Month: February 2021

Electric Literature of 20485-43-2, These common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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: : TBTU (0.90 g, 0.27 mmol) was added to a mixture of intermediate (G45) (0.1 g, 0.25 mmol) with 1 -methyl- lH-imidazole-2-carboxylic acid (0.40 g, 0.27 mmol) and DIEA (0.65 mL, 0.39 mmol) in DCM (5 mL). The reaction mixture was stirred at RT overnight. The reaction mixture was poured into water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated till dryness. The residue was purified by column chromatography (silica gel, DCM). The pure fractions were collected and the solvent was evaporated to give 97 mg (76%) of compound (El).

Statistics shows that 1-Methyl-1H-imidazole-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 20485-43-2.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; LANCOIS, David, Francis, Alain; GUILLEMONT, Jerome, Emile, Georges; RABOISSON, Pierre, Jean-Marie, Bernard; ROYMANS, Dirk, Andre, Emmy; ROGOVOY, Boris; BICHKO, Vadim; LARDEAU, Delphine, Yvonne, Raymonde; MICHAUT, Antoine, Benjamin; (326 pag.)WO2016/174079; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A 20 mL vial was charged with a 1.5 mL of ammonium acetate/acetic acid buffer solution (pH 4) in methanol. To this Example 87D (35.24 mg, 0.109 mmol) was added to form a suspension. lH-benzo[d]imidazole-2-carbaldehyde (23.89 mg, 1.5 eq, 0.164 mmol) and Si-BH3CN (from Silicycle, 0.88mmol/g loading, 371.49 mg) were then added. The vial was capped and placed to stir at 40¡ãC overnight. Upon completion, the crude mixture was filtered, concentrated, and purified by HPLC (see Example 360 for protocols) to provide the title compound as a trifluoroacetic acid salt. lH NMR (400 MHz, pyridine-d5) delta ppm 2.57 (q, J = 4.1, 3.2 Hz, 2H), 2.83 (t, J = 5.7 Hz, 2H), 3.39 (q, J = 2.8 Hz, 2H), 3.71 (s, 3H), 4.17 (s, 2H), 6.61 (s, 1H), 6.64 – 6.67 (m, 1H), 7.09 (dd, J = 9.1, 4.5 Hz, 1H), 7.26 (ddd, J = 9.1, 7.9, 3.2 Hz, 1H), 7.32 (d, J = 4.9 Hz, 1H), 7.34 – 7.39 (m, 2H), 7.49 (dd, J = 8.9, 3.2 Hz, 1H), 7.89 (dd, J = 6.0, 3.2 Hz, 2H), 8.58 (d, J = 5.0 Hz, 1H). MS (ESI+) m/z 454.2 (M+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, 1H-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 56248-10-3,Some common heterocyclic compound, 56248-10-3, name is 5-Phenyl-1H-imidazole-2-carbaldehyde, molecular formula is C10H8N2O, 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: To a stirred solution of compound 3 (100mg, 0.40 mmol) in ethanol was added corresponding benzohydrazides (4a-m) (1.0 mmol) and refluxed for 1 h. The reaction mass was washed with pet ether, filtered and dried undervacuum to obtain the pure hydrazone compounds. Yields ofthe products varied between 78 and 88 %.

The synthetic route of 56248-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Prasanna, V. Laxmi; Narender; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3605 – 3608;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1450-93-7, The chemical industry reduces the impact on the environment during synthesis 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), I believe this compound will play a more active role in future production and life.

To a stirred solution of 5-methylfuran-2-carbaldehyde (200 mg, 2 equiv.), 2- aminoimidazole hemisulfate (240.1 mg, 1 equiv.) and TEA (281 pL, 2.2 equiv.) in dichloromethane (6 mL) was added Ti(/PrO)4 (619.5 mg, 2.4 equiv.) and the mixture was stirred at room temperature for 16 hours. Volatiles were evaporated. The concentrated mixture was dissolved in MeOH (6 mL) and NaBH4 (172 mg, 5 equiv.) was added portionwise every 30 minutes until almost complete conversion to the wanted amine. The reaction mixture was transferred to a separatory funnel containing NaHCCf (15 mL), and extracted with DCM (2x 15 mL). The combined organic extracts were dried over Na2S04, were filtered, and the solvent was removed in vacuo to yield the crude product (222 mg). LCMS: MW (calcd): 177.20; MS (ES+, m/z)¡¤. 178.08 [M+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, 1H-imidazol-2-amine sulfate(2:1), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E-THERAPEUTICS PLC; POLJAK, Tanja; MODRIC, Marina; VADLAMUDI, Srinivasamurthy; STUBBERFIELD, Colin; (0 pag.)WO2019/229464; (2019); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

To 38.1 g (0.250 mol) 2-chlorobenzimidazole, 25.6 g 0.275 mol) aniline in 250 ml NMP 26.4 g (0.275 mmol) methane sulphonic acid is added. The reaction mixture is stirred at 100 C for 3 h under nitrogen. The reaction mixture is poured on a saturated solution of sodium hydrogen carbonate in water. The water phase is extracted with ethyl acetate. The organic phase is 3 times washed with water and the organic phase is dried with magnesium sulfate. The solvent is removed in vacuum. The product is decocted in 100 ml dichloromethane. Yield 43.6 g (83%) The above reaction is carried out according to a procedure given in US20090186879 (page 57). 1H NMR (400 MHz, DMSO-d6): delta = 10.9 (s, 1 H), 9.38 (s, 1 H), 7.29-7.36 (d, 2H), 2.29-7.36 (m, 4H), 6.96-7.02(m, 2H), 6.91 -6.94 (m, 1 H).

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; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; NAGASHIMA, Hideaki; (314 pag.)WO2017/56052; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-88-1,Some common heterocyclic compound, 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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.

EXAMPLE 93B (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (4-cyanophenyl)(hydroxy)(1-methyl-1H-imidazol-5-yl)acetate A mixture of zinc dust (9.4 g, 143.7 mmol) in THF (5 mL) was treated with 1,2-dibromoethane (0.62 mL, 7.2 mmol), heated to 50 C., stirred for 15 minutes, and cooled to 30 C. The mixture was treated with chlorotrimethylsilane (0.91 mL, 7.2 mmol), stirred for 5 minutes, heated to reflux, treated slowly with 5-iodo-1-methyl-1H-imidazole (20.0 g, 96.2 mmol), and continued to reflux for 30 minutes. The reaction was cooled to room temperature and stirring was aborted to allow the excess zinc to settle to the bottom of the flask. A solution of magnesium bromide diethyl etherate (10.3 g, 39.9 mmol) and Example 93A (50.0 g, 79.8 mmol) in THF (100 mL) was cooled to -10 C. and treated with a solution of the 1-methyl-5-zinciodo-1H-imidazole from above in THF (120 mL) over 15 minutes. The mixture was warmed to room temperature, stirred for 18 hours, quenched with saturated NH4Cl (100 mL), and the layers were separated. The aqueous phase was extracted with ethyl acetate (300 mL) and the combined organic phases were washed with brine. The reaction mixture was filtered through diatomaceous earth (Celite), treated with toluene (~250 mL), concentrated at a bath temperture of 60 C. The mixture was allowed to sit for 18 hours and then filtered. The filter cake was washed with toluene and dried under vacuum at 50 C. to provide 30.0 g (81% potent, 77% yield, 97.4% de). MS (ACPI) m/e 396 (M+H)+; 1H NMR (CD3OD) delta8.02 (br s, 1H), 7.78 (d, 2H), 7.63 (d, 2H), 7.13 (br s, 1H), 4.76 (ddd, 1H), 3.49 (s, 3H), 2.06 (br d, 1H), 1.72-1.60 (m, 2H), 1.55-1.42 (m, 1H), 1.30 (m, 1H), 1.14 (q, 1H), 1.07-0.98 (m, 2H), 0.95 (d, 3H), 0.94-0.84 (m, 1H), 0.66 (d, 3H), 0.50 (d, 3H).

The synthetic route of 71759-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2003/87940; (2003); 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 1179361-84-2 as follows. Formula: C6H9N3O2

Synthesis of Compound 8.2. Into a 100-mL sealed tube, was placed 8.1 (475 mg, 3.06 mmol, 1.00 equiv), ammonia in methanol (50 mL). The resulting solution was stirred for 48 h at 70 C. The resulting mixture was concentrated in vacuo. This resulted in 350 mg (91%) of l-amino-lH-imidazole-5-carboxamide (8.2) as an off-white solid.

According to the analysis of related databases, 1179361-84-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; (102 pag.)WO2017/4134; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 25676-75-9,Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

[00288] A mixture of5-(4-methylpiperazin-1-ylmethyl)-furan-2-carboxylic acid [8- (4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl]-amide (98 mg, 0.18 mmol, 1.0 eq), 4-bromo-1 -methyl-1H-imidazole (63 mg, 0.39 mmol, 2.2 eq.) Pd(PPh3)4 (21 mg, 0.017 mmol, 0.1eq), K2CO3 (49 mg, 2.0 eq) in 9:1 dioxane:H20 (5ml_) was purged with N2 for 15 min and the mixture was heated to 110 C for 1 h. The reaction mixture was concentrated under reduced pressure and the residue dissolved in MeOH and loaded onto a SCX-2 cartridge. The cartridge was washed with MeOH, and the compound eluted using 0.5M ammonia in methanol. The product-containing fractions were concentrated under reduced pressure to yield the crude material which was purified by prep HPLC to give 5-(4- methyl-piperazin-1-ylmethyl)-furan-2-carboxylic acid [8-(1 -methyl-1H-imidazol-4-yl)-2,3- dihydro-benzo[1,4]dioxin-2-ylmethyl]-amide (13.3 mg, 16.4 %) as an off-white solid AnalpH9_MeOH_QC_V1 : Rt: 6.93 min, m/z 452.4 [M+H]+ 1H NMR (400MHz, DMSO-d6): d 8.65 (t, J = 6.0Hz, 1H) 7.62-7.57 (m, 3H) 7.13 (d, J = 3.5 Hz, 1H) 6.82 (t, J = 7.3 Hz, 1H) 6.70 (dd, J = 7.8, 1.5 Hz, 1H) 6.46 (d, J = 3.3 Hz, 1H) 4.42-4.35 (m, 2H) 3.97 (dd, J = 1 1.9, 8.6 Hz, 2H) 3.77-3.68 (m, 1H) 3.56 (s, 3H) 3.51 (s, 2H) 2.48-2.20 (m, 8H) 2.16 (s, 3H)

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54624-57-6, name is 2-Bromobenzimidazole, 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 54624-57-6, category: imidazoles-derivatives

2-bromobenzoimidazole 100mmol, nitrogen eight membered (or sulfur) heterocyclic boride intermediate 220mmol were added to a 1L three-necked flask, was dissolved in 400mL of toluene, was added under nitrogen tetrakistriphenylphosphine palladium 1.5mmol, 250mmol potassium carbonate, distilled water 100mL, the reaction was stirred at reflux for 24 hours, cooled to room temperature, after the reaction liquid separation, silica gel funnel, washing, spin-dry, recrystallized, filtered, 65mmol obtain compound 8 as a white solid, yield 65percent.

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, 2-Bromobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jilin Optical and Electronic Materials Co., Ltd.; Ma, Xiaoyu; Song, Qiaohong; Zhao, He; (22 pag.)CN105315229; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1072-62-4, The chemical industry reduces the impact on the environment during synthesis 1072-62-4, name is 2-Ethyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: The synthetic route is shown in Scheme 2. For example, to a stirred solution of compound 2 (506mg, 83 1 mmol) in 30 mL acetonitrile were added anhydrous K2CO3 (275 mg, 2mmol) and imidazole (204mg, 3mmol) at 25. Then the mixture was stirred at 25 for 24 h. The reaction mixture was filtered, and the 85 filtrate was evaporated under reduced pressure. The residue was treated with water (50 mL) and extracted 86 with dichloromethane (4¡Á30 mL). The organic layer was combined, dried with anhydrous Na2SO4, and 87 concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography 88 with chloroform/methanol (5:1) as eluent to give compounds 6-24 as solid.compound 6. 4?-(3-Imidazole-propoxy)-arctigenin. Yeild 83.33%.

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, 2-Ethyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Yang; Liu, Lei; Li, Boyang; Shen, Yufeng; Wang, Gao-Xue; Zhu, Bin; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 183 – 194;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem