Author: Jessica.F

Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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. Formula: C6H6N4O2S

(I) 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose (3)(1.0 g; 4.0 mmol) was dissolved in DMF (20 ml), cooledat 0 C and under N2-atmosphere NaH (0.14 g; 6.0 mmol)was added to the solution. The suspension was stirred for30 min and cooled to -35 to -40 C. After N?,N-sulfonyldiimidazole(1.2 g; 6.0 mmol) in DMF (12 ml) was droppedto the reaction mixture and stirred for 30 min again at-40 C. MeOH was added (0.8 ml) to the solution andstirred for 30 min at -40 C. The solution was poured intoice-water (200 ml). The precipitate was filtered, washedwith cold water to get the white crystalline product 11(1.2 g; 80%). M.p.: 97-98 C; lit. m.p. (Vatle and Hanessian1996): 98-99 C; Rf = 0.70 (EtOAc-hexane 1:1).(II) From 3 (25.0 g; 96.0 mmol) the yield was 84% (31.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7189-69-7, its application will become more common.

Reference:
Article; Nagy, Adrienn; Csordas, Barbara; Zsoldos-Mady, Virag; Pinter, Istvan; Farkas, Viktor; Perczel, Andras; Amino Acids; vol. 49; 2; (2017); p. 223 – 240;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 57090-88-7,Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (3.2 g, 11.98 mmol), 1 H-imidazole-4-carbonitrile (2.017g, 14.37 mmol) and ethyl-diisopropyl-amine (8.4 ml, 47.9 mmol) in 10 ml of dioxane is heated to reflux for 24 hours. The solution is allowed to cool to room temperature and evaporated. The residue is chromatographed on silica gel using gradients of dichloromethane and methanol to give 0.36 g (1.05 mmol, 8.8percent) of amorphous 5-(4-cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoicacid methyl ester, ES-MS: m/z 341 [M+Hf.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4-carbonitrile, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/10591; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 40197-20-4, 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. 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-1H-benzo[d]imidazole-2-carboxylic acid (1 eq) was dissolved in DMF, to which morpholine (1.01 eq),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.1 eq), 1-hydroxybenzotriazole (HOBT, 1.1 eq), and TEA (3 eq)were added stepwise, followed by stirring at room temperature for overnight. The reaction was terminated with a smallamount of water, followed by extraction using water and EtOAc. The small amount of water remaining in the organiclayer was dried over anhydrous MgSO4. The solvent was eliminated by vacuum distillation, followed by vacuum drying.Then, a target compound was obtained by column separation with the yield of 29%. 1H NMR (300MHz, CDCl3) delta 7.77-7.65 (m. 1H), 7.43-7.41 (m, 2H), 3.85-3.82 (m, 8H).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); KIM, Eunhee; YOO, Sung-Eun; KANG, Nam Sook; KOO, Tae-Sung; PARK, Min-Young; KIM, Young-Hoon; BAE, Hyun-Ju; KIM, Jin-Woo; IN, Tae-Kyu; JOO, Choun-Ki; (101 pag.)EP3176163; (2017); 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., Application In Synthesis of 1-Methyl-1H-imidazole-4-carbaldehyde

N-Boc-piperazine (0.470 g, 2.50 mmol, 1.1 eq) was dissolved in DCM (6.2 mL). To this solution, 1-methyl-1H-imidazole-4-carboxaldehyde (0.250 g, 2.27 mmol, 1 eq) was added followed by chlorotitanium triisopropoxide (1.19 mL, 5.0 mmol, 2.2 eq). The resulting solution was stirred at room temperature for 10 min before the addition of sodium triacetoxyborohydride (2.40 g, 11.3 mmol, 5 eq). The mixture was stirred at room temperature for 17 h and was diluted with EtOAc (12 mL). It was then poured into ammonia (35% sol. in H2O, 6 mL) and the resulting mixture filtered and washed with EtOAc. The organic phase was washed with H2O dried (MgSO4) and the solvent removed in vacuo. The crude material was purified by column chromatography on a Biotage SP1 system eluting with methanol (1-8%) in dichloromethane to give the title compound as a clear oil (0.390 g, 62%); 1H-NMR (500 MHz, CDCl3): delta 1.46 (s, 9H, C(CH3)3), 2.48 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.45 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 3.52 (s, 2H, NCH2), 3.66 (s, 3H, imidazole Me), 6.80 (s, 1H, imidazole 5-H), 7.38 (s, 1H, imidazole 2-H); LC (Method B)-MS (ESI, m/z): 281 [(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 17289-26-8.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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. Product Details of 28890-99-5

500ml of four bottles,In the atmosphere of nitrogen gas,0.01 mol of 5H-benzimidazol [1,2-a] benzimidazole was added,0.05 mol (6-bromo-9-phenyl-9H-carbazol-3-yl) -di-dibenzofuran-4-yl-0.03 mol of sodium tert-butoxide,1 x 10-4 mol Pd2 (dba) 3,1 x 10-4 mol tri-tert-butylphosphine,250ml toluene,Heated to reflux for 24 hours,Sampling point plate, antiShould be completely, natural cooling, filtration, the filtrate steamed, silica gel column, get the target product,Purity 99.10, yield 36.00%.

The synthetic route of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Sanyue Photoelectric Technology Co., Ltd.; Li, Chong; Xu, Kai; Zhang, Zhaochao; Ye, Zhonghua; Wang, Lichun; (29 pag.)CN106467549; (2017); A;,
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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Formula: C8H7BrN2

A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1 ,4-dioxane (1 mE) was sonicated and added undernitrogen to a mixture of 6-bromo-1-methyl-benzimidazole (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mE). The mix-ture was stirred at 1100 C. for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator and concentrated. The residue was purified by prep HPEC to yield the desired product (Compound A).MW: 262.3. MS Ms?d: 263.2.NMR: 1H NMR (400 MHz, DMSO-d6): oe=8.13 (1H, s), 7.68 (1H, dd), 7.60 (1H, dd), 7.54 (1H, d), 7.32 (1H, d), 7.24 (1H, t), 6.91 (1H, dd), 3.77 (3H, s), 3.39 (3H, s).

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; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (1H-Benzo[d]imidazol-2-yl)methanamine

General procedure: To the triazole carbamate ester of MMB (7) (0.167 mmol) indichloromethane (2 mL) was added the appropriate imidazole orbenzimidazole amine (0.167 mmol) at ambient temperature, andthe reaction mixture was stirred for 4-16 h. After completion ofthe reaction (monitored by TLC), water was added and the resultingmixture extracted with dichloromethane. The organic liquorswere separated, washed with water, followed by brine solution,dried over anhydrous Na2SO4, filtered, and the solvent removedto afford the crude reaction product. The crude product was purifiedby column chromatography (silica gel, 2-5% methanol indichloromethane) to afford the appropriate carbamate derivativeof MMB as a white solid (yield: 65-75%).

According to the analysis of related databases, 5805-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Albayati, Zaineb A.F.; Janganati, Venumadhav; Chen, Zheng; Ponder, Jessica; Breen, Philip J.; Jordan, Craig T.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry; vol. 25; 3; (2017); p. 1235 – 1241;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 305790-48-1,Some common heterocyclic compound, 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C8H7BrN2O, 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 5-bromo-3-methyl-1H-benzimidazol-2-one (4.90 g, 21.6 mmol, Intermediate IP) in THF (300 mL) was added t-BuOK (3.63 g, 32.3 mmol) at 0 C. The mixture was stirred at 0-10 C. for 1 hour under N2. Then a solution of [1-[(4-methoxyphenyl) methyl]-2,6-dioxo-3-piperidyl] trifluoromethanesulfonate (9.87 g, 25.9 mmol) in THF (100 mL) was added to the reaction mixture at 0-10 C. during 30 minutes. The mixture was stirred at 0-10 C. for 30 minutes under N2. An additional solution of [1-[(4-methoxyphenyl) methyl]-2,6-dioxo-3-piperidyl]trifluoromethanesulfonate (2.47 g, 6.47 mmol) in THF (20 mL) was added to the reaction mixture at 0-10 C. dropwise. The mixture was then stirred at 0-10 C. for another 30 minutes under N2. On completion, the reaction was quenched water (400 mL) and extracted with EA (3×200 mL). The combined organic layer was concentrated in vacuo. The residue was triturated with EA (80 mL) and filtered. The filter cake was collected and dried in vacuo to give the title compound (6.70 g, 67% yield) as light yellow solid. The filtrate was also concentrated in vacuo and the residue was purified by column chromatography to give another batch title compound (1.80 g, 18% yield) as light yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 7.47 (d, J=1.6 Hz, 1H), 7.21-7.16 (m, 3H), 7.01 (d, J=8.0 Hz, 1H), 6.85 (d, J=8.8 Hz, 2H), 5.55-5.51 (m, 1H), 4.84-4.73 (m, 2H), 3.72 (s, 3H), 3.33 (s, 3H), 3.04-3.00 (m, 1H), 2.83-2.67 (m, 2H), 2.07-2.05 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1632-83-3, name is 1-Methylbenzimidazole, 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 1632-83-3, Formula: C8H8N2

1-methylbenzimidazole (1 mmol, 132.1 mg)Perfluoroiodobutane (1.1 mmol, 380.5 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (1.2 mmol, 134.7 mg) is addedAnd 5mL of toluene,Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).2-Iodo-1-methylbenzimidazole was obtained (white solid, 208.9 mg, yield 81%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Liaoning University; Liang Fushun; Liu Xia; Han Zhengbo; Su Zhongmin; (10 pag.)CN107501023; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 36947-68-9, 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of corresponding 2-chloro-N-phenylacetamide (1 mmol), imidazole (1.5 mmol), N,N-diisopropylethylamine (0.35 ml, 2 mmol) in dimethylformamide (7mL) was stirred for 16 hours at 60C. Then the reaction mixture was cooled to roomtemperature and treated with water (35 ml). The crude product was filtered andpurified by recrystallization from acetonitrile or by HPLC chromatography (methanol/water). Yield: 15-70 % depending on the structures of the starting materials.

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-Isopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; SPRINGER, Wolfdieter; FIESEL, Fabienne C.; CAULFIELD, Thomas R.; (172 pag.)WO2018/23029; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem