Category: imidazoles-derivatives

Electric Literature of 288-32-4, The chemical industry reduces the impact on the environment during synthesis 288-32-4, name is 1H-Imidazole, I believe this compound will play a more active role in future production and life.

General procedure: In a flame-driedvessel, equipped with a magnetic stirrer, under argon atmosphere,were added 0.3 mL of anhydrous acetonitrile, the nucleophile (imidazoleor benzimidazole – 0.75 mmol, 1.5 eq.), the electrophile(alkyl or aryl iodide – 0.5 mmol, 1 eq.), the base (1 mmol, 2 eq.),and the copper catalyst (0.05 mmol – 10% loading). The reactionvessel was heated to 80 C and left under stirring for 24 h. Thereaction mixture was then allowed to cool to room temperature,diluted with dichloromethane (5 mL) and filtered through celite. The celitepad was further washed with dichloromethane(2 x 5 mL). The combined organic phases were washed with water(2 x 5 mL) and brine (2 x 5 mL). The organic solvents were thenremoved in vacuo to yield the crude product, which was purifiedby flash column chromatography on silica gel using a gradient mixtureof ethyl acetate/petroleum ether as eluent. The 1H and 13CNMR spectral data for all N-arylatedimidazoles and benzimidazolesare in full agreement with those reported to literature [57-61].

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, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Milenkovi?, Milica R.; Papastavrou, Argyro T.; Radanovi?, Du?anka; Pevec, Andrej; Jagli?i?, Zvonko; Zlatar, Matija; Gruden, Maja; Vougioukalakis, Georgios C.; Turel, Iztok; An?elkovi?, Katarina; ?obelji?, Bo?idar; Polyhedron; vol. 165; (2019); p. 22 – 30;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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 6775-40-2, COA of Formula: C9H9N3

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

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:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5805-57-2, The chemical industry reduces the impact on the environment during synthesis 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, I believe this compound will play a more active role in future production and life.

A mixture of 241 (97 mg, 0.25 mmol), (1H-benzimidazol-2-yl)methanamine3 (108 mg, 0.737 mmol), NaBH(OAc)3 (58 mg, 0.27 mmol), and MS4A (80 mg) in CH2Cl2 (8.2 mL) was stirred at room temperature for 10 h. After addition of MeOH, the reaction mixture was partitioned between AcOEt and sat. aq. NaHCO3. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by NH silica gel column chromatography (hexane/CH2Cl2, 1:1-0:1) to give the corresponding amine as pale red oil. To a solution of the amine in EtOH (1.0 mL) was added aq. HCl (2 M, 2.0 mL) and the mixture was heated under reflux for 4 h. The solvent was evaporated, and the residue was partitioned between CH2Cl2 and aq. HCl (1 M). The aqueous layer was basified with aq. NaOH and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (CHCl3/MeOH, 99:1) to give 13 as a free amine. The amine was dissolved in methanolic HCl (2 M) and the solvent was evaporated. The residue was triturated with Et2O to give 13?3HCl (45 mg, 0.12 mmol, 47% for 2 steps) as a pale-brown amorphous solid. 1H NMR (500 MHz, CD3OD) delta 8.76 (1 H, s, imidazole-2), 7.89 (2 H, dd, J = 6.3, 2.9 Hz, aromatic), 7.65 (2 H, dd, J = 6.3, 2.9 Hz, aromatic), 7.32 (1 H, s, imidazole-5), 4.89 (2 H, s, -NCH2Ar), 3.49 (2 H, brs, -CH2CH2N-), 2.04-1.85 (3 H, m, H-1, -CH2CH2N-), 1.34 (1 H, brs, H-2), 1.13 (1 H, brs, H-3a), 1.08 (1 H, brs, H-3b); 13C NMR (125 MHz, CD3OD) delta 144.36, 136.72, 134.40, 133.25, 128.17, 115.99, 115.68, 49.85, 42.96, 30.98, 19.43, 14.37, 13.33; HRMS (EI) calcd for C16H20N5 282.1713, found 282.1715 [(M + H)+]; Anal. Calcd for C16H19N5?3HCl?1H2O: C, 47.02; H, 5.92; N, 17.13. Found: C, 47.15; H, 5.91; N, 17.05.

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]imidazol-2-yl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Watanabe, Mizuki; Kobayashi, Takaaki; Ito, Yoshihiko; Fukuda, Hayato; Yamada, Shizuo; Arisawa, Mitsuhiro; Shuto, Satoshi; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3630 – 3633;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

623577-60-6, name is 4-Bromo-1-isopropyl-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. category: imidazoles-derivatives

A mixture of methyl 5-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2- carboxylate (300 mg, 1.08 mmol), 4-bromo-l -(propan-2 -yl)-lH-imidazole (307.0 mg, 1.62 mmol), Pd(PPh3)4 (250.2 mg, 0.22 mmol), K2CO3 (448.8 mg, 3.25 mmol) in dioxane (5 ml) was stirred at 100 C under nitrogen atmosphere overnight. The resulting mixture was 39 concentrated under vacuum and purified by reverse phase flash chromatography with 0-37% MeCN/fhO to afford compound 23-a (180 mg, 64.12%) as yellow oil.

The synthetic route of 623577-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WANG, Guoqiang; SHEN, Ruichao; GRANGER, Brett; HE, Jing; XING, Xuechao; HE, Yong; LONG, Jiang; MA, Jun; WANG, Bin; OR, Yat, Sun; (99 pag.)WO2019/213244; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirring solution of 1H-imidazole-4-carbaldehyde (2.00 g, 20.81 mmol) in THF (20 mL) was added DMAP (0.64 g, 5.20 mmol) and TEA (5.80 ml, 41.60 mmol) followed by Boc-anhydride (5.80 mL, 24.98 mmol) and the resulting reaction mixture was stirred as ambient temperature for 18 h. The reaction mixture was concentrated to dryness under reduced pressure and diluted with water (50 mL). The solid precipitate was filtered and dried under vacuum to obtain Intermediate 130A (2.50 g, 49.00%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) G ppm 1.59 (s, 9 H), 8.37-8.39 ( d, J = 5.40 Hz, 2 H), 9.80 (s., 1 H). LCMS (Method-O): retention time 1.00 min, [M-56] 141.2.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

Synthesis of tert-butyi 4-(4-carbamoyl-4-(methylamino)piperidin-1~yl)~ 3-( 1 H-imidazote-2-carboxamido)phenylcarbamate (lnt-14b)A mixture of 1 H-imidazole-2-carboxylic acid (19 mg, 0.17 mmol), aniline lnt-14b (60 mg, 0.17 mmol), HATU (69 mg, 0.18 mmol), diisopropyiethylamine (57 pL, 0.33 mmol) was stirred in N,N-dimethylformamide (2 mL). Water and ethyl acetate were added, and the layers were separated. The separated organic layer was washed with water. The separated organic layer was dried ( gS04) and filtered. The solvents were removed in vacuo and chromatographic purification (ethyl acetate – hexane) of the residue gave amide lnt-14c (26 mg, 35%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Imidazolecarboxylic acid, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang; WO2011/149874; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36947-68-9, name is 2-Isopropyl-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 36947-68-9, Computed Properties of C6H10N2

A mixture of 2-bromo-N-tert-butyl-6-(4-chlorophenyl)-pyridine-4-carboxamide (intermediate 2) (91.9 mg, 250 mupiiotaomicron), commercially available 2-isopropyl-lH-imidazole (55.1 mg, 500 mupiiotaomicron) and potassium carbonate (69.1 mg, 500 mupiiotaomicron) in DMSO (1.5 ml) was purged with argon in an ultrasonic bath for 5 min, N,N-dimethylglycine (10.3 mg, 100 mupiiotaomicron) and copper(I)iodide (9.52 mg, 50 mupiiotaomicron) were added, the tube sealed and heated for 17h at 115C. The reaction mixture was diluted with water (10 ml), the precipitate collected by filtration and further purified by flash chromatography on silica gel [heptane/ethyl acetate (50-100%)] to yield the title compound (50 mg, 50%) as an off-white foam, MS (ISN) m/z = 397.3 [(M+H)+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Isopropyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HOENER, Marius; WICHMANN, Juergen; (65 pag.)WO2017/9274; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5395-50-6, 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. 5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1 ,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-dione (1.99 g, 7.6 mmol) in 1.5 ml of DM50 was dissolved. Then, 0.3 ml nitric acid (65%) and 4-ethylcyclohexanol (10.5 ml, 75.9 mmol) were added to the solution and the mixture was heated at 60 C. for 16 hours. After the reaction was over, the reaction liquid was cooled and iN NaOH was added around pH 7. Around 100 ml ethyl acetate was used to extract with mixture and the organic phase was washed by saturated NaC1(aq) solution for 2 times. Afier being dried by Na2SO4, the solvent was removed

The synthetic route of 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Rohm and Haas Electronic Materials Korea Ltd.; Grandbois, Matthew; Kim, Myung Yeol; Ryu, Eui Hyun; Sim, Jae Hwan; Jang, Min Kyung; Lee, Jung-June; (17 pag.)US2017/59991; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 13750-62-4, These common heterocyclic compound, 13750-62-4, name is 1-Benzyl-2-methyl-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.

[1-BENZYL-2-METHYL-1H IMIDAZOLE] (50 mg, 0.3 mmol) and 3,4-dichlorobenzyl bromide (77 mg, 0.32 mmol) in 0.2 ml acetonitrile (a few drops of DMF were added for solubility) were stirred overnight at room temperature. The mixture was diluted with ether, the solid filtered, washed with ether and dried to give 112 mg of product. LC/MS (ES+) m/e 333 [[M+1]]

The synthetic route of 13750-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/101970; (2003); 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: Equimolar quantities of 1-methyl-1H-benzo[d]imidazole-2-carbaldehyde and the respective aniline derivative were placed in microwave vial, and the reaction mixture was irradiated at 90?C during 4?min. After cooling to room temperature, the resulting residue was then purified by recrystallization in ethanol to give the pure Schiff base. N-(4-methoxyphenyl)-1-(1-methyl-1H-benzo[d]imidazol-2-yl)methanimine (L1).

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; Boulebd, Houssem; Lahneche, Yousra Doria; Khodja, Imene Amine; Benslimane, Meriem; Belfaitah, Ali; Journal of Molecular Structure; vol. 1196; (2019); p. 58 – 65;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem