Category: imidazoles-derivatives

Electric Literature of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-62-4,Some common heterocyclic compound, 1072-62-4, name is 2-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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: (bromomethyl)-5-fluorophenyl)(2-fluoro-4,5-dimethoxyphenyl)methanone 4 (0.25 g, 0.68 mmol, 1.0 equiv) and 4-hydroxyl piperidine (150 muL, 1.35 mmol, 2.0 equiv) weredissolved in anhydrous dichloromethane (10 mL) and dryK2CO3 (100 mg, 0.72 mmol, 1.1 equiv) was added, and thenthe mixture was stirred at room temperature for 12 h. Thesolvent was removed by rotary evaporation and the residuewas purified by flash column chromatography over silica gelwith the system (14% ethyl acetate/petroleum ether, adding1.4% ammonia water) to obtain compound (5-fluoro-2-((4-hydroxypiperidin-1-yl)methyl)phenyl) 2-fluoro-4,5-dimethoxyphenyl)methanone 5a (0.2 g, 77%) as a yellow solid.The intermediates 5b-5g, 7a-7k, 9a-9g, 11a-11b wereprepared in a similar manner

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Xiu E; Kong, De Peng; Ban, Shu Rong; Ge, Rui; Li, Qing Shan; Medicinal Chemistry Research; vol. 28; 8; (2019); p. 1319 – 1337;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

To a solution of 1-isopropenylbenzimidazolone (220 mg, 1.3 mmol) in dry THF (10 inL) are added triphenylphosphine (397 mg, 1.5 mmol) and (l,2-Dimethyl-lH-indol-7-yl)-methanol (220 mg, 1.3 mmol). Then diisopropyl azodicarboxylate (0.31 mL, 1.5 mmol) is added drop wise into the above solution at room temperature. The mixture is stirred for 16 hrs and then the solvent is removed under vacuum. The residue is purified by flash column chromatography using 10-30% EtOAc in hexanes to give 200 mg (48%) of l-(l,2-dimethyl-lH-indol-7-ylmethyl)-3- isopropenyl-l,3-dihydro-benzimidazol-2-one.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-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. name: 2-Methyl-4-(trifluoromethyl)-1H-imidazole

Example 57 Preparation of N-(2,6-difluorobenzyl)-5-(2-methyl-4-(trifluoromethyl)-1H-imidazol-1-yl)pyridin-2-amine (106) A suspension of 2-methyl-4-(trifluoromethyl)imidazole (300 mg, 2 mmol) and potassium carbonate (828 mg, 3 eq) in 4 mL DMSO was heated at 120 C. for 30 min before addition of 5-bromo-2-nitropyridine (406 mg, 2 mmol). The resulting suspension was heated at 120 C. for 4 more hours. After cooling down, the reaction mixture was worked up with EA/brine. Flash silica gel column purification furnished nitropyridine intermediate 103 (125 mg, yield 23%, purity>90%) as a light yellow solid.

The synthetic route of 33468-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CalciMedica, Inc.; US2012/316182; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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 39070-14-9, Application In Synthesis of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

To a suspension of N,N’-bis(2-bromoethyl)phosphorodiamidic acid (50mg, 0.16mmol), 1-methyl-2-nitroimidazole-5-methanol (50mg, 0.32mmol), and PPh3 (84mg, 0.32mmol) in THF (15mL) was added DIAD (0.13mL, 0.32mmol) at 0C. After the addition of DIAD, the reaction mixture was warmed to room temperature and stirred overnight. The solvent was removed, and the residue was purified by column chromatography on silica gel (DCM: MeOH=50:1) to afford compound 14 (37mg, 51%) as yellow gum. 1H NMR (400MHz, DMSO) delta 7.25 (s, 1H), 5.05-4.99 (m, 2H), 4.98 (d, J=7.6Hz, 2H), 3.94 (s, 3H), 3.42 (t, J=6.9Hz, 4H), 3.17-3.05 (m, 4H). 13C NMR (101MHz, DMSO) delta 146.1, 134.1(d, J=8.0Hz), 128.2, 55.7 (d, J=4.3Hz), 42.7, 34.3, 34.1 (d, J=5.0Hz). HRMS (ESI): m/z Calcd for C9H17Br2N5O4P, [M+H]+: 469.9204, found: 469.9186.

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-Methyl-2-nitro-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Chen; Zhang, Qiumeng; Lu, Wei; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 135 – 141;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 85692-37-1, name is 1-(1-Methyl-1H-imidazol-2-yl)ethanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-(1-Methyl-1H-imidazol-2-yl)ethanone

2c: 1 -Methyl-2-acetylimidazole (1.8 g, 16.36 mmol) and LiOH (392 mg, 16.36 mmol) were stirred in MeOH (100 mL) before methyl 4-formylbenzoate (2.6 g, 16.36 mmol) was added. After 30 min a thick yellow precipitate was formed. The precipitate was filtered and dried under vacuum to yield 2c as a yellow solid (63%).

The synthetic route of 85692-37-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; JANDA, Kim, D.; (0 pag.)WO2020/14144; (2020); 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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methyl-1H-imidazole-4-sulfonyl chloride

Intermediate example 1-84 (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl l-methyl-lH-imidazole-4- sulfonateTo a solution of (35)-3-(dibenzylamino)chroman-5-ol (300 mg, 0.87 mmol, described in WO9914212A1) in acetonitrile (10 mL) was triethylamine (0.363 mL, 2.61 mmol) and 1- methyl-leta-imidazole-4-sulfonyl chloride (173 mg, 0.96 mmol) added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was concentrated in vacuo and purified by column chromatography using a gradient of ethyl acetate in heptane to yield 375 mg (88 %); 1H NMR (400 MHz, DMSO-J6) delta ppm 8.06 (d, 1 H), 7.93 (d, 1 H), 7.30 – 7.42 (m, 8 H), 7.18 – 7.27 (m, 2 H), 7.06 (t, 1 H), 6.69 (dd, 1 H), 6.62 (dd, 1 H), 4.17 – 4.31 (m, 1 H), 3.97 (t, 1 H), 3.61 – 3.73 (m, 7 H), 2.84 – 2.99 (m, 2 H), 2.63 – 2.75 (m, 1 H); MS (ESI) m/z 490 [M+H+].

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 137049-00-4.

Reference:
Patent; ASTRAZENECA AB; WO2008/130319; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3, 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 641571-13-3 as follows.

To a solution of 4-methyl-N3-[l-(7Eta-rhoyrrolo[2,3-J]pyrimidin-4-yl)-lEta- imidazol-2-yl] -benzene- 1,3 -diamine (15.0 mg, 0.049 mmol), 3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-benzoic acid (16.0 mg, 0.059 mmol), and DIEA (35yL, 0.20 mmol) in DMF (2mL) is added HATU (21 mg, 0.055 mmol). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (ImL). The resulting solution is subjected to purification by reverse-phase HPLC to give 3-(4-methyl- EPO imidazol-l-yl)-N-{4-methyl-3-[l-(7H-pyrrolo[2,3-cT]pyrimidm-4-yl)-lH-imidazol-2- ylamino]-phenyl}-5-trifluoromethyI-benzamide: 1H NuMR 600 MHz (DMSO-J6) delta 12.73 (s, IH), 11.32 0, IH), 10.67 (s, 1 H), 9.60 (s, 1 H), 8.82 0,1 H), 8.64-8.56 (m, 2H), 8.46 (s, IH), 8.43 (s, IH), 8.17 (s, IH), 7.93 (d, IH, J= 2.8 Hz), 7.79 (t, IH, J= 3.2 Hz), 7.52 (d, IH, J= 8.0 Hz), 7.30 (J, IH, J= 8.0 Hz), 7.11 (s, IH), 7.07 (m, IH), 2.39 (s, 3H), 2.36 (5, 3H); MS m/z 558.2 (M + 1).

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2006/101783; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature 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.

To a suspension of 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

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; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); 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. 162356-38-9, name is 2-(2-Bromophenyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Bromophenyl)-1H-imidazole

Step K 1-(4-Toluenesulfonyl)-2-(2-bromophenyl) imidazole A solution of 2.50 g (11.6 mmol) of 2-(2-bromophenyl)imidazole in 10 mL of methylene chloride was treated with 1.9 mL of triethylamine (13.8 mmol), 2.64 g (13.8 mmol) of p-toluenesulfonyl chloride and 100 mg of 4-dimethylaminopyridine. The reaction mixture was stirred at room temperature for 15 minutes then transferred to a separatory funnel and washed with water, 5percent aqueous citric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and solvents removed under vacuum. The crude product was chromatographed on silica, eluding with hexane/ethyl acetate (1:1), to give 4.16 g (11.0 mmol 95percent) of the product which was recrystallized from hexane. FAB-MS: calculated for C16 H13 BrN2 O2 S 376,378; found 377,379 (M+H, 50percent). 1 H NMR (200 MHz, CDCl3): 2.32 (s, 3H), 7.09 (d, 2 Hz, 1H), 7.12 (d, 8 Hz, 2H), 7.28 (m, 5H), 7.46 (m, 1H), 7.57 (d, 2 Hz, 1H).

The synthetic route of 162356-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5583130; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem