Month: July 2021

2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 2466-76-4

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0, 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 2620-76-0 as follows.

Example 5In Example 5, an example of a synthesis method of 4-(9H-carbazol-9-yl)-4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)triphenylamine (abbreviation: YGABIm) which is represented by a structural formula (227) will be described. A synthesis scheme is shown in the following (E5-1). In a 100 mL three-necked flask were placed 1.0 g (2.7 mmol) of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d]imidazole, 0.96 g (2.7 mmol) of 4-(carbazol-9-yl)diphenylamine (abbreviation: YGA), 0.60 g (6.3 mmol) of sodium tert-butoxide, and 0.050 g (0.086 mmol) of bis(dibenzylideneacetone)palladium(0), and the atmosphere in the flask was replaced with nitrogen.To this mixture were added 15 mL of toluene and 0.050 mL of a 10percent hexane solution of tri(tert-butyl)phosphine. This mixture was stirred at 80° C. for 5 hours. After the stirring, toluene was added to this mixture, and this suspension was subjected to suction filtration through Celite to give a filtrate. The obtained filtrate was washed with water, a saturated sodium hydrogen carbonate solution, and a saturated saline solution in this order. Then, the organic layer and the aqueous layer were separated, and magnesium sulfate was added to dry the organic layer. This mixture was subjected to suction filtration so that the magnesium sulfate was removed to give a filtrate. The obtained filtrate was concentrated to give a compound. The obtained compound was purified by silica gel column chromatography. The silica gel column chromatography was performed by, first, using toluene as a developing solvent, and then using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=5:1) as a developing solvent. The obtained fraction was concentrated to give a compound. The obtained compound was recrystallized with a mixed solvent of chloroform and hexane to give 1.2 g of a light yellow powdered solid in a yield of 74percent.Then, 1.2 g of the obtained solid was sublimated and purified by train sublimation. The sublimation purification was performed under a reduced pressure of 2.7 Pa, with a flow rate of argon at 5 mL/min, at 261° C., and for 14 hours. After the sublimation purification, 1.0 g of a target substance was obtained in a yield of 83percent.By a nuclear magnetic resonance (NMR) method, this compound was confirmed to be 4-(9H-carbazol-9-yl)-4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)triphenylamine (abbreviation: YGABIm), which was a target substance.1H NMR data of the obtained compound is shown below: 1H NMR (CDCl3, 300 MHz): delta=7.30-7.56 (m, 27H), 7.87 (d, J=8.3 Hz, 1H), 8.13 (d, J=7.8 Hz, 2H)

According to the analysis of related databases, 2620-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US8329917; (2012); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 405173-97-9, 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 405173-97-9 as follows.

General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 – 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 – 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion to general procedure 7, 2-(2-aminoethyl)-N-(pyridin-2-ylmethyl)-1 ,3-thiazole-4- carboxamide dihydrochloride (105) (240 mg, 0.72 mmol), 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole (259 mg, 1 .43 mmol) and DIPEA (2.17 ml, 12.53 mmol) in DMF (10 ml) afforded the title compound (64 mg, 22%) as a brown solid after purification by basic prep-HPLC followed by flash column chromatography (eluting with a gradient of 0-10% MeOH / DCM followed by 0.8 M ammonia in MeOH / DCM) 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 8.87 (t, J = 6.0 Hz, 1 H), 8.50 (d, J = 4.6 Hz, 1 H), 8.10 (s, 1 H), 7.74 (td, J = 7.7, 1 .7 Hz, 1 H), 7.44 (s, 2H), 7.33 – 7.21 (m, 2H), 7.10 (dd , J = 5.9, 3.2 Hz, 2H), 4.55 (d , J = 6.0 Hz, 2H), 3.15 (t, J = 6.7 Hz, 2H), 3.02 (t, J = 6.7 Hz, 2H), 2.90 – 2.96 (m, 4H) HPLCMS (Method G): [m/z]: 407.2 [M+H]+

According to the analysis of related databases, 405173-97-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); 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. 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., Product Details of 17228-38-5

To a solution of N-methyl-1H-benzimidazol-2-amine (1.36 g, 9.24 mmol, 1.00) in acetonitrile (40 mL) was added cesium carbonate (12 g, 37.0 mmol, 4 equiv) followed by methyl 4-bromobutanoate (1.40 mL, 2.01 g, 11.1 mmol, 1.0 equiv). The reaction mixture was stirred overnight at RT, then was filtered through Celite and concentrated to dryness in vacuo. The residue was purified by flash column chromatography (silica gel, 100-200 mesh, 0 to 10% methanol in dichloromethane) to afford methyl 4-[2-(methylamino)benzimidazol-1-yl]butanoate (0.65 g, 28%) as an orange oil. LCMS (5 to 95% acetonitrile in water + 0.1% formic acid over 2 mins) retention time 0.88 min, ESI+ found [M+H]

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; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., COA of Formula: C7H7N5

To a stirred solution of 2-amino-4- (pentafluorosulfanyl) phenol (40) (70 mg, 0.30 mmol) in CH 3CN (1 mL) was added di (1H-imidazol-1-yl) methanimine (96 mg, 0.60 mmol) in one portion at 20 . The reaction mixture was stirred at 80 for 6 h. The solvent was evaporated and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10: 1-2: 1) to afford the titled compound IV (56 mg, 72) as a white solid. [0347] 1H NMR (400MHz, DMSO-d6) delta 7.85 (s, 2 H) , 7.68 (s, 1 H) , 7.52 (s, 1 H) [0348] MS (ESI) : [M+H +] 260.8.

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; XW LABORATORIES INC.; XW LABORATORIES, INC.; XIANG, Jia-Ning; XU, Xuesong; ZHOU, Wei; (123 pag.)WO2018/176343; (2018); A1;,
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. 1544-75-8, name is 5-Fluoro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1544-75-8

Obtained through a method the N- acetyl benzylamine piperazine (II) intermediate (19. 6mmol), an alcoholic solution of formaldehyde (16. 3mmol), 5- fluoro-1,3-dihydro-benzimidazol-2-one (16. 3mmol) into 30ml of absolute ethanol, at room temperature for 15h. The reaction was concentrated under reduced pressure to give a crude oil. The crude product was purified by silica gel column chromatography to obtain the free base of N- benzyl-2- {4 – [(5-fluoro-2-oxo-2,3-dihydro-benzo -111- [(1] imidazol-1 yl) methyl] piperazin-1-yl} acetamide (V_19), 4.67g, yield 72.1%.

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; Shanghai Pharmaceutical Industry Research Academy; China State Institute of Pharmaceutical Industry; Li, Jiangqi; Weng, Zhije; Cui, Ning; Jie, Peng; Ma, Xiao; (25 pag.)CN105418506; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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 solution of tert-butyl (6-(3-((6-amino-,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate (67 mg, 0.12 mmol) in DCM (2 ml) were added 1-methyl-1H-imidazole-4-sulfonyl chloride (46 mg, 0.26 mmol) and pyridine (100 muL, 1.24 mmol), the sulfonyl chloride was not fully soluble, so dioxanes (2 mL) was added and the resulting mixture was stirred at 60 C. for 21 h. The resulting suspension was concentrated, then purified by silica-gel chromatography (1:5-1:1 EtOAc/hexanes then 100% EtOAc) and dried to give tert-butyl (6-(3-((1,3-dimethyl-6-(1-methyl-1H-imidazole-4-sulfonamido)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)oxy)-5-propoxyphenoxy)hexyl)carbamate as a red-colored amorphous solid (58 mg, 68%). MS (ES+) C33H46N6O8S requires: 686. found 687 [M+H]+. 1H NMR (600 MHz, CDCl3) delta: 7.97 (br-s, 1H), 7.60 (s, 1H, overlapped with CHCl3), 7.35 (s, 1H), 7.31 (s, 1H), 7.20 (s, 1H), 6.57 (s, 1H), 6.14 (s, 1H), 5.77 (br-s, 1H), 5.72 (br-s, 1H), 3.86 (t, J=6.4 Hz, 2H), 3.83 (t, J=6.5 Hz, 2H), 3.62 (s, 3H), 3.45 (s, 3H), 3.31 (s, 3H), 3.12 (br-t, J=6.3 Hz, 2H), 1.76 (m, 4H), 1.51 (m, 2H), 1.46 (m, 2H), 1.44 (s, 9H), 1.37 (m, 2H), 1.01 (t, J=7.3 Hz, 3H).

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; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of cucurbiturils was prepared by preparing a solution of glycoluril (111 g, 0.781 moles) in water (123 ml, 6.833 moles) under stirring. Sulphuric acid (125 mL, 2.34 moles) and formalin (116 mL, 1.56 moles) were added to the solution of glycoluril and the mixture heated to 100C and held under stirring for 14 hours. The reaction mixture was then cooled to room temperature over a 3 hour time period and the cooled reaction mixture precipitated into methanol (1000 ml). The precipitate was filtered, slurried with methanol (1000 ml), filtered again and dried. (0047) The mixture was determined using nuclear magnetic resonance (1H NMR) imaging to be 20- 25 percent by weight CB[5], 45-55 percent by weight CB[6], 20-25 percent by weight of CB[7], 5-8 percent by weight of CB[8], and less than 1 percent by weight CB[9] and higher cucurbiturils, based on the total weight of cucurbituril in the mixture

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, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; CHEESMAN, Ben; ZHANG, Jing; (20 pag.)WO2018/178647; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 60-56-0,Some common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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 mixing of thiols (1 mmol), sodium hydroxide(1.1 mmol), water (0.5 mL) and methanol (3 mL) were stirred in room temperature. After 30 min,compound 2 (1.1 mmol) in 5 mL CH2Cl2 was added dropwise to the mixture for 36 h-42 h. The mixturewas concentrated in vacuo. The residue was dissolved by CH2Cl2. The solution was extracted threetimes with water. The organic phase was dried overnight with anhydrous sodium sulfate. The solventwas concentrated in vacuo to give crude products. The crude product was purified by silica gelcolumn chromatography.

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-1H-imidazole-2(3H)-thione, its application will become more common.

Reference:
Article; Yi, Yunpeng; Fu, Yunxing; Dong, Pengcheng; Qin, Wenwen; Liu, Yu; Liang, Jiangping; Shang, Ruofeng; Molecules; vol. 22; 6; (2017);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

4-(Trifluoromethyl)-1 /-/-imidazole (640 mg, 4.7 mmol) was stirred in dry THF (30 ml_) at room temperature under nitrogen. Lithium hexamethyldisilazide (1 M in THF, 4.2 ml_, 4.2 mmol) was added. After 45 minutes, a solution of Intermediate (1-13b) (1.42 g, 4.7 mmol) in dry THF (20 ml_) was added. The reaction was stirred for 12 hours. The reaction was quenched with saturated ammonium chloride and diluted with brine and ethyl acetate. Enough water was added to dissolve the precipitated salts. The aqueous layer was extracted with ethyl acetate, and the combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 100% heptane gradient to 80% ethyl acetate/heptane. The appropriate fractions were combined, evaporated, and dried under high vacuum to afford (1-13c) as a yellow oil (689 mg, 2.39 mmol, 57%). m/z 289.2 (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 4-(Trifluoromethyl)-1H-imidazole, its application will become more common.

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem