Category: imidazoles-derivatives

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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., Safety of Imidazole-2-carboxaldehyde

General procedure: To a mixture of formylimidazole 1 and K2CO3 in DMF, the required bromide or mesylate was added and the reaction mixture was stirred overnight under atmosphere of nitrogen at rt. The resulting suspension was cooled to room temperature (rt) and filtered. Water was added to the filtrate and the resulting solution was extracted with Et20 (3 x 25 mL). The organic layer was dried over MgS04 and evaporated to give the corresponding alkylimidazole-2- carbaldehyde. l-(3-Azidopropyl) imidazole-2-carbaldehyde oxime (RS138B). Prepared according to the general method A using formylimidazole 1 (0.50 g, 5.2 mmol), K2CO3 (0.72 g, 5.2 mmol), and 3-azidopropyl methanesulfonate (1.1 g, 6.2 mmol) in DMF (20 10 mL). Yellow oil 2f (0.62 g, 67 %).

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE SCRIPPS RESEARCH INSTITUTE; TAYLOR, Palmer; RADIC, Zoran; FOKIN, Valery; WO2015/57822; (2015); 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. 1467-16-9, name is 1H-Imidazole hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H5ClN2

Step D Preparation of 4-[(4-Chloro-phenyl)-imidazol-1-yl-methyl]-2-fluoro-benzonitrile To a solution of (4-cyano-3-fluoro-phenyl)-(4-chloro-phenyl)-methanol (2.2 g, 8.79 mmol) in acetonitrile (30 mL) was added CDI (4.28 g, 8.79 mmol) and imidazole hydrochloride (2.75 g, 8.79 mmol) and the mixture was heated at reflux for 3 hr. The acetonitrile was removed in uacuo and the residue was partitioned with EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound.

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 1467-16-9.

Reference:
Patent; Merck & Co., Inc.; US6297239; (2001); 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. 24134-26-7, name is 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole, A new synthetic method of this compound is introduced below., Safety of 2,3-Dihydro-1H-benzo[d]imidazo[1,2-a]imidazole

General procedure: A solution of 2 mmol of compound 1-3 and 2.1 mmol of BrCH2C6H4C6H4R-o or ethyl 4-(bromomethyl)benzoate in 10 ml of CH3NO2 was boiled for 7.5 h. The reaction mixture was cooled and left for two days at 5 C. The precipitated hydrobromide was filtered and washed with acetone.

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; Babkov, Denis A.; Zhukowskaya, Olga N.; Borisov, Alexander V.; Babkova, Valentina A.; Sokolova, Elena V.; Brigadirova, Anastasia A.; Litvinov, Roman A.; Kolodina, Alexandra A.; Morkovnik, Anatolii S.; Sochnev, Vadim S.; Borodkin, Gennady S.; Spasov, Alexander A.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 17; (2019); p. 2443 – 2447;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

A solution of compound (4a-b) (4 g, 0.022 mol) in absoluteethanol (15 mL) was refluxed for 7 h in presence of conc. H2SO4(0.1 mL). After completion of the reaction, it was cooled to roomtemperature, then 2.14 ml (0.044 mol) of hydrazine hydrate wasadded and the reaction was further refluxed for another 8 h.Detecting single-spot in TLC using the solvent system chloroform:methanol (9:1), the reaction mixture was poured in ice. A precipitateformed (6a-b) which was filtered, washed with water andcrystallized from ethanol. 4.4.1. 2-(1H-benzo[d]imidazol-2-yl)acetohydrazide (6a, C9H10N4O)white flakyYield 86%, mp 120-122 C; Rf 0.40 [chloroform: methanol(9:1)]; IR (KBr) (cm1): 3360 (NH str), 1733 (C]O); 1H NMR(300 MHz, DMSO-d6) delta(ppm): 3.66 (s, 2H, NH2), 4.28 (s, 2H, CH2C] O), 7.11e7.12 (d, 2H, J 3.6, H-5,6 benzimidazole), 7.47 (s, 2H, H-4,7benzimidazole), 9.36 (s, 1H, eNHNH2), 12.22 (bs, 1H, NH benzimidazole,D2O exchangeable). 13C NMR (75 MHz, DMSO-d6) delta(ppm): 164.38, 149.56, 137.68, 133.50, 125.50, 121.27, 45.06. Anal.Calcd.: C, 56.83; H, 5.30; N, 29.46; Found: C, 56.85; H, 5.34; N, 29.43.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Akhtar, Md Jawaid; Siddiqui, Anees Ahmad; Khan, Ahsan Ahmed; Ali, Zulphikar; Dewangan, Rikeshwer Prasad; Pasha, Santosh; Yar, M. Shahar; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 853 – 869;,
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 104619-51-4 as follows. COA of Formula: C7H7N5

Example 2: r4-(5-Amino-M ,3,41oxadiazol-2-yl)-pyridin-3-v?-(2-fluoro-4-iodo- phenvD-amine; To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isoniotacotiniotac acid hydrazide (1g, 2.68mmol) in DMSO (6mL) were added 1 ,1 -di-1 H-imidazol-1-yl-methyleneamine (864mg, 5.36mmol). The reaction mixture was stirred at RT for 18h. Quenching of the reaction by adding water (6OmL). A solid precipitated out. The solid was filtered, washed with water and cold methanol. Yield: white solid 1.Og. LC-MS (Method A) [4.66min; 398(M+1)].

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); 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. 930-62-1, name is 2,4-Dimethylimidazole, A new synthetic method of this compound is introduced below., SDS of cas: 930-62-1

Preparation 14 Ethyl N-trifluoroacetyl-N-(2-nitro-5-[2,4-dimethylimidazol-1-yl]benzyl)glycinate STR36 A mixture of 2,4-dimethylimidazole (6.25 g), ethyl N-trifluoroacetyl-N-(5-fluoro-2-nitrobenzyl)glycinate (22.0 g) and sodium carbonate (6.62 g) was stirred and heated at 130 for 2 hours. Volatile material was removed from the cooled mixture in vacuo and the residue was partitioned between ethyl acetate (200 cm3) and water (100 cm3). The organic phase was washed with water (2*25 cm3), dried (MgSO4), and evaporated in vacuo to give an oil which was chromatographed on silica (Merck “MK 60.9385” [Trade Mark]) eluding with ethyl acetate:methanol, 1:19. Combination and evaporation of the appropriate fractions gave an oil which crystallized on trituration with ether to afford the title compound, m.p. 172.5-176 (3.1 g). Analysis %: Found: C,50.7; H,4.8; N,12.7; Calculated for C18 H19 F3 N4 O5: C,50.5; H,4.5; N,13.1.

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4783467; (1988); A;,
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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), This compound has unique chemical properties. The synthetic route is as follows., name: 1H-imidazol-2-amine sulfate(2:1)

2-Aminoimidazole sulfate (1.53 g) is dissolved in 0.97 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. A solution of 799 mg of NaNO2 in 2 mL of water is added dropwise, and the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.65 g of 1,4-diallyl-1,2,3,4-tetrahydroquinoxaline, 1.9 g of sodium acetate and 10 mL of acetic acid is cooled to 0 C. The diazonium solution is added slowly to this slurry while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and the dark solid is dried. (E)-6-((1H-imidazol-2-yl)diazenyl)-1,4-diallyl-1,2,3,4-tetrahydroquinoxaline (2.3 g) is used in the next step without further purification.

According to the analysis of related databases, 1450-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3034-41-1, A common heterocyclic compound, 3034-41-1, name is 1-Methyl-4-nitroimidazole, molecular formula is C4H5N3O2, 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.

Intermediate 10; 2-Chloro-N-(l-methyl-lH-imidazol-4-v?-7-r(4-methylphenyl)sulfonyl1-7H-pyrrolor2.3- J1pyrimidin-4-aminel-Methyl-4-nitro-lH-imidazole (Intermediate 1, 50 mg, 0.39 mmol) was dissolved in ethanol (5 mL) and Pd/C (5 wt%, Degussa, 20.93 mg, 9.83 mumol) was added. The reaction mixture stirred under 1 atm of hydrogen at r.t. for 3 hours and was then filtered through diatomaceous earth (Celite brand) to give 1 -methyl- lH-imidazol-4-amine. 2,4-Dichloro-7-[(4- methylphenyl)sulfonyl]-7H-pyrrolo[2,3-Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Synthesis of 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride To a suspension of 4-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (100 mg, 0.32 mmol), 1-methyl-1H-imidazole-4-carboxaldehyde (70 mg, 0.64 mmol) and acetic acid (37 muL, 0.64 mmol) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (203 mg, 0.96 mmol) at ambient temperature. After stirring for 16 hours, the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (*3). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica column chromatography, eluting with 2-10% methanol in dichloromethane to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (84 mg, 71% yield). To 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide (125 mg, 0.34 mmol) in ethyl acetate (10 mL) and dichloromethane (2 mL), was added 2M HCl in diethyl ether (0.17 mL, 0.34 mmol). The solvent was removed under reduced pressure. The resulting solid was triturated with diethyl ether and the liquors decanted. The solid was dried, dissolved in water and freeze-dried to yield 4-((1R,5S,9r)-9-methoxy-3-((1-methyl-1H-imidazol-4-yl)methyl)-3-azabicyclo[3.3.1]nonan-9-yl)picolinamide hydrochloride (83 mg, 60% yield). [M+H]+ 370.15. 1H NMR (400 MHz, D2O): 8.60 (d, 1H), 8.21 (s, 1H), 7.98 (s, 1H), 7.60 (d, 1H), 7.54 (s, 1H), 4.33 (s, 2H), 3.74 (s, 3H), 3.61 (d, 2H), 3.48 (d, 2H), 2.92 (s, 2H), 2.67 (s, 3H), 1.85-1.68 (m, 2H), 1.56-1.42 (m, 4H).

According to the analysis of related databases, 17289-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alkermes, Inc.; Wynn, Thomas Andrew; Alvarez, Juan C.; Moustakas, Demetri Theodore; Haeberlein, Markus; Pennington, Lewis D.; US2019/241524; (2019); 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. 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClF3N2

Example 1 8-(5-(Trifluoromethyl)-1H-benzo[d]imidazol-2-yloxy)quinolin-2-ol A mixture of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1), 2,8-dihydroquinoline (48 mg, 0.3 mmol, Fluka) and N,N-diisopropylethylamine (0.1 mL, 0.58 mmol, Aldrich) in EtOH (2 mL) was subjected to microwave irradiation at 180 C. with stirring for 60 min. The reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluding with 80% EtOAc/hexane to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 346 (M+1).

According to the analysis of related databases, 86604-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Norman, Mark H.; Ognyanov, Vassil I.; Wang, Xianghong; US2006/160872; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem