Category: imidazoles-derivatives

Electric Literature of 872-82-2,Some common heterocyclic compound, 872-82-2, name is 2-(1H-Imidazol-5-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.

General procedure: A mixture of imidazole derivatives (4a-c, 10mmol), 4-amino-6-chloropyrimidine (1.30g, 10mmol), and K2CO3 (2.07g, 15mmol, for 5a) or Cs2CO3 (3.91g, 12mmol, for 5b-c) was stirred in DMF (20mL) at 100C (for 5a) or at 140C (for 5b-c) for 12h. Water (100mL) was then added. The mixture was extracted with EtOAc (3×50mL). The organic layer was separated and dried over Na2SO4. Removal of the solvents produced a residue which was purified using column chromatography and eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v) to afford 5a-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-(1H-Imidazol-5-yl)ethanol, its application will become more common.

Reference:
Article; Xu, Yi-xiang; Wang, Huan; Li, Xiao-kang; Dong, Sheng-nan; Liu, Wen-wen; Gong, Qi; Wang, Tian-duan-yi; Tang, Yun; Zhu, Jin; Li, Jian; Zhang, Hai-yan; Mao, Fei; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 33 – 47;,
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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O

lb lb. 3-({4-[(2-Hydroxyethyl)(methyl)carbamoyl]phenyl}({l-[(4-methyl-lH-imidazol-5-yl)methyl]piperidin-4-ylidene})methyl)benzamide 3-({4-[(2-Hydroxyethyl)(methyl)carbam benzamide (79.0 mg, 0.2 mmol) was dissolved in 1 ,2-dichloroethane (2 mL) and acetic acid (57 muIota_, 1 .0 mmol) was added followed by 5-methylimidazole-4-carboxaldehyde (44.0 mg, 0.4 mmol) and NaBH(OAc)3 (169 mg, 0.8 mmol). The reaction was stirred at 50C for 48 h. The crude was purified by flash chromatography (ethyl acetate, ethyl acetate/methanol 75:25) to give the title compound as a crude material. This material was then purified by preparative HPLC (X-bridge column, 50 mM NH4HCO3 as mobile phase, CH3CN from 10 to 40) to give 5 mg of the title compound. MS m/z 488 [M+H]+.

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMNOVO AB; VON MENTZER, Bengt; STARKE, Ingemar; BRANDT, Peter; (24 pag.)WO2016/99394; (2016); 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 68282-53-1

A solution of 3-methoxy-/V-((4-methyl-1 H-imidazol-5-yl)methylene)aniline in ethanol was prepared by heating a solution of 4-methyl-1 /-/-imidazole-5-carbaldehyde (0.1 10 g; 0.999 mmol) and 3-methoxyaniline (0.1 15 mL; 1.023 mmol) in ethanol (0.7 mL) at 65C for 24 h. The formation of the imine was quantitative and the solution was used without further purification. ESI/APCI (+): 216 (M+H). ESI/APCI (-): 214 (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 68282-53-1.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound has unique chemical properties. The synthetic route is as follows.

Example 2: Synthesis of cucurbituril homologues; [27] 3 g of paraformaldehyde was added to 5.68g of glycolurils of formula 9 and 20 mL of a 9M sulfuric acid was added thereto. Then, a 800W microwave was irradiated to the reaction mixture for 45 seconds. [28] The reaction solution was recrystallized with acetone and methanol to thereby synthesize and separate four cucurbituril homologues, CB[5], CB[6], CB[7], and CB[8 ], as represented by formula 1 where X is 0, Rand R are H, and n is 5,6, 7, and 8, respectively. The yields of CB[5], CB[6], CB[7], and CB[8] were 15%, 45%, 20%, and 15%, respectively. [29] CB [5]:¹ H (500 MHz, D 2O/CF CO DID SO 4 (1:1:0.15)): No. 4.43 (d, J = 15.5 Hz, 10H), 5.65 (s, 10H), 5.85 (d, J =15.5 Hz, lOH). [30] CB [6]:¹ H (500 MHz, D 2 O/CF 3CO2 DID 2 SO 4 (1: 1:0.15)): No. 4.35 (d, J = 15.5 Hz, 12H), 5.61 (s, 12H), 5.69 (d, J =15.5 Hz, 12H). [31] CB [7]:¹ H (500 MHz, D 2 O/CF 3CO2 DID 2 SO 4 (1: 1:0.15)): No. 4.29 (d, J = 15.5 Hz, 14H), 5.60 (s, 14H), 5.91 (d, J =15.5 Hz, 14H). [32] CB [8]:¹ H (500 MHz, D 2 O/CF 3CO2 DID 2 SO 4 (1: 1:0.15)): No. 4.28 (d, J = 15.5 Hz, 16H), 5.60 (s, 16H), 5.93 (d, J =15.5 Hz, 16H).

The chemical industry reduces the impact on the environment during synthesis Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; POSTECH ACADEMY-INDUSTRY FOUNDATION; WO2005/103053; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, 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 152628-03-0, name: 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid

1.2 kg of isoamyl alcohol was added to the reaction flask.Add 2-n-propyl-4-methyl-6-carboxybenzimidazole (400 g, 1.83 mol) and stir.Methanesulfonic acid (176 g, 1.83 mol, 1.0 eq) was added and N-methyl-phenylenediamine hydrochloride (360 g, 1.85 mol) was added.The temperature was raised to 130-135 C to reflux and the reaction was carried out for at least 18 hours until no significant moisture was separated. After the reaction is completed, cool to about 70 C,Add 2000 ml of water, stir, adjust the pH to 6~7 with 30% NaOH solution, stir and cool to 20~25 C after completion, and filter to obtain the product, the yield is 93.0%, and the HPLC purity is 99.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Weihai Disu Pharmaceutical Co., Ltd.; Disha Pharmaceutical Group Co., Ltd.; Li Xinfa; Cui Dapeng; (6 pag.)CN104974096; (2019); B;,
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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example No. 302Preparation of 5- (3 , 4 -dihydro-2H-benzo [b] [1,4] oxazin-6-yl) -N- (2-methyl-lH-benzo [d] imidazol-5-yl) -lH-pyrazolo [4,3- d] pyrimidin-7-amine6- (7-chloro-2- (4 -methoxybenzyl) -2H-pyrazolo [4 , 3-d] pyrimidin-5- yl) -2H-benzo [b] [1 , 4] oxazin-3 (4H) -one (0.16 mmol) and 2 -methyl – lH-benzo [d] imidazol-5-amine (0.3 mmol 2 eq.,) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The reaction mixture was dissolved in THF (dry) LiAlH4 powder was added (excess, 2 by 2 eq) until completion of reaction is observed (by LCMS) . The reaction was quenched with water (lmL per gram LiAlH4) , then NaOH (ca. 15% aq. , lmL per g LiAlH4) , water (3mL per gram LiAlH4) . The mixture was filtered, washed with THF, MeOH, MeCN (ca. 10ML each) . The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was concentrated and purified by semi-preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 398.1840 g/molHPLC-MS: analytical method Lrt: 3.09 min – found mass: 399 (m/z+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 29043-48-9.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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.

[00535] lH-Imidazole-2-carboxylic acid { 3-r4-(6-cyclohexylamino-9H-purin-2-ylamino)-3-methylphenoxylpropyl|amide (C14): Diisopropylethyl amine (0.10 g, 0.81 mmol) was added to a solution of lH-imidazole-2-carboxylic acid (0.025 g, 0.22 mmol), N- 2-[4-(3-aminopropoxy)-2-methyl-phenyl]-N-6-cyclohexyl-9H-purine-2,6-diamine (0.08 g, 0.20 mmol), EDCI (0.046 g, 0.24 mmol), and HOBt (0.037 g, 0.24 mmol) in DMF (1.0 mL), and the resulting mixture was stirred overnight at ambient temperature. The solvent was removed and the crude material was purified by reverse-phase HPLC to provide compound (Table 1, C14).

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MYRIAD PHARMACEUTICALS, INC.; KUMAR, Dange, Vijay; MCALEXANDER, Ian, A.; BURSAVICH, Matthew, Gregory; HOARAU, Christophe; SLATTUM, Paul, M.; GERRISH, David, A.; LOCKMAN, Jeffrey, W.; JUDD, Weston, R.; SAUNDERS, Michael; PARKER, Daniel, P.; ZIGAR, Daniel, Feodore; KIM, In, Chul; WILLARDSEN, J., Adam; YAGER, Kraig, M.; SHENDEROVICH, Mark, D.; WILLIAMS, Brandi, L.; TARDIF, Keith, D.; WO2010/111406; (2010); A2;,
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. 1072-62-4, name is 2-Ethyl-1H-imidazole, A new synthetic method of this compound is introduced below., Formula: C5H8N2

(a) 3-[3-(2-Ethylimidazol-l-ylmethyl)phenyl]-5-z^o-butyl-7V-fe7Y-butylthiophene- 2-sulfonamide; To a solution of 3-(3-bromomethylphenyl)-5-ziO-butyl-7V-fe7t-butylthiophene-2- sulfonamide (70 mg, 0.158 mmol; see Example l(e)) in dioxane (2.0 mL) was added 2-ethylimidazole (45.4 mg, 0.473 mmol) and the reaction mixture was stirred for 1 h at 80C. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography using MeOH:CH2Cl2 (6:94) as EPO eluent to give the sub-title compound in 85% yield as a colourless syrup (61.2 mg, 0.134 mmol).1H NMR delta (CDCl3): 0.95(s, 9H)5 0.96 (d, J= 6.5 Hz5 6H), 1.29 (t, J= 7.3 Hz5 3H)5 1.80-1.98(m, IH), 2.58-2.72 (m, 4H)5 4.11 (br s, IH)5 5.08 (s, 2H)5 6.70 (s, IH), 6.88 (s5 IH)5 6.98 (s, IH)5 7.08 (d, J – 7.7 Hz5 IH)5 7.39 (apparent t, J = 7.7Hz, IH)5 7.42 (s5 IH)5 7.51 (d, J= 7.7 Hz5 IH).13C NMR delta (CDCl3): 11.9, 20.2, 22.1, 29.4, 30.5, 39.1, 49.1, 54.5, 119.6, 126.7, 127.5, 127.7, 128.5, 128.7, 129.0, 135.5, 136.6, 136.9, 142.3, 148.5, 149.4. IR v (neat, cm”1): 3283, 3053, 2966, 2870, 1493, 1465, 1430, 1313. MS (ESI) m/z: 460 (M+H)+.Anal. Calcd. for C24H33N3O2S2- 1/2H2O: C, 61.50; H, 7.31; N, 8.97. Found: C, 61.53; H, 7.36; N5 8.99.

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; VICORE PHARMA AB; WO2006/109048; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 930-62-1, 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 930-62-1 as follows.

Intermediate 27: 2,4-Dimethyl-1-trityl-1H-imidazole; A solution of trityl chloride (15 g, 55 mmol) in dichloromethane (50 mL) was added drop wise over 45 minutes to a solution of 2,4-dimethyl imidazole (5 g, 52 mmol) in a mixture of dichloromethane (100 mL) and triethylamine (11.3 mL, 81 mmol) at room temperature. The mixture was stirred over night, then quenched with methanol (4 mL) and stirred for additional 30 minutes. The solvent was evaporated, the residue taken up in toluene (600 mL), washed with potassium phosphate buffer (pH 7, 1M, 2x 200 mL) and with water (200 mL). The organic phase was diluted with dichloromethane (200 mL), dried over sodium sulfate, and concentrated under reduced pressure to -100 mL. Hexanes (100 mL) were added and the precipitated was collected by filtration and washed with hexanes (2x 50 mL) to give 14.76 g (84 %) of the product as a colourless solid. ¹H-NMR (CDCl3) 5: 1.62 (s, 3H); 2.16 (s, 3H); 6.40 (s, 2H); 7.10-7.40 (m, 15H).

According to the analysis of related databases, 930-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/116022; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 84946-20-3, 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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, 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 mixture of 1d (1.0 eq.) and ethanolamine (10 eq.) was heated to 150 C for 30 min by use of microwave irradiation. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated solid was filtered and washed with diethyl ether. The crude product was purified by flash column chromatography (MeOH/methylene chloride) to give desired product 1e.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Article; Oh, Sangmi; Kim, Sungbum; Kong, Sunju; Yang, Gyongseon; Lee, Nakyung; Han, Dawoon; Goo, Junghyun; Siqueira-Neto, Jair L.; Freitas-Junior, Lucio H.; Song, Rita; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 395 – 403;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem