Author: Jessica.F

Electric Literature of 2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1H-benzo[djimidazole-2-carboxylic acid (161 mg, 990 imol, 1.2 eq) in 2 mL of DMF was added HATU (377 mg, 990imol, 1.2 eq) and TEA (167 mg, 1.6 mmol, 229 tL, 2.0 eq). The mixture was stirred at 15 Cfor 0.5 hour, then tert-butyl N-[(1R,3S)-3-(ethylamino)cyclohexylj carbamate, compound 2,(200 mg, 825 imol, 1.0 eq) was added and the resulting reaction mixture was stirred at 15 Cfor additional 15.5 hours. The reaction mixture was partitioned between 5 mL of water and 5 mL of ethyl acetate. The organic phase was separated, washed twice with 10 mL of brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give an oil. The oil was purified by prep-TLC (Si02, eluting with petroleum ether: ethyl acetate = 1:1) to give 150mg of compound 65 (388 imol, 47% yield) as a colorless gum.

The synthetic route of 1H-Benzimidazole-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 28890-99-5,Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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.

b) Compound 3-1 (1.55 g, 4.4 mmol), benzimidazolo[1,2-a]benzimidazole (960 mg, 4.6 mmol), and potassium phosphate (1.97 g, 9.3 mmol) were suspended in NMP (22 mL). The mixture was stirred at 190 Cfor 18.5 h. After the reaction mixture was cooled at roomtemperature, 44 mL of EtCH and 22 mL of water were added to the reaction mixture to give a solid. It was collected by filtration, and it was purifed by column chromatography on silica gel eluting with a mixed solvent of toluene and CHCI3.The product was further purified by recrystallization with toluene and cyclohexane to result in compound A-1O (yield: 1.55 g (65%)) as a white solid. LC-MS (mlz) 538.1HNMR (300 MHz, DMSO-c): 68.42-8.39 (m, 2H), 8.32-8.25 (m, 2H), 7.95-7.82 (m, 3H),7.72 (dd, J= 1.2, 7.6 Hz, 1H), 7.61-7.58 (m, 1H), 7.50-7.32 (m, 9H), 7.25 (t, J= 7.9 Hz,1H), 7.20-7.17 (m, 2H), 6.38 (dd, J= 1.1, 8.0 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 28890-99-5, 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16 a) 7.00 g (24.7 mmol) 1-bromo-4-iodo-benzene, 10.5 g (32.2 mmol) caesium carbonate, 2.36 g (12.4 mmol) copper(I) iodide and 2.85 g (24.7 mmol) L-proline are added to 5.13 g (24.7 mmol) mmol) 5H-benzimidazo[1,2-a]benzimidazole in 80 ml DMSO under nitrogen. The reaction mixture is stirred for 15 h at 100 C. and 4 h at 150 C., filtered on Hyflo with dichloromethane. The organic phase is washed with water. The organic phase is dried with magnesium sulfate. The product is decocted with diethylether and methyl ethyl ketone (MEK). Yield: 2.90 g (77%).1H NMR (400 MHz, DMF-d7): delta 7.93-8.10 (m, 4H), 7.78-7.92 (m, 2H), 7.72-7.79 (m, 1H), 7.49-7.71 (m, 1H), 7.31-7.49 (m 4H). b) The product of Example 16b) is prepared in analogy to the procedure described in Example 4b).1H NMR (400 MHz, DMF-d7): delta=8.19-8.33 (m, 10H), 7.83-7.87 (m, 2H), 7.73-7.77 (m, 2H), 7.35-7.54 (m, 4H). One signal is covered by DMF MS (APCI(pos), m/z): 565 (M+1).

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; BASF SE; US2012/241681; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 7098-07-9, 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. 7098-07-9, name is 1-Ethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of Zn(CH3COO)22H2O (0.1705 g, 0.8 mmol), NH4VO3(0.1404 g, 0.8 mmol), eIM (0.3 mL), and H2O (8 mL) was heated at about 120 ¡ãC for 72 h. After the mixture was cooled to room temperature, yellow crystals were isolated from the mixture.Yield: 76percent (based on NH4VO3); Anal. Calcd. for C30H48Zn2N12V4O12(percent): C, 32.63; H, 4.35; N, 15.23. Found: C, 32.76; H, 4.41; N, 15.21.

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

Reference:
Article; Niu, Yan-Hong; Yang, Song; Li, Ji-Kun; Xu, Yan-Qing; Hu, Chang-Wen; Chinese Chemical Letters; vol. 27; 5; (2016); p. 649 – 654;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 57531-38-1, name is 5-Chloro-4-nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C3H2ClN3O2

To a stirred solution of Imidazole compound in DCM (10.0 vol); DMAP and TEA were added at room temperature under nitrogen atmosphere and was kept for stirring for about 30 minutes, then compound-3 was dissolved in DCM (5.0 vol) and was added slowly to it and stirred for another 2.0 hrs. On completion of the reaction, the reaction mass was diluted with water. The layers were separated and aqueous layer was extracted twice with DCM (5.0 vol). The organic layer was washed with water and brine solution and dried over anhydrous Na2S04 under reduced pressure to get yield Compound-4 (Yield 75%).

The synthetic route of 57531-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KANDULA, Mahesh; WO2014/68506; (2014); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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. Computed Properties of C8H8N2O

To a solution of N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine (59 mg, 020 mmol) and l-methyl-2-benzimidazolinone (45 mg, 0.30 mmol) in dry pyridine (1 mL) was added potassium acetate (51 mg, 0.512 mmol), cuprous chloride (11.6 mg, 0.117 mmol), and copper powder (31 mg, 0.487 mmol). This mixture was sealed and heated at 120 C for 4 days. The cooled reaction was diluted with NaHCtheta3 solution and the product extracted into methylene chloride. This solution was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated This residue was subjected to chromatography on silica gel eluting with a 20-100% acetone/hexane gradient to give the title compound after trituration with diethyl ether as a white solid.IH-NMR (500 MHz, CDCl3): delta 8.54 (IH, d, J=3.7Hz), 8.36 (2H, v br s), 8.25 (2H, v br s), 7.95 (IH, d, J=7.3Hz), 7.33 -7.38 (3H, m), 7.27(1H, m), 7.18 -7.21 (2H, m) , 7.12 (IH, t, J=7.8Hz), 7.05-7.08 (2H, m), 5.36 (IH, v br s), 4.88 (IH, v br s), 3.47(3H, s). m/e (m+1): 409.2.

The synthetic route of 1-Methyl-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/89735; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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.

The amine precursor 16 (100,7 mg, 0.240 mmol, 1 eq.) was dissolved in 1 ml of DMF, acetylimidazole (31.7 mg, 0.288 mmol, 1.2 eq) and DIPEA (0.090 ml, 0.48 mmol, 2 eq.) wereadded to the solution. After stirring the mixture for 48h at room temperature, the solvent was evaporated under reduced pressure to give the corresponding crude, which was purified by HPLC using a gradient of 5percent to 95percent v/v acetonitrile in 0.1percent aqueous solution of formic acid to yield the titled compound. Yield: 91 mg, 0.187 mmol (78percent). 1H NMR (400 MHz, CDCI3) 9.25 (1H, 5), 8.70 (1H, 5), 7.97 (1H, t, J=6.5 Hz), 7.15 (1H, d, J=7.5 Hz), 6.83-6.80 (2H, m),6.72 (1H, d, J=8.8 Hz), 4.92-4.88 (1H, m), 4.57 (1H, 5), 4.52-4.42 (2H, m), 4.26-4.14 (2H, m), 3.59 (1H, dd, J=2.9, 11.1 Hz), 2.53-2.45 (4H, m), 2.24-2.17 (1H, m), 1.85 (3H, 5), 0.83 (9H, 5); 13C NMR (101 MHz, ODd3) O 171.8, 171.2, 155.9, 150.7, 148.1, 132.8, 131.7, 131.0, 124.2, 120.6, 117.1, 70.3, 58.1, 57.7, 57.1, 39.8, 35.5, 34.8, 26.3, 22.6, 16.0. HRMS (ESI) m/z: [M+H] calculated for: C24H32N405S: 488.21; observed: 484.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF DUNDEE; CIULLI, Alessio; MANIACI, Chiara; HUGHES, Scott J.; TESTA, Andrea; (111 pag.)WO2018/189554; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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 mixture of ethyl lH-imidazole-2-carboxylate (1.96 g, 14.0 mmol), 3,5-dichloro-2- fluoropyridine (1.80 g, 10.8 mmol), potassium carbonate (2.24 g, 16.2 mmol), and NMP (54 mL) was heated at 115 0C for 6 h, allowed to cool to rt, and then poured into EtOAc (200 mL). The mixture was washed with water (200 mL), washed with brine (200 mL x 2), dried, filtered, concentrated, and purified by silica gel chromatography (4:1–>1 :1; hexanes: EtOAc) to give ethyl l-(3,5-dichloropyridin-2-yl)-lH-imidazole-2- carboxylate. 1H NMR (400 MHz, DMSO-d6): delta 8.68 (d, IH), 8.62 (d, IH), 7.78 (d, IH), 7.36 (d, IH), 4.15 (q, 2H), 1.13 (t, 3H); LCMS: 286.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; KALYPSYS, INC.; WO2009/117421; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1450-93-7, A common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), molecular formula is C6H12N6O4S, 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.

1.1. 7-(pyrimidin-4-yl)-1 H-imidazo[1,2-a]pyrimidin-5-one A mixture containing 2.9g (15 mmol) of 3-oxo-3-(pyrimidin-4-yl)-propionic acid ethyl ester (prepared by analogy to the method described in patent DE 2705582), 2g (15 mmol) of 2-aminoimidazole hemisulfate and 1.2g (15 mmol) of ammonium acetate was heated at 140?C during 18 h. The cooled mixture was treated with 30ml of acetonitrile and filtered and the precipitate was added to water and heated at reflux temperature for 30 min. The resulting solution was cooled and the precipitate recovered by filtration. The crude product thus obtained was recrystallised from ethanol to give 1.75g of pure product as a gray solid. Mp: 345-346?C

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; SANOFI-SYNTHELABO; MITSUBISHI PHARMA CORPORATION; EP1340759; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2963-77-1, These common heterocyclic compound, 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, 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: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

The synthetic route of 2963-77-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; L’abbate, Fabrizio P.; Mueller, Ronel; Openshaw, Roxanne; Combrinck, Jill M.; de Villiers, Katherine A.; Hunter, Roger; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 243 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem