Author: Jessica.F

Synthetic Route of 41716-18-1, 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 41716-18-1 as follows.

To a solution of tert-butyl (1-(4-(5-hydrazono-3-phenyl-5,6,7,8-tetrahydro-1,6- naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (22mg, 0.04 mmol) in dry DMF (1 ml_) was added EDCI (11 mg, 0.06 mmol), HOBt.H20(8 mg, 0.06 mmol) and 1-methyl-1H- imidazole-4-carboxylic acid (8 mg, 0.06 mmol) under nitrogen. The reaction mixture was heated at 60 °C overnight. After cooled down to room temperature, the mixture was partitioned between saturated NaHC03 solution and ethyl acetate. The layers were separated and the organic phase washed with water and brine, dried over Na2S04, filtered and concentrated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (method G, gradient 5 to 95percent 0.1percentFA/ACN in0.1percentFA/H2O) to give the title compound (1 mg, 5percent). NMR (500 MHz, CDCI3): 8.49 (1 H, s), 7.74 (1 H, s), 7.54 (1H, s), 7.38 (2H, d), 7.31 (2H, d), 7.28-7.23 (5H, m), 5.01 (1 H, br s), 4.94 (2H, t), 3.81 (3H, s), 3.49 (2H, t), 2.60-2.30 (4H, m), 2.10-2.01 (1 H, m), 1.85- 1.76 (1 H, m), 1.45-1.20 (9H, br).

According to the analysis of related databases, 41716-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); 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. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 7-Nitro-1H-benzo[d]imidazole

(Step 1) tert-Butyl 4-nitro-1H-benzimidazole-1-carboxylate To a suspension of 4-nitro-1H-benzimidazole (2.65 g) in tetrahydrofuran (80.0 mL), triethylamine (3.38 mL) and di-tert-butyl dicarbonate (4.25 g) were added, and the mixture was stirred at room temperature for 1 hour. 4-Dimethylaminopyridine (0.0397 g) was then added to the mixture, and the resultant mixture was stirred at room temperature overnight. After the reaction solution was concentrated under reduced pressure, the residue obtained was purified by silica gel column chromatography (chloroform/ethyl acetate). After concentration under reduced pressure, diethyl ether was added to the solid obtained to obtain a suspension, and the suspension was filtered off and dried to obtain the title compound (3.94 g) as a solid. 1H-NMR (CDCl3) delta: 1.73 (9H, s), 7.53 (1H, t, J = 8.2 Hz), 8.20-8.22 (1H, m), 8.39-8.41 (1H, m), 8.62 (1H, s). MS (m/z) :164 (M-CO2tBu+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 10597-52-1.

Reference:
Patent; Daiichi Sankyo Co., Ltd.; NAITO, Hiroyuki; KAGOSHIMA, Yoshiko; FUNAMI, Hideaki; NAKAMURA, Akifumi; ASANO, Masayoshi; HARUTA, Makoto; SUZUKI, Takashi; WATANABE, Jun; KANADA, Ryutaro; HIGUCHI, Saito; ITO, Kentaro; EGAMI, Akiko; KOBAYASHI, Katsuhiro; EP3643703; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4499-07-4,Some common heterocyclic compound, 4499-07-4, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, molecular formula is C9H13Cl2N3, 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 ligand L1 was synthesized by a condensation reaction between 2-aminoethyl-1H-benzimidazole dihydrochloride (1.170g, 5mmol), previously neutralized with K2CO3 (0.828g, 6mmol), and pyridine-2-carbaldehyde (0.535g, 5mmol) in 25mL of methanol. The reaction mixture was stirred at room temperature for approximately 2h. The resulting brown solution was removed on a rotatory evaporator and the light brown product was then filtered and recrystallized from EtOH for two times. Yield: 1.06g (85%). m.p.: 155-156C. IR (KBr pellet, cm-1): 1635(nuC=N), 1437(nuC=C-C=N). 1H NMR (500MHz, DMSO-d6, ppm) delta: 3.22-3.25 (t, 2H, -CH2-), 4.05-4.08 (t, 2H, -CH2-), 7.42-8.97 (m, 8H, Ar-H), 8.98 (s, 1H, -CH=N-), 12.61 (br s, 1H, NH). UV-Vis (methanol, lambdamax, nm): 204, 248, 276, 281. Anal. Calc. for C15H14N4: C, 71.98; H, 5.64; N, 22.38. Found: C, 71.86; H, 5.57; N, 22.29%.

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-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, its application will become more common.

Reference:
Article; Zhao, Hai-Yan; Yang, Fu-Li; Li, Na; Wang, Xiao-Jing; Journal of Molecular Structure; vol. 1148; (2017); p. 62 – 72;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 641571-11-1, COA of Formula: C11H10F3N3

General procedure: To a solution of chloroanhydride in dry CHCl3 was addedamine R2NH2 (one equivalent) and Et3N (1.5 equivalents). The reaction mixture was stirred atroom temperature. The reaction progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated from the water. The combined organic layers weredried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by columnchromatography on silica gel.

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-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 93-84-5,Some common heterocyclic compound, 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5N3O3, 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.

Concentrated hydrochloric acid (5 drops) was added to a suspension of 5-nitro-1, 3-dihydrobenzimidazol-2-one (intermediate 10,0. 96g) in phosphorus oxychloride (25ml) and the mixture was stirred and heated at reflux for 7h. The cooled mixture was poured into a mixture of ice and water and the precipitated product was extracted into ethyl acetate. The organic phase was dried (MgSO4), filtered and the filtrate was evaporated to give 2-chloro-5-nitrobenzimidazole as a tan coloured solid (0.9g). ‘H NMR (DMSO-d6) d 14.0 (brs, 1H) 8.45 (brs, 1H) 8.15 (d, 1H) 7.7 (d, 1H)

The synthetic route of 93-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARGENTA DISCOVERY LTD.; WO2005/35526; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5805-57-2, A common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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 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.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
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 25676-75-9 as follows. Computed Properties of C4H5BrN2

Step 2: preparation of benzyl 5-(1-methylimidazol-4-yl)isoindoline-2-carboxylate (compound 45b) To a solution of benzyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate (compound 45a, 76 mg, 0.20 mmol) in THF/H2O (4.5 mL, v/v = 8/1) was added 4-bromo-1-methyl-1H-imidazole (32 mg, 0.20 mmol), and K3PO4 (85 mg, 0.40 mmol). The solution was bubbled with N2 for 5 mins, then cataCXium A Pd G2 (134 mg, 0.20 mmol) was added. The mixture was heated at 75 C overnight, then cooled to rt and concentrated to give a crude product which was purified by column chromatography to give compound 45b (43 mg) as an oil. MS: calc’d 334 (MH+), measured 334 (MH+).

According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. Hoffmann-La Roche AG; The designation of the inventor has not yet been filed; (99 pag.)EP3623369; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 496-46-8, 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 496-46-8 as follows.

Synthesis of cucurbit[n]urils in methanesulphonic acid using Diethoxymethane(Ethylal)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 80 C. Ethylal (35.21 mL) was added in drop-wise and the reaction mixture was then heated to 100 C (internal temp) for 18 hours. The reaction mixture was cooled and added to acetone (410 ml) to produce a brown powder which was analysed by1H NMR.Approximate Yields b1H NMR (% of recovered product) cucurbii[5]urii 8%, cucurbit[6]uri 42%, cucurbit[7]uril 43%, cucurbit[8]uril 7%, cucurbit[9]uril 0%, cucurbit[10]uril 0%, cucurbit[ 13uril 0%.Residual formaldehyde by HPLC method was 34 ppm.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem