Tag: M.W=200-300

Synthetic Route of 870837-18-6, 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 870837-18-6 as follows.

General procedure: A suspension of indolinone (0.3mmol), aldehyde (0.3mmol) and pyridine (30muL) in methanol (1mL) were heated under microwave irradiation at 100 C for 30 minutes. The reaction mixture was cooled to room temperature and the resulting precipitate was removed by filtration, carefully washed with methanol and dried in vacuo. When no precipitate was observed methanol was removed under vacuum and the residue was purified by silica gel chromatography to give the desired product.

According to the analysis of related databases, 870837-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 305790-48-1, 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. 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 8 6-(3-chloro-phenyl)-1-methyl-1,3-dihydro-benzoimidazol-2-one Prepared from 1-methyl-6-bromo-1,3-dihydro-benzoimidazol-2-one and 3-chloro-phenyl boronic acid in the same fashion as that of Example 5. mp 219-220 C.; 1H-NMR (DMSO-d6) delta11.0 (s, 1H), 7.75 (bs, 1H), 7.65 (dd, 1H, J=7.5, 1.76 Hz), 7.49-7.44 (m, 2H), 7.39-7.32 (m, 2H), 7.06 (d, 1H, J=7.94 Hz), 3.35 (s, 3H); MS (ES) m/z 259([M+H]+, 100%); Anal. Calc. For C14H11ClN2O: C, 65; H, 4.29; N, 10.83. Found: C, 64.44; H, 4.36; N, 10.6.

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, 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6380235; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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. COA of Formula: C11H12N2O2

Step 4: 4-Amino-3-benzimidazol-2-yl-6-(4-methylpiperazinyl)hydroquinolin-2-one Ethyl 2-benzimidazol-2-ylacetate (1.1 equivalents) and 2-amino-5-(4-methylpiperazinyl)benzenecarbonitrile (1.0 equivalent) were dissolved in 1,2-dichloroethane, and then SnCl4 (11 equivalents) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NaOH (3 M) was added to the solid, and the mixture heated at 80 C. for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2Cl2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N) to give the desired product. LC/MS m/z 375.4 (MH+), Rt 1.65 minutes.

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

Reference:
Patent; CHIRON CORPORATION; US2005/256157; (2005); A1;; ; Patent; Chiron Corporation; US2005/261307; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2963-77-1, 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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Oxalyl chloride (191 muL) was added to a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (200 muL) in DCM (2 mL) and DMF (1 drop). After 1 hour, the reaction mixture was evaporated. A solution of 4-(1H-benzo[d]imidazol-2-yl)aniline (166 mg) and triethylamine (420 muL), in DCM (4 mL) was added to the initial reaction residue and stirred at ambient temp for 1 hour. The Reaction mixture was diluted with DCM and extracted sequentially with sat bicarb, water, brine, then dried over sodium sulfate, filtered and evaporated. The bis acylated material was purified on silica, eluting with a gradient of ethyl acetate (50-100%) in hexane. The pure bis acylated material was treated with ethylamine solution (2M in THF, 5 mL) for 18h. The reaction mixture was evaporated. Trituration with ethyl acetate / diethyl ether [1:4], afforded a solid which was collected by filtration (77mg, Y = 30%). UPLC-MS (Acidic Method, 4 min): rt 1.05 min, m/z 318.1 [M+H]+ 1H NMR (400 MHz, DMSO-d6) d ppm 12.83 (br s, 1H), 10.41 (s, 1H), 8.13-8.21 (m, 2H), 7.92 (d, J=8.8 Hz, 2H), 7.64 (br d, J=5.9 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.52 (br d, J=6.4 Hz, 1H), 7.19 (br d, J=4.3 Hz, 2H), 7.11 (d, J=2.0 Hz, 1H), 4.11 (s, 3H).

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, 4-(1H-Benzo[d]imidazol-2-yl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R.; GRAHAM, Mark; (46 pag.)WO2020/43880; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, 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 120781-02-4, SDS of cas: 120781-02-4

Methyl 2-(4-(hydroxymethyl)phenyl)-1-methyl-1H-imidazole-5-carboxylate (44). To a solution of methyl2-bromo-1-methyl-1H-imidazole-5-carboxylate5 (515 mg, 2.35 mmol, 1.0 eq) in dioxane (72 mL) was added Pd(PPh3)4 (133 mg, 0.115 mmol, 0.049 eq). The mixture was stirred for 15 min at room temperature before 4-hydroxymethylbenzeneboronic acid (357 mg, 2.35 mmol, 1.0 eq) in 22 mL H2O and K2CO3 (390mg, 2.82 mmol, 1.2 eq) were added. The reaction mixture was heated to 60 C and stirred for 16 h. The solvent was evaporated and the residue was diluted with EtOAc and H2O. The phases were separated and the product was extracted with EtOAc (3x 20 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (10-100% EtOAc linear gradient in hexanes) providing the corresponding benzylicalcohol in 81% (470 mg) yield.

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, Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fuerst, Rita; Yong Choi, Jun; Knapinska, Anna M.; Smith, Lyndsay; Cameron, Michael D.; Ruiz, Claudia; Fields, Gregg B.; Roush, William R.; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4984 – 4995;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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.

Take 250ml three mouth flask,The raw amine 3 (1.00 g, 4.15 mmol) was placed,20 ml of water was added,The temperature of the reaction system was lowered to 0 C,0.23 g of HCl was diluted in 5 ml of water and added dropwise to the reaction system,With the addition of HCl,The viscosity of the reaction system is increasing,So we carry out this step reaction is best to use mechanical stirring,After completion of the dropwise addition, stirring was continued at 0 C for 1 hour,Further, 20 ml of an aqueous solution of 0.28 g of sodium nitrite was added to the reaction system,Stirring was continued for 0.5 h.The above reaction solution system was added to KI (0.83 g) at 0 C,CuI (0.97 g) in 20 ml of water,Plus completed,The whole reaction system was gradually heated to 75 C,The reaction system has a bubble,Nitrogen gas is generated,When bubbles are no longer generated,To the reaction system, 50 ml of ethyl acetate was added to extract the product,The reaction process yield is not high,The reason for this is that the diazonium salts produced by Compound 3 are unstable,With the increase of temperature,Some of the diazonium salts have not decomposed before the iodide ion has been replaced.Too pure silica gel column,Compound 4 was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; Tianjin International Joint Academy of Biomedicine; Rao, Zihe; Yang, Cheng; Chen, Yue; Bai, Cuigai; Sun, Tao; Pan, Chengwen; Meng, Fanfei; Li, Yongtao; Wang, Jinghan; Jiang, Yin; (41 pag.)CN106188005; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 73746-45-9, A common heterocyclic compound, 73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, molecular formula is C4H5IN2, 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 160 mg (1.11 mmol) of 5-chloro-2-methyl-2H-pyridazin-3-one (CAS: [14628- 34-3]), 230 mg (1.11 mmol) of 4-iodo-2-methyl-lH-imidazole (CAS: [73746-45-9]), in 3.5 ml of dry DMF were added 721 mg (2.21 mmol) of cesium carbonate. The suspension was stirred for 30 min at 45C, then for 3h at 65C and allowed to cool. The cristallised product is filtered off, washed with ethyl acetate and dried in vaccuo to yield 250 mg (0.791 mmol, 71%) of the title compound as a crystalline light yellow solid, MS: m/e = 316.9 (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; F. HOFFMANN-LA ROCHE AG; JAESCHKE, Georg; LINDEMANN, Lothar; VIEIRA, Eric; WICHMANN, Juergen; WO2011/6910; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-16-5,Some common heterocyclic compound, 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, molecular formula is C8H7BrN2, 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 intermediate 5 (2.5g, 11.8 mmol) in dioxane (100ml) were addedtributyl(vinyl)tin (5,2ml, 18 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.69g, O.Smmol) and the mixture was heated under reflux for 24 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2CI2/MeOH (95/5). The title compound was obtained as an oil (1.8g, 96.1percent); NMR H1 (300MHz, CDCI3, ppm) 5: 7.9 (s, 1H), 7.75 (d, 1H), 7.4 (m, 2H), 6.85 (dd, 1H), 5.8 (d, 1H), 5.25 (d, 1H), 3.85 (s, 3H).

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]imidazole, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/111046; (2004); A2;,
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. 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1H-Benzo[d]imidazole-5,6-dicarboxylic acid

Step A: 5,6-di-(methoxycarbonyl)-benzimidazole To a solution of 200 mg of 5,6-benzimidazoledicarboxylic acid dissolved in 2.0 mL of MeOH and 2.0 mL of diethyll ether was added 4 mL of trimethylsilyldiazomethane [2.0 M in hexanes]. The resulting solution was stirred for 1 hour before dilution with 20 mL of H2O and extraction with 2*10 mL of EtOAc. the organic phases were dried over MgSO4 and concentrated under reduced pressure. Column chromatography (SiO2, 5% MeOH in CH2Cl2) yielded 210 mg of the title compound as a yellow oil. Mass Spectrum (ESI) 231 (M+1).

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 10351-75-4.

Reference:
Patent; Merck & Co., Inc.; US6498165; (2002); B1;,
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 152628-03-0 as follows. category: imidazoles-derivatives

Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid 50.0g (229mmol) and polyphosphoric acid added and stirred and 300 g, heated to around 70 C., the reaction solution obtained was stirred for 30 minutes, added in portions over a period N- methyl -O- phenylenediamine 45.0g of (368mmol) 2 hours It was.After adding the entire amount, stirring for 1 hour at around 70 C., and stirred for 5 h warmed to near yet 130. C..After confirming the disappearance of 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid by HPLC, was cooled to about 70 C., while maintaining the water 600g The temperature of the reaction solution at 70 to 85 C. It was dropped little by little.After the total amount dropwise, 30 C. and cooled to near, pH of the reaction solution with aqueous ammonia was adjusted to be pH 8.3, after stirring for 1 hour warmed to around 50 C., the solid by vacuum filtration It is filtered off and washed the solid was filtered off with water 200g in the vicinity of 50 , to obtain a wet product of light brown crystals.Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, was added and stirred the wet product of the resulting pale brown crystals and water 900 g, after stirring for 1 hour warmed to around 50 C. , vacuum filtered off the solids by filtration, wash the solid was filtered off with 100g of water around 50 C., the resulting wet product was dried for 15 hours under reduced pressure, a pale crude benzimidazole body as brown crystals to obtain a body 60.3g.The crude product of the benzimidazole body was analyzed by HPLC, the purity was 98.20%, the content of methyl benzimidazole body 0.14%, the content of ethyl benzimidazole body with 0.07% there were. stirring blade, a thermometer, three-necked flask 100mL fitted with a condenser, a mixture of a crude product 5.0g of methanol 12g and water 50g benzimidazole body obtained in Production Example 1 was added after stirring on, the addition of hydrochloric acid 2.1g containing hydrogen chloride 0.78 g (21.4 mmol), stirred for 10 minutes at about 25 C., the solid in the reaction solution was confirmed to be dissolved.Then, was added aqueous ammonia 1.1g containing ammonia 0.28 g (16.5 mmol), precipitation of white crystals was confirmed.After stirring for 1 hour at about 25 C., vacuum filtered through the solid was filtered off, the solid was filtered off with water 5g were washed twice and dried for 12 hours at 60 C. under reduced pressure and the resulting wet biomass, to obtain a benzimidazole body 4.2g (13.9mmol) as white crystals.Recovery rate, which is calculated based on the mass of the crude product of the benzimidazole body was 84.4%.As a result of the benzimidazole body obtained was analyzed by HPLC, the purity was 99.56%, the content of methyl benzimidazole body 0.06%, the content of ethyl benzimidazole body 0.02% met.

According to the analysis of related databases, 152628-03-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKUYAMA CORPORATION; MIYAOKU, TAKAYUKI; (16 pag.)JP2015/160810; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem