-3-carbonitrile (285.8 mg, 0.82 mmol) and l-methyl-li7-benzo[Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, 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 288-32-4 as follows.

To a solution of 1H-Imidazole (5 g, 73.5 mmol) in THF was added sodium hydride (1.8 g, 45 mmol) and stirred at room temperature for 0.5 hour before addition of then bromo-acetonitrile (8.8 g, 73.9 mmol) and stirring at room temperature for 2 hours. The reaction was quenched via the addition of water (50 mL) and saturated ammonium chloride (50 mL) solution and the mixture was extracted with ethyl acetate (100 mL*3). The combined organics layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude residue was purified on silica gel (petroleum ether:ethyl acetate=10:1) to afford 2-(1H-imidazol-1-yl)acetonitrile (4.6 g, 59%) as a yellow oil. LRMS m/z: 108 [M+H+].

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Albrecht, Brian K.; Bellon, Steven F.; Gehling, Victor S.; Harmange, Jean-Christophe; LeBlanc, Yves; Liang, Jun; Magnuson, Steven; Tsui, Vicki; Zhang, Birong; US2015/65522; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 288-32-4 as follows. HPLC of Formula: C3H4N2

To a solution of imidazole (13.6 g, 0.2 mol) in 1 L of DCM was added BrCN (7.4 g, 66 mmol), and the mixture was heated at reflux for 30 minutes. The mixture was cooled to RT, and the white precipitate removed by filtration, and the filtrate concentrated to 100 mL then cooled to 0 C. for 2 days. The crystallized solid was filtered and washed with cold DCM, then dried in vacuo to give the desired product (8.8 g) as a white solid.

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 106429-59-8, 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. 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Step 4.5-((7-(5-((5-fluoro-2′-isopropyl-[1,1′-biphenyl]-2-yl)oxy)pyrimidin-4-yl)-2,7- diazaspiro[4.4] nonan-2-yl)methyl)-1H-benzo[d]imidazol-2(3H)-one (0987) A mixture of 2-(5-((5-fluoro-2′-isopropyl-[1,1′-biphenyl]-2-yl)oxy)pyrimidin-4- yl)-2,7-diazaspiro [4.4]nonane (6.8 g, 15.7 mmol), 2-oxo-2,3-dihydro-1H- benzo[d]imidazole-5-carbaldehyde (Intermediate 40, 3.05 g, 18.8 mmol), NaBH3CN (3.9 g, 62.8 mmol) and HOAc (3.4 mL) in MeOH (130 mL) was stirred at 70 C for 18 h. The mixture was then concentrated under reduced pressure and the residue adjusted to pH = 8 with saturated NaHCO3 solution and extracted with ethyl acetate (3 ¡Á 150 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by basic preparative RP- HPLC method D to give 5-((7-(5-((5-fluoro-2′-isopropyl-[1,1′-biphenyl]-2- yl)oxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)methyl)-1H-benzo[d]imidazol- 2(3H)-one as a slight yellow solid. Yield: 7.2 g. LCMS method C: Rt = 0.663 min; (M+H)+ = 579.1.1H NMR (CD3OD): delta 8.13 (s, 1H), 7.58 (d, J = 6.8 Hz, 1H), 6.95-7.35 (m, 10H), 3.62 (s, 2H), 3.40-3.55 (m, 3H), 2.55-2.85 (m, 4H), 2.30-2.45 (m, 2H), 1.65- 1.85 (m, 4H), 1.00-1.10 (m, 6H).

The chemical industry reduces the impact on the environment during synthesis 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CACATIAN, Salvacion; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; MORALES-RAMOS, Angel; SINGH, Suresh, B.; VENKATRAMAN, Shankar; YUAN, Jing; ZHENG, Yajun; ZHUANG, Linghang; PARENT, Stephan, D.; HOUSTON, Travis, L.; (444 pag.)WO2017/214367; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8N2O

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 ¡Á 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3012-80-4.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53710-78-4, 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under ice-cooling, 1-(3-chloropropyl)-1H-imidazole (1.90 g, 13.14 mmol), cesium carbonate (4.28 g, 13.14 mmol) and a catalytic amount of potassium iodide were dissolved in DMF (30 mL).2-Fluoro-4-nitroaniline (1.38 g, 8.84 mmol) was added in one portion and the reaction was heated to reflux for 36 h.After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solvent was evaporated under reduced pressure. The residue was added to water (50 mL) and extracted with dichloromethane (20 mL ¡Á 2).The organic phase was washed with saturated brine (20 mL¡Á2), the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography (dichloromethane/methanol (V/V)=15/1).A yellow oil (2.85 g, 82%) was obtained.

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, 1-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 19225-92-4,Some common heterocyclic compound, 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, molecular formula is C5H7ClN2, 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.

The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for the starting material in Example 10), in DMF (6 ml). After stirring overnight at 40 C. the mixture was diluted with water and adjusted to pH7. After extraction with ethyl acetate, the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/methanol (98/2) as eluent to give 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (11 mg, 29%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6514971; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of (1-Methyl-1H-imidazol-4-yl)methanol

190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 % yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time).

The synthetic route of 17289-25-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem