Month: January 2021

Adding a certain compound to certain chemical reactions, such as: 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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 570-22-9, name: 1H-Imidazole-4,5-dicarboxylic acid

Thionyl chloride (94 ml; 1.29 mol) was added to a suspension of 1H-imidazole4;5- dicarboxylic acid (25 g; 157 mmol) in toluene (334 ml) and N;N-dimethylformamide (12.1 ml) and the mixture was stirred for 24 h at 80C. The mixture was concentrated under reduced pressure; 100 ml toluene were added and the mixture was concentrated under reduced pressure to give 35.5 g of the title compound as crude material; which was usedat the same day without further purification for subsequent steps.

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, 1H-Imidazole-4,5-dicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERSTAFF, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (136 pag.)WO2017/55313; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, molecular formula is C8H6N2O2, 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 3.5-((7-(5-(4-fluoro-2-(2-methoxybutan-2-yl)phenoxy)pyrimidin-4-yl)-2,7- diazaspiro[4.4]nonan-2-yl)methyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one (0935) To a solution of crude 2-(2-((4-(2,7-diazaspiro[4.4]nonan-2-yl)pyrimidin-5- yl)oxy)-5-fluorophenyl)butan-2-ol and 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5- carbaldehyde (Intermediate 40, 7 mg, 0.04 mmol) in MeOH (3 mL) was added NaBH3CN (8 mg, 0.13 mmol) at RT and the reaction mixture was stirred for 15 h. Evaporation of the solvent followed by purification by RP-HPLC method A afforded 5-((7-(5-(4-fluoro-2- (2-methoxybutan-2-yl)phenoxy)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)methyl)- 1,3-dihydro-2H-benzo[d]imidazol-2-one TFA salt. LCMS method G: Rt = 4.01 min; (M+H)+ = 547.62.1H NMR (CD3OD): delta 8.52 (bs, 1H), 7.65 (m, 1H), 7.34 (d, J = 9.6 Hz, 1H), 7.21-7.18 (m, 2H), 7.13-7.10 (m, 3H), 4.43 (s, 2H), 4.20-3.95 (m, 4H), 3.70-3.50 (m, 2H), 3.47-3.36 (m, 2H), 3.15 (s, 3H), 2.34-2.05 (m, 4H), 1.96-1.87 (m, 2H), 1.58 (s, 3H), 0.76 (t, J = 7.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, its application will become more common.

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

Synthetic Route of 29914-81-6, A common heterocyclic compound, 29914-81-6, name is 1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene, molecular formula is C20H14N4, 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.

c. Add 2.56 mmol of 1,14.3 mmol KOH and 2 mL of 1-iodo-n-hexane were dissolved in 30 mL of acetonitrile and refluxed for 24 hours. The solvent was removed to obtain a brown oil, which was dissolved in chloroform. Distilled water was extracted and washed 9-10 times, and the filtrate was taken to obtain a brown solution. Concentrated to 3 ~ 5mL, using 100 ~ 200 mesh silica gel as stationary phase, ethyl acetate was used as the eluent for column chromatography. The Rf of the product was 0.7 to 0.8. bisbenzimidazole phenyl complex 2 was obtained (yellow-white solid, yield 89%).

The synthetic route of 29914-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Yuxin Intelligent Science And Technology Institute Co., Ltd.; Xi Yanan; Hu Shujin; (17 pag.)CN110590853; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41384-83-2, name is 4-Nitro-1-phenyl-1H-imidazole, 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. Recommanded Product: 41384-83-2

To a solution of 4-nitro-l -phenyl- lH-imidazole (0.17 g, 0.89 mmol) in THF (5 ml) was added 10% Pd/C (0.1 g), at rt. The reaction mixture was purged with H2gas for 2 h at rt. The resulting reaction mixture was carefully filtered through celite hyflow and concentrated under reduced pressure to yield 1 -phenyl- lH-imidazol-4-amine, LCMS: Method C, 2.86 min, MS: ES+ 159.93.This material was directly used for the next step without further purification.

The synthetic route of 41384-83-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark Ian; WOODROW, Michael David; (63 pag.)WO2017/109488; (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. 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H7N3O2

Part A. Preparation of 1-(4-aminophenyl)imidazole. 1-(4-Nitrophenyl)imidazole (5.0 g) and 200 mL of methanol were combined to form a solution at ambient temperature. The addition of a catalytic amount of 10% palladium on carbon turned the solution into a suspension. Placement of the reaction mixture under a hydrogen atmosphere initiated the reduction. The reaction proceeded overnight (15h) at ambient temperature. Filtration through a celite pad separated out the catalyst. Concentration of -the filtrate under reduced pressure gave the title product as a pale yellow solid (3.99 g). 1H-NMR(DMSO d6) delta: 7.95 (s, 1H), 7.45 (s, 1H), 7.18 (d, 2H), 6.99 (s, 1H), 6.60 (d, 2H), 5.25 (s, 2H) ppm. LRMS(GC/MS) m/z 160 (M+H, 100).

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 2301-25-9.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP946508; (2009); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – 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. 693-98-1, name is 2-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Formula: C4H6N2

A mixture of l-fluoro-4-nitrobenzene (10 g, 70.9 mmol), 2-methyl-lH- imidazole (5.8 g, 70.9 mmol), and Cs2C03 (34.7 g, 106.4 mmol) in degassed DMF (200 mL) was heated at 100¡ãC under nitrogen overnight. When TLC indicated that l-fluoro-4-nitrobenzene was consumed, the reaction mixture was concentrated in vacuo. The residue was diluted with water (300 mL), and a grey precipitate was formed and was isolated to give 2-methyl-l-(4- nitrophenyl)-lH-imidazole (12.8 g, yield 89percent).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; WO2011/75478; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15965-31-8, 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. 15965-31-8, name is 5-Chloro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-chloro- 1 H-imidazole (5.0 g, 48.8 mmol), l-chloro-2-methoxy-4- nitrobenzene (9.15 g, 48.8 mmol), and potassium hydroxide flakes (2.74 g, 48.8 mmol) in anhydrous DMSO (50 mL) was heated at 80 0C for 20 h. The reaction mixture was allowed to cool to rt and was poured into 800 mL of water with vigorous stirring. The resulting yellow-orange precipitate was collected by vacuum filtration using a coarse sintered glass funnel. The crude wet solid was transferred to a 1 L Erlenmeyer flask. Absolute ethanol (250 mL) was added to the flask and the resulting suspension was heated until all of the solids dissolved. The clear solution was cooled to rt and the desired product slowly crystallized. After 2 h, the crystalline solid was collected by vacuum filtration and rinsed with 100 mL of fresh ethanol. The solid was dried under high vacuum to afford 4-chloro- l-(2-methoxy-4-nitrophenyl)-l H-imidazole (5.2 g, 42 % yield) as an off-white crystalline solid. LC-MS (M+H)+ = 254.0. 1H NMR (500 MHz, CDCl3) delta ppm 7.94 – 8.01 (m, 2 H) 7.76 (d, J=I.53 Hz, 1 H) 7.45 (d, J=8.55 Hz, 1 H) 7.21 (d, ./=1.53 Hz, 1 H) 4.02 (s, 3 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, 5-Chloro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, III, Lorin A.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2011/14535; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – 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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16681-56-4

To a microwave vial was added 6-(2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-5 dioxaborolan-2-yl)phenyi)-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine(Intermediate 9-3, 100 mg, 0.21 mmol), 2-bromo-1 H-imidazole (61.2 mg, 0.42 mmol), Na2C03 (44mg, 0.42 mmol), and Pd(PPh3)2CI2 (14 mg, 0.02 mmol), followed by DME (1 mL)/EtOH 0.25ml)/(H20 (0.25 ml). The vial was purged with N2 for 10 min and the reaction mixture was heated at150C in a microwave reactor for 20 min. The reaction mixture was filtered through celite and the10 filter cake was washed with EtOAc. The filtrate was concentrated in vacuo to give the crude productwhich was purified by silica gel chromatography (5%-15% MeOH/DCM) to afford 6-(4-(1 H-imidazol-2-yl)-2-methoxyphenyi)-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (40 mg,MS: 421.3 [M+H+]).

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHEUNG, Atwood; CHIN, Donovan Noel; DALES, Natalie; FAZAL, Aleem; HURLEY, Timothy Brian; KERRIGAN, John; O’BRIEN, Gary; SHU, Lei; SUN, Robert; SUNG, Moo; WO2014/28459; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 670-96-2, name is 2-Phenyl-1H-imidazole, 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. Computed Properties of C9H8N2

Into a 15mL pressure tube, sequentially add 1a (43.3mg, 0.3mmol), dichloromethane (3mL), 2h (68.5mg, 0.45mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3bb (58.3 mg, 66%) as a white solid.

The synthetic route of 2-Phenyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Normal University; Zhang Xinying; Zhang Linghua; Xu Yuanshuang; Fan Xuesen; (23 pag.)CN110372708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57531-37-0, 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 57531-37-0 as follows.

Example 4246To a stirred solution of compound 45 (0.7 mmol) in dry DMF is added K2CO3 (1.4 mmol) and NaI (0.066 mmol)and stirred for 30 min at rt. Then compound 2-chloro-4nitro-imidazol (0.84 mmol) is added at rt and stirred for over night at 80 0C and the reaction is monitored by TLC. The reaction mixture is diluted with water and extracted with DCM (3 x 25 mL) and washed with water, brine and dried (over with Na2SO4) and concentrated under vacuum. The crude compound is purified over neutral alumina using 30percent EtOAc/pet-ether as eluent to give 46. MS: M+ 396.3

According to the analysis of related databases, 57531-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; US DEPARTMENT OF HEALTH & HUMAN SERVICES; WO2007/75872; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem