Category: imidazoles-derivatives

These common heterocyclic compound, 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, 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. COA of Formula: C4H6N4O

A solution of 5-amino-1H-imidazole-4-carboxamide (35 g, 277 mmol) in MeSO3H (150 mL) and EtOH (560 mL) was stirred at reflux conditions for 2 days, and then concentrated in vacuo. To the resulting residue, water (400 mL) was added and while stirring and cooling (ice/water) sodium hydroxide solution (32 %) was added until pH = 7 was reached. The water layer was saturated with sodium chloride and extracted with DCM (200 mL x 3). The combined organic layers were dried (MgSO4), and filtered. The filtrate was concentrated in vacuo to afford ethyl 5-amino-1H-imidazole-4-carboxylate (13.7 g, 45%) as a white solid.

The synthetic route of 4-Amino-1H-imidazole-5-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GREENLEE, William, J.; GOOD, Andrew, C.; (309 pag.)WO2017/176961; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 496-46-8, A common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, 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.

CB[7] was synthesized according to the published procedures[35, 36]. Reaction of glycoluril with formaldehyde in 9 M sulfuric acid at ~ 75 C for 24 h and then at ~ 100 C for12 h yielded a mixture of CB[n]. After the reaction, the mixture was poured into water, acetone was added to produce precipitate. The precipitate was separated by decantation,washed with water/acetone, and filtered. From the acetone/water soluble portion, CB[7] were isolated by fractional crystallization/precipitation and further purified by recrystallizatio.The prepared CB[7] has a purity of 99% and ayield of 24%. Anal. Calc. for C42H42N28O14(M = 1162.96 g/mol): C: 43.34%, H: 3.61%, N: 33.71%, O: 19.26%. Found:C: 42.62%, H: 3.47%, N: 34.47%, O: 18.69%. 1H-NMR(400 MHz, D2O,TMS, ppm): delta5.76(1H, d, H-1 of CB),4.21(1H, d, H-2 of CB), 5.49(1H, s, H-3 of CB).

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Chuanzhu; Jia, Chunyan; Li, Yamin; Liao, Xiali; Yang, Bo; Zhang, Xinzhong; Zhong, Yunshuang; Journal of Inclusion Phenomena and Macrocyclic Chemistry; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 144690-33-5, 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. 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 5: The reaction part was charged with ethyl 4- (1-hydroxy-1-methylethyl) -2-propyl-1- {4- [2- (trityltetrazol-5-yl) phenyl] 22 g of 5-carboxylate (Formula 4), 3.1 g of sodium hydroxide and 90 mL of ethanol were added and the mixture was stirred at 20 to 25 C for 4 to 5 hours. When the reaction was completed, the reaction solution was concentrated. To the residue were added 50 mL of ethyl acetate and 50 mL of purified water. The mixture was stirred for 1 hour and then layered. The separated organic layer was washed twice with an aqueous solution containing 30 g of salt and 170 mL of purified water. 1 g of activated carbon and 20 g of anhydrous sodium sulfate were added to the organic layer, followed by stirring for 30 minutes to 1 hour, followed by filtration Respectively. After the filtrate was concentrated under reduced pressure, 50 mL of N, N-dimethylacetamide was added to the residue, the temperature was adjusted to 5 to 10 DEG C 4 g of potassium carbonate was added and 6.2 g of 4- (chloromethyl) -5-methyl-1,3-dioxol-2-one (Formula 6) was dissolved in N, N-dimethylacetamide 6 ML was added dropwise, and the mixture was reacted at 45 to 50 C for 4 hours with stirring. When the reaction is completed, the reaction solution is cooled to 20 to 25 After cooling, 220 mL of ethyl acetate, 30 g of salt and 170 mL of purified water were added successively. The organic layer was separated And then washed once more with an aqueous solution containing 30 g of salt and 170 mL of purified water. The organic layer was washed with 1 g of activated carbon, 20 g of sodium was added and stirred for 30 minutes to 1 hour, followed by filtration. The filtrate was concentrated under reduced pressure, and then acetone 100 mL of i-tril was added, and the mixture was stirred at 50 to 55 C for 1 hour. The crystals were cooled to 0 to 5 [deg.] C and stirred for 2 hours. Followed by washing with 50 mL of isopropyl alcohol, followed by drying to obtain 21.6 g (yield: 88%) of tritylolemecanemethoxysilane (formula 1a) Purity 99.97%) was obtained

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DONGBANG FTL CO., LTD; Song, Tae Hong; Jung, Hun Suk; Jang, Do Yeon; Moon, Chung Sun; Jung, Hee Jung; (18 pag.)KR101526249; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5465-29-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5465-29-2 name is 2-Propylbenzimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

in 200 ml of water800 ml of concentrated sulfuric acid (i.e., 80% concentration), and 50.0 g of 2-propylbenzimidazole was added dropwise30% hydrogen peroxide 500ml, the reaction exothermic reflux, control the rate of dropping to keep the reaction solution has been boiling. After completion, the reaction was continued for 3 hours. Add water 1000ml, cold to room temperature. The solid was precipitated, and the mixture was stirred at 0 to 5 C for 3 hours, filtered, washed with water, and washed with 5% aqueous sodium sulfite solution (100 ml). The resulting solid column chromatography (eluent: water: methanol = 2: 1, ) Was imidazole-4,5-dicarboxylic acid 3 · lg, mp 267.3 C melting at the same time decomposition.

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

Reference:
Patent; Huanggang LUBAN Pharmaceutical Co.,Ltd. (LUBAN); YANG, XIAOLONG; LIU, XIANGQUN; LI, QIANG; CHEN, QIAN; YANG, TIEBO; (17 pag.)CN104262260; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10111-08-7, 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. 10111-08-7, name is Imidazole-2-carboxaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Part A Preparation 2-hydroxymethyl-1H-imidazole 2-Imidazolecarboxyaldehyde (5.0 g, 52.0 mmol) was suspended in 200 mL of methanol. NaBH4 (3.95 g, 0.10 mol) was added portion-wise. The reaction mixture was stirred at room temperature for 1 h under N2. It was quenched with 10 mL of brine. The solvent was removed. The solid was washed with 5% MeOH in CH2Cl2. The inorganic solid was filtered off. The filtrate was concentrated and chromatographed with 5% MeOH in CH2Cl2 to give 2.32 g off-white solid (45.2% yield). 1H NMR (DMSO-d6): delta 6.86 (s, 2H), 4.40 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis Imidazole-2-carboxaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Quan, Mimi L.; US2003/144287; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-38-6, A common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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.

To a solution of 4-nitroimidazole (5.00 g, 44.2 mmol) in MeOH (40 ml) was added phenylboronic acid (8.77 g, 71.7 mmol), CuC (0.710 g, 5.30 mmol) and NaOH (1.760 g, 44.2 mmol) at rt. The reaction mixture was stirred at 80C for 16 h whilst slowly purging with O2 gas throughout the reaction time. The resulting mixture was cooled to rt and concentrated under reduced pressure. The obtained crude material was poured into water (500 ml) and extracted with EtOAc (3 x 150 ml). The combined organic phase was wash with NaHCO3 solution (200 ml) and dried over Na2SO4, filtered and concentrated under reduced pressure to yield 4-nitro-1 -phenyl- 1 H-imidazole (1 .500 g, 7.93 mmol). LCMS: Method C, 1 .760 min, MS: ES+ 191 .09.

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (167 pag.)WO2018/65768; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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 1546-79-8, SDS of cas: 1546-79-8

The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol) was dried by coevaporation with dry MeCN (3 mL) under Ar and dissolved in a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight. The resultant solution was added to the compound 6a (40.1 mg, 50 mumol), which was dried by coevaporation with dry MeCN prior to use, and the resultant mixture was stirred for 20 min at rt under Ar. N-(Trifluoroacetyl)imidazole (17.0 muL, 0.15 mmol) and i-Pr2NEt (44.0 muL, 0.25 mmol) were added and the mixture was stirred for 30 min at rt. Then DTD (31.9 mg, 0.15 mmol) was added and the mixture was stirred for 50 min at rt. The mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane (5.0 mL). A 6 vol% DCA solution in dichloromethane (5.0 mL) and Et3SiH (1.2 mL, 7.5 mmol) were added and the mixture was stirred for 20 min at rt. The mixture was washed with saturated NaHCO3 aqueous solutions (3 × 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 × 10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by FSPE [1.6 cm column id, 4.8 g of fluorous silica gel, methanol-H2O 16 mL (80:20, v/v) then THF 25 mL] to give 13t (73.3 mg, colorless foam), which was analyzed by 31P NMR (121 MHz, CDCl3) delta 68.9.

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, 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Oka, Natsuhisa; Murakami, Ryosuke; Kondo, Tomoaki; Wada, Takeshi; Journal of Fluorine Chemistry; vol. 150; (2013); p. 85 – 91;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, 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. Safety of (1H-Imidazol-1-yl)(phenyl)methanone

General procedure: In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol (1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a spatula. CO2 gas starts releasing with increase in temperature and solid reaction mixture was turned to pale yellow liquid within 5 min. 0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine, and 1 mL of water were added to it. The reaction mixture was kept at room temperature for another 10 min. Dilute hydrochloride solution was added to it and the aqueous layer was washed with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to give pure product.

The synthetic route of 10364-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Verma, Sanjeev K.; Ghorpade, Ramarao; Pratap, Ajay; Kaushik; Tetrahedron Letters; vol. 53; 19; (2012); p. 2373 – 2376;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 934-22-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 934-22-5 name is 6-Aminobenzimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
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., COA of Formula: C8H4ClF3N2

17. 5-Trifluoromethyl-2-[(4-methoxy-2-pyridylmethyl)thio]-(1H)-benzimidazole 22.1 g (0.1 mole) of 5-trifluoromethyl-2-chlorobenzimidazole and 15.7 g (0.11 mole) of 4-methoxy-2-thiomethylpyridine in 250 ml of isopropanol are heated under reflux for 10 hours. The solvent is stripped off in vacuo, and 500 ml of ice water are added to the residue. The title compound is filtered off with suction and recrystallized from acetonitrile. M.p. 180-182 C.

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; Byk Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4472409; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem