Month: August 2021

Related Products of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-methyl-2-n-propyl-1H-benzimidazole-6-carboxylic (1, 2.18g, 10mmol) and thionyl chloride (20mL, 280mmol) was refluxed for 3h, then the excess thionyl chloride was removed under reduced pressure to obtain the crude acyl chloride (2) as an off-white solid. It was used for the next step directly.

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jun; Wang, Jin-Liang; Yu, Wei-Fa; Zhou, Zhi-Ming; Tao, Wen-Chang; Wang, Yi-Cheng; Xue, Wei-Zhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 44 – 54;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 137049-00-4, 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. 137049-00-4 name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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.

To methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate (Step 6, Example 1) (1.0 equiv) and Et3N (3.0 equiv) or pyridine (3.0 equiv) in CH2Cl2 (0.05 M) was added 1-methylimidazole-4-sulfonyl chloride (1.2 equiv). The reaction was monitored by TLC (10% MeOH-CH2Cl2) and was heated if necessary. After 30 min the mixture was poured into saturated sodium bicarbonate and extracted with CH2Cl2. The combined organic phase was washed with brine, dried over sodium sulfate and purified by column chromatography to afford 92% of the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-4-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2008/9485; (2008); A1;,
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 2034-22-2 as follows. Safety of 2,4,5-Tribromoimidazole

Step 1: N-(2.4.5-tribromo-l-(r2-(trimethylsilv?ethoxy1methyl|-lH-imidazole (A1); To a solution of 2,4,5-tribromo-imidazole in THF was added portionwise sodium hydride (1 eq.). The mixture was stirred for 20 min at RT and SEM-Cl (1 eq.) was added. The mixture was left stirring for 16 h at RT. After dilution with Et2O the suspension was filtered and the clear solution was concentrated to dryness under reduced pressure. The oily residue was dissolved in PE/ 5% EtOAc and applied on a silicagel column. After washing with PE/ 5% EtOAc the product was eluted with PE/ 10% EtOAc. The solvents were removed under vacuum to afford the title compound as a white solid. 1U NMR (400 MHz, CDCl3) delta: 5.31 (s, 2H), 3.59 (t, J=7.8 Hz, 2H), 0.92 (t, J=7.8 Hz, 2H), 0.01 (s, 9H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2008/56187; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application 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 7-1 (3.0 g, 7.0 mmol), benzimidazolo[1,2-a]benzimidazole (1.8 g, 8.4 mmol), and potassium phosphate (3.6 g, 29.8 mmol) were added to NMP (35 mL). The mixture was stirred at 190 C for 8 h. After reaction mixture was cooled at room temperature, it was diluted with 40 mL of water to give a solid. The solid was collected by filtration, and it was washed with 100 mL of water. The crude product was purified by by column chromatog20 raphy on silica gel eluting with toluene to yield 2.5 g (58%) of compound B-17 as a whitesolid. LC-MS (mlz) 615 [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 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

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 3034-50-2 as follows. Application In Synthesis of Imidazole-4-carbaldehyde

Example 63; (3H-Imidazol-4-ylmethyl)-(2-methoxy-phenyl)-amine; To a solution of 2-methoxyaniline (0.62 g, 5 mmol) in methanol (5 ml) was added 4- formylimidazole (0.48 g, 5 mmol). After stirring the mixture overnight at 600C the solution was cooled and sodium borohydride (0.28 g, 7.5 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by recrystallisation from heptane/ethyl acetate to yield off-white crystals (0.85 mg, 84%); MS (ISP): 204.3 ((M+H)+’).

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/46757; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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 precooled (0 C) solution of intermediate 2.55 (20. mg, 0.078 mmol) in dichloromethane (0.5 mL) was added triethylamine (30 muL, 0.2 mmol) and 1-methyl-1H- imidazole-4-sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 15 h, then diluted with wet DMSO (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (14 mg, 45% yield).1H NMR (500 MHz, Acetonitrile-d3) d 7.63 (d, J = 1.4 Hz, 1H), 7.56 (d, J = 1.4 Hz, 1H), 7.51 (t, J = 8.6 Hz, 1H), 7.11 (dd, J = 9.9, 2.6 Hz, 1H), 7.01- 6.95 (m, 1H), 3.75- 3.72 (m, 1H), 3.71 (s, 3H), 3.40 (dd, J = 12.3, 5.1 Hz, 1H), 3.10 (dd, J = 12.1, 9.1 Hz, 1H), 2.92 (tt, J = 9.0, 4.0 Hz, 1H), 2.81 (ddd, J = 12.9, 9.6, 3.4 Hz, 1H), 2.05- 1.97 (m, 1H), 1.87- 1.78 (m, 1H), 1.70- 1.56 (m, 2H); AMM 402.0697 (ESI) m/z [calc for C16H18ClFN3O4S (M+H)+ 402.0691].

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39513-26-3,Some common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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 stirred solution of 5-bromo-1H-benzo[d]imidazol-2(3H)-one (1.0 g,4.69 mmol)inTHF (10 mL)at 0 oc was added NaH (469 mg,11.74 mmol,60%)and the mixture was stirred10 for 30 min. Methyliodide (0.88 mL,14.08 mmol)was added dropwise and the mixture stirred atroom temperature for an additional 16 h. The mixture was quenched with saturated NH4Cl (20mL)and extracted with EtOAc (20 mL x 2). The combined organic layers were dried overanhydrous Na2S04,filtered and concentrated in vacuo. The crude residue was purified by silicagel chromatography (petroleum ether I EtOAc = 5: 1)to give the title compound (630 mg,56%)15 as a white solid. 1HNMR (400 MHz,CDCl3)8 7.23 (d,J= 8.4 Hz,1H),7.12 (d,J= 2.0 Hz,1H),6.84 (d,J= 8.4 Hz,1H),3.41 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,3-dihydrobenzoimidazol-2-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Commercially available (6-chloropyridin-3-yl)methanamine (1 g, 7 mmol) was dissolved in 40 ml of AcOEt and at OC triphosgene (1.93 g,7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10ml) of compound la (1 g, 6.7 mmol) and the mixture was warmed at 80C for8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1 X 40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 450 mg of a pale yellow solid. Yield = 21% ‘HNMR (DMSO, 200 MHz) delta 4.32 (2H, d, J = 5.8 Hz), 6.62 (1H, d, J = 7.2 Hz), 6.85 (3H, m), 7.48 (1H, d, J = 8.4 Hz), 7.81 (1H, dd, J = 8.2 Hz, J’ = 2.4 Hz), 8.33 (2H, m), 10.02 (1H, bs), 10.60 (1H, bs); [M+1] 317.8 (C14H12ClN5O2 requires 317.73).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
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. 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. Recommanded Product: 28890-99-5

A.) 20.0 g (87.3 mmol) 3-bromo-benzonitrile, 16.6 g (80.0 mmol) 6H-benzimidazolo[1 ,2- a]benzimidazole, 67.9 g (320 mmol) potassium phosphate tribasic, 1.5 g (7.88 mmol) cupper(l) iodide and 100 g (875 mmol) DACH ((±)-trans-1 ,2-diaminocyclohexane) in 240 ml dioxane are stirred at 100 C under nitrogen for 7 h. The reaction mixture is filtered hot and the solids are washed with dioxane. The reaction mixture is cooled to 50 C and the crystalized product is filtered of and is washed with methanol. Yield 1 1 .2 g (46 %) 1H-NMR (300 MHz, CDCI3): delta 7.33-7.49 (m, 4H), 7.59 – 7.63 (d, 1 H), 7.72-7.83 (m, 3H), 7.86- 7.90 (d, 2H), 8.22-8.26 (m, 2H),

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; RAIMANN, Thomas; SCHAeFER, Thomas; SAITO, Masatoshi; WOLLEB, Heinz; BENEDITO, Flavio Luiz; NISHIMAE, Yuichi; NAKANO, Yuki; NAGASHIMA, Hideaki; (111 pag.)WO2016/157113; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem