Category: imidazoles-derivatives

Application of 492-98-8, These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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.

Example 4: Synthesis of (tetrakis(2-(2,4-difluorophenyl)pyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(dfppy)2BIm]2) [0243] [0244] Under argon atmosphere, into a 250 mL Schlenk flask equipped with a stirrer were placed 486 mg (0.40 mmol) of di-mu-chloro-tetrakis(2-(2,4-difluorophenyl)pyridinato) diiridium(III), 54 mg (0.40 mmol) of 2,2′-biimidazole and 80 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 1 hour. Subsequently, 111 mg (0.84 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 2 hours. After the completion of the reaction, the reaction liquid was concentrated, and then methylene chloride, water and a saturated aqueous solution of ammonium chloride were added to the resultant concentrate until pH became 7, and the organic phase was separated from the water phase. The resultant organic phase was dried with sodium sulfate, and filtered, and then the filtrate was concentrated. And then, the resultant concentrate was washed with hexane, to provide 441 mg of binuclear iridium complex (1) as a yellow solid. (Isolation yield: 86 %) [0245] The obtained binuclear iridium complex (1) was a mixture of two different types of isomers, and the abundance ratio was 60:40. The binuclear iridium complex obtained as the main product (60 %) was referred to as “binuclear iridium complex (1a)” and the binuclear iridium complex obtained as the secondary product (40 %) was referred to as “binuclear iridium complex (1b)” [0246] Additionally, the binuclear iridium complex (1) was a novel compound, which had the following properties: [0247] 1H-NMR (400MHz, C4D8O, delta (ppm)); Binuclear iridium complex (1a); 8.17 (d, 4H), 8.13-8.12 (m, 4H), 7.79-7.75 (m, 4H), 7.91-7.15 (m, 4H), 6.49-6.42 (m, 4H), 6.22 (s, 4H), 5.84-5.81 (m, 4H) Binuclear iridium complex (1b); 8.24 (d, 4H), 7.85-7.81 (m, 4H), 7.74-7.72 (m, 4H), 6.95-6.91 (m, 4H), 6.49-6.42 (m, 4H), 6.24 (s, 4H), 5.77-5.74 (m, 4H) FD-MS (M/Z): 1276 (M+)

Statistics shows that 1H,1’H-2,2′-Biimidazole is playing an increasingly important role. we look forward to future research findings about 492-98-8.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2466-76-4, The chemical industry reduces the impact on the environment during synthesis 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, I believe this compound will play a more active role in future production and life.

Step Three; N-((1S, 2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6- hydroxy-3, 4-dihydro-2H-chromen-4-yl] amino} propyl) acetamide; OH H H OH H H2N N N-N 2HCl \ 1. 2 equiv. acetylimidazole 2HCl ~ + l 1. 2equiv. acetinidazole 11 41 A 2. K2CO3, MeOH, H20/==\ F HOpercent F HO/ F F To a solution of the product from step 2 (200 mg, 0.43 mmol) in methylene chloride (5 mL) was added triethylamine (217 mg, 2.15 mmol) followed by 1-acetylimidazole (95 mg, 0.86 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and water (3 mL) and treated with potassium carbonate (300 mg, 2.17 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was acidified with 1N hydrochloric acid and extracted with ethyl acetate (3 x 50 mL). The combined extracts were washed with saturated sodium chloride, and dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-5percent methanol/methylene chloride provided the desired product (85 mg, 49percent) as a white foam.

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-(1H-Imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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 mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 3.59 g (9.8 mmol) of 1-octadecyl bromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 3.00 g (69%). Mp=56-58 C. IR-spectrum (KBr), cm-1: 3325, 3140, 3080, 2915, 2850, 1565, 1472,1378, 1165,1071, 871, 721. 1H NMR spectrum, 400 MHz (CDCl3), delta,ppm, J/Hz: 0.87 t (3H, J=7.0), 1.24-1.32m (30 H), 1.89-1.92m (2 H),3.98 t (2H, J=4.27), 4.26 t (2H, J=7.6), 4.53 t (2H, J=4.90), 7.31 s(1 H), 7.63 s (1 H), 9.73 s (1 H). ESI MS, m/z: 365.5 [M-Br]+.Calculated, %: C23H45 N2 OBr: C 62.00; H 10.18; N 6.29; Br 17.93;found, %: C 61.75; H 10.43; N 6.22; Br 17.58.

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
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. 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1243204-92-3

Example B3 a) Preparation of compound 4 A mixture of intermediate 1 (443 mg, 2.08 mmol), 4-fluorobenzoic acid hydrazide (320 mg, 2.08 mmol) and K2CO3 (143 mg, 1.04 mmol) in n-BuOH (15 ml) was heated in the microwave at 120 0C for 12 h. The solvent was removed under reduced pressure and the resulting residue partitioned between EtOAc/H2O. The phases were separated. The aq. phase was extracted with EtOAc, and the combined organic extracts were washed with brine and dried (MgSO^. Filtration and concentration under reduced pressure gave the crude product which was purified by column chromatography over silica gel (eluent: 100:0 to 90: 10 DCM/MeOH, gradient elution). The product fractions were collected and evaporated to yield 450 mg of compound 4 (62.0 %).

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 1243204-92-3.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. Product Details of 75370-65-9

Preparation of 1-(4-(dimethylamino)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea 4-(aminomethyl)-N,N-dimethylbenzenamine 2i (1 g, 6.9 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (2 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (1 g, 6.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 350 mg of a white solid. Yield = 16% 1HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.18 (2H, d, J = 5.6 Hz), 6.58 (2H, m), 6.69 (2H, d, J = 8.8 Hz), 6.86 (2H, m), 7.14 (2H, d, J = 8.8 Hz), 8.18 (1H, s), 9.98 (1H, bs), 10.58 (1H, bs); [M+1] 326.5 (C17H19N5O2 requires 325.37).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5, name: 1H-Benzo[d]imidazole-2-carbaldehyde

Example 5 3-(1H-benzimidazol-2-methylene)-5-(2-methylphenylaminosulfo)-2-indolone (Indo 5) 0.15 g (0.5 mmol) 5-(2-methylphenylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazol-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.12 g pale yellow solid, with a yield of 55.8percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta (ppm): delta13.82 (s, 1H), 11.70 (s, 1H), 9.44 (s, 1H), 8.20 (s, 1H), 8.00 (s, 1H), 7.82 (d, 1H, J=8.0 Hz), 7.78 (d, 1H, J=8.0 Hz), 7.61 (dd, 1H, J=16.8 Hz), 7.38 (t, 1H), 7.30 (t, 1H), 7.00-7.15 (m, 5H), 2.09 (s, 3H). ESI-MS m/z: 429 [M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(2-methylphenylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is 2-methylphenylaminosulfo, and R2 is hydrogen.

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; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 614-97-1, 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 614-97-1 as follows.

a 4-Iodo-5-methyl-1H-benzoimidazole A solution of 5-methyl-1H-benzoimidazole (132 mg, 1.0 mmol) and NIS (248 mg, 1.10 mmol) in 1 mL of TFA was reflux for 1 hr and then cooled to RT. Treated with 30 mL of EtOAc, the mixture was neutralized with sat. NaHCO3 solution. The organic layer was washed with H2O (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5% MeOH/CH2Cl2) gave 78 (30%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) delta 8.07 (d, 1H), 7.57 (br s, 1H), 7.22 (d, 1H, J=8.4 Hz), 2.59 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C8H7IN2, 259.0 (M+H), found 259.2.

According to the analysis of related databases, 614-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Computed Properties of C4H4N2O2

Example 130 (3.2 mg, 5.4 imol), 1H-imidazole-2-carboxylic acid (9.1 mg, 0.082 mmol) and DIEA (4.8 pi, 0.027 mmol) were dissolved in DMF (0.5 mL). HATU (2.07 mg, 5.44 imol) was added, and the reaction mixture was allowed to stir at rt for 2 h.The reaction mixture was concentrated, and the residue was purified by RP HPLC to provide the product (2.2 mg, 58%) as a clear glass (bis TFA salt). MS(ESI) m/z 455.3 (M+H)t ?HNMR(SOOMHz, CD3CN) oe 7.92(s, 1H), 7.87 (s, 1H), 7.57 (s, 2H), 7.17 (m, 3H), 6.80 (t, J=0.96 Hz, 1H), 5.45 (s, 2H), 4.65-4.92 (m, 2H), 4.29 (s, 2H), 3.65-3.99 (m,2H), 2.96 (t, J=5.91 Hz, 2H). Analytical HPLC: RT = 3.34 mm (Method A).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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. SDS of cas: 152628-02-9

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2403-66-9, 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. 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl Iodide (839muL, 13.48 mmol) was added to a mixture of the 3-(lH-benzimidazol- 2-yl)propan-l-ol (2.5g, 14.19 mmol) and Et3N (2.16mL, 15.6 mmol) in DCM (100 mL) at O0C. The reaction stirred for 40 minutes, was warmed to room temperature and stirred 1 hour. DMF (50 mL) was added and continued stirring for 1 hour. Cesium carbonate (4.62g, 14.19 mmol) and methyl iodide (839muL, 13.48 mmol) were added and the reaction stirred overnight. The reaction was diluted with EtOAc, washed with water, saturated sodium bicarbonate and brine. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude solids were triturated with ethyl ether/hexane (1 :2) to give the title compound (1-21: step 1) as a solid. Data for 1-21: step 1: ESI+ MS: 191.1[MH]+.

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, 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/127550; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem