Tag: M.W=100-200

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. 4331-29-7, name is 1H-Benzo[d]imidazol-7-amine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7N3

4-Chloro-6,7-dimethoxy-quinazoline (100 mg, 0.4500 mmol) and 1H-indazol-6-amine (59.27 mg, 0.4500 mmol) were mixed in MeCN (2 mL) and irradiated in a CEM microwave at 100 °C for one hour. The reaction mixture was allowed to cool and then passed through a short pad of silica. After concentration of the filtrate, the resultant solid was washed sequentially with acetonitrile and diethyl ether and dried in vacuo to give 16 (0.13g, 81percent) as a light brown solid. 1H NMR (DMSO-d6) delta 13.21 (br s, 1H), 11.37 (s, 1H), 8.84 (s, 1H), 8.30 (s, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.41 (d, J=8.6 Hz, 1H), 7.34 (s, 1H), 4.03 (s, 3H), 4.01 (s, 3H)

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 4331-29-7.

Reference:
Article; Jordan, Allan M.; Begum, Habiba; Fairweather, Emma; Fritzl, Samantha; Goldberg, Kristin; Hopkins, Gemma V.; Hamilton, Niall M.; Lyons, Amanda J.; March, H. Nikki; Newton, Rebecca; Small, Helen F.; Vishwanath, Swamy; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 11; (2016); p. 2724 – 2729;,
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. 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Butyl-2-methyl-1H-imidazole

General procedure: 1,2-Dimethyl imidazole (9.61 g; 0.10 mol) and trimethylphosphate (14.01 g; 0.10 mol) were mixed at room temperature under argon and vigorous stirring, then heated to 80C and stirred at this temperature for 1h. Acetonitrile (20 mL) was added and the mixture was stirred at 80C for 23h. The mixture was left at room temperature, the precipitate was separated,washed twice with acetonitrile and dried under vacuum (2 Torr) for 4 h at 80C.

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 13435-22-8.

Reference:
Article; Zicmanis, Andris; Anteina, Liene; Tetrahedron Letters; vol. 55; 12; (2014); p. 2027 – 2028;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53981-69-4,Some common heterocyclic compound, 53981-69-4, name is 1-(1H-Imidazol-2-yl)ethanone, molecular formula is C5H6N2O, 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 1-(3-bromopropyl)-4-chlorobenzene (1.5 g) and 2-acetylimidazole (0.87 g) in DMF (15 mL) was added potassium carbonate (3.6 g). The mixture was stirred for 1.5 hours at 70 C and allowed to cool to room temperature. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with brine three times and concentrated in vacuo onto ISOLUTE HM-N. The residue was purified with OH-type silica gel column chromatography (1-20 % MeOH in CHCI3) to give the title compound (Intermediate- 1, 1.6 g, 94 % yield) as light yellow oil. -NMR, MS and LCMS retention time data of Intermediate- 1 are shown in Table 1.

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; SASAKI, Toru; TANAKA, Nozomi; OTAKE, Norikazu; TSURUTA, Risa; YAMADA, Yousuke; MATSUDA, Yohei; OGATA, Yuya; (346 pag.)WO2018/216822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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 104619-51-4, Quality Control of Di(1H-imidazol-1-yl)methanimine

Step I: 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide, and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide (0386) Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-bromo-2-(1H-1,2,3,4-tetrazol-5-yl)-6-(trifluoromethyl)benzene-1-sulfonamide (230 g, 618.08 mmol, 1.00 equiv), potassium carbonate (276 g, 2.00 mol, 3.23 equiv), NaI (18.4 g), Bu4NCl (34.0 g, 122 mmol, 0.20 equiv), chloroform (3800 mL, 1.00 equiv), 1-(chloromethyl)-4-methoxybenzene (380 g, 2.43 mol, 3.93 equiv), water (2550 mL). The resulting solution was stirred for 12 hr at 55 C. The aqueous phase was extracted with 2×1000 mL of DCM. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/ hexane (1:10). Purification afforded 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide, and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide. (0387) LC-MS: (ES, m/z): 732 [M+H]+. (0388) H-NMR: (CDCl3, 300 Hz, ppm): delta 3.763 (9H, s), 3.820-3.872 (2H, d, J=15.6), 4.402-4.454 (2H, d, J=15.6), 5.154-5.203 (1H, d, J=14.7), 5.560-5.609 (1H, d, J=14.7), 6.702-6.763 (6H, m), 6.912-6.941 (4H, m), 7.109-7.138 (2H, m), 7.839-7.854 (2H, m). Reference Example 25 (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid and (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid Into a 1 L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide (REFERENCE EXAMPLE 24, 120 g, 163.81 mmol, 1.00 equiv), 1,4-dioxane (360 mL), 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (111 g, 491 mmol, 3.00 equiv), KOAc (80.3 g, 818 mmol, 5.00 equiv), 2-2-[chloro(triphenyl-5-phosphanylidene)palladio]phenylaniline (9.4 g, 16.42 mmol, 0.10 equiv). The resulting solution was stirred for 6 hr at 60 C. The resulting solution was diluted with 500 mL of CH3CN. The solids were filtered out. The filtrate was concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, CH3CN/H2O=1:2 increasing to CH3CN/H2O=2:1 within 25 min, and then CH3CN/H2O=2:1 within 25 min, and then CH3CN/H2O=1:0 within 10 min; Detector, UV 210 nm. This afforded (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid and (3-[bis[(4-methoxyphenyl)methyl]sulfamoyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-4-(trifluoromethyl)phenyl)boronic acid. (0391) LC-MS: (ES, m/z): 698 [M+H]+ (0392) H-NMR: (300 MHz, DMSO, ppm): delta 3.616-3.860 (11H, m), 3.860 (0.855H, s), 4.459-4.511 (1.492H, m), 5.172 (1.335H, s), 5.877 (0.403H, s), 6.733-6.827 (10H, m), 7.199-7.306 (2H, m), 8.456 (1.2H, m). Step B: 3-(2-amino-1H-imidazo[4,5-c]pyridin-7-yl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(2-amino-1H-imidazo[4,5-c]pyridin-7-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (1116) To a 10 mL sealed tube was added a solution of 3-(4,5-diaminopyridin-3-yl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(4,5-diaminopyridin-3-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (42 mg, 0.055 mmol) and di(1H-imidazol-1-yl)methanimine (8.90 mg, 0.055 mmol) in DMF (3 mL). The mixture was stirred for overnight at 120 C. The solvent was removed in vacuum and the residue was purified by column chromatography (ISCO RediSep Gold column 24 g) using 0-20% methanol/DCM as mobile phase to afford the title compounds. LC/MS (M+H)+: 786.68.

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, Di(1H-imidazol-1-yl)methanimine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4887-88-1,Some common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, molecular formula is C7H5BrN2, 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 above prepared 5-bromo-lH-benzo[d]imidazole (3.25 g, 22.1 mmol) in THF (65 mL) was added Boc20 (5.79 g, 26.5 mmol), Et3N (3.35, 33.15 mmol) and DMAP (270 mg, 2.21 mmol). The mixture was stirred at room temperature for 4 h, diluted with water (200 mL), extracted with ethyl acetate (200 mL). The organic layer was washed with water (2 x 100 mL) and brine (100 mL), dried over Na2S04, concentrated to give 0601-187 (4.8 g, 98%) as a oil. LCMS: 241 [M-55]+. 1H NMR (400 MHz, DMSO-<¾) delta 1.65 (s, 9H), 7.57 (dd, J; = 8.4 Hz, J2 = 20 Hz, 1H), 7.73 (d, J= 8.4 Hz, 1H), 7.88 (d, J = 9.2 Hz, 1H), 8.03 (d, J= 35.6 Hz, 1H), 8.70 (d, J= 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 5-Bromo-1H-benzo[d]imidazole, its application will become more common. Reference:
Patent; CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng; WO2011/130628; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, 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 23814-14-4, Quality Control of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

C) 2-Oxo-2, 3-dihydro-lH-benzoimidazolyl-5-carboxyl (I-N-3, 4- dibenzyloxy phenyl) amide; 1, 3- N, N-Diisopropylcarbodiimde (0.412 g; 3.27 mmol) was added to a solution of 2-oxo-2, 3-dihydro-1H-benzoimidazole-5-carboxylic acid (0.584 g; 3.27 mmol) 3,4-dibenzyloxy aniline (1.0 g, 3.27 mmol) and 1-hydroxybenzotriazole (0.442 g, 3.27 mmol) in anhydrous N, N – dimethylformamide (15 ml). After stirring for 16 hrs at room temperature the reaction mixture was poured in water (150 ml). The pH of the mixture was adjusted to 2 with IN hydrochloric acid and stirred for 30 minutes. Filtration and washing the product with ethyl acetate (3 x 10 ml) provided 1.12 grams of 2-Oxo-2, 3-dihydro-l H-benzoimidazolyl-5-carboxyl (1-N-3, 4-dibenzyloxy phenyl) amide. Yield = 73.6 %. ¹H NMR (CD3)2SO 10.5 (1H, s, NH) 7.65 (1H, d, J 8Hz) 7.6 (1H, s) 7.2-7.6 (m, 12H) 7.0 (2H, d, J 8Hz) 5.15 (4H, s).

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; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-42-2,Some common heterocyclic compound, 3034-42-2, name is 1-Methyl-5-nitroimidazole, molecular formula is C4H5N3O2, 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.

EXAMPLE 2 1-Methyl-2-hydroxymethyl-5-nitroimidazole 27.9 g. of 1-methyl-5-nitroimidazole prepared as in Example 1 and 30.1 g. of paraformaldehyde are added to 154 ml. of dimethylsulfoxide and the resulting solution is sealed into a glass-lined tube. The solution is heated at 110 C. for 24 hours, with shaking. The dimethylsulfoxide is removed by distillation at 53-56 C./2 mm. The residue is extracted with 3 * 150 ml. of hot benzene. The benzene extracts are combined and cooled to room temperature. 1-Methyl-2-hydroxymethyl-5-nitroimidazole crystallizes, and is recovered by filtration. The yield of product is 23 g., m.p. 112-114.5 C. When 1-ethyl-5-nitroimidazole, 1-propyl-5-nitroimidazole, 1-n-butyl-5-nitroimidazole, and 4(5)-nitroimidazole are used in the above reaction, respectively, the following compounds are prepared: 1-ethyl-2-hydroxymethyl-5-nitroimidazole; 1-propyl-2-hydroxymethyl-5-nitroimidazole; 1-n-butyl-2-hydroxymethyl-5-nitroimidazole; and 2-hydroxymethyl-5-nitroimidazole.

The synthetic route of 3034-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4010176; (1977); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, A common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

A solution of (4-(aminomethyl)phenyl)boronic acid hydrochloride (0.85 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.37 g), 4-bromo-1-methyl-1H-imidazole (0.80 g) and sodium carbonate (1.20 g) in DME (12 mL)-water (3 mL) was stirred under an argon atmosphere at 120C for 6 hr under microwave irradiation. To the reaction mixture was added 6N hydrochloric acid, and the mixture was washed with ethyl acetate. The aqueous layer was separated, neutralized with 8N aqueous sodium hydroxide solution, and concentrated under reduced pressure. The residue was washed with THF, and the obtained organic layer was concentrated. The residue was crudely purified by NH silica gel chromatography (hexane-ethyl acetate). The obtained crudely purified product was diluted with ethyl acetate, 4N hydrogen chloride ethyl acetate solution (1 mL) was added, and the resulting precipitate was collected by filtration, and dried to give the title compound (0.12 g). 1H NMR (300 MHz, DMSO-d6) delta 3.90 (3H, s), 4.05-4.10 (2H, m), 7.63 (2H, d, J = 8.3 Hz), 7.90 (2H, d, J = 8.3 Hz), 8.20 (1H, d, J = 1.1 Hz), 8.42 (3H, brs), 9.19 (1H, s), 1H not detected.

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); 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. 116568-17-3, name is 1H-Benzo[d]imidazole-6-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H7N3O

EXAMPLE 3 1-(6-Chloropyrazin-2-yl)-1H-benzimidazole-5-carboxamide and and A mixture of 2, 6-dichloropyraz’rne (2.0 g, 13. 4 mmol), 1H-benzimidazole-5-carboxamide (2. 0 g, 12.3 mmol) and cesium carbonate (5. 6, 17. 2 mmol) in DMF (10 mL) was heated at 90C for 3h. The solution was cooled to RT and diluted with ethyl acetate (20 mL) and filtered. The solid material was washed with chloroform-methanol (20mL, 4:1) and the combined flitrates (at) concentrated in vacuo. The residue thus obtained (3. 02 g) was used without further purification. m/z (EI) 273/275 (M+1)

According to the analysis of related databases, 116568-17-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/54230; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2301-25-9, 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 2301-25-9 as follows.

YB112 (162mg) was dissolved in THF solvent. After the reaction system was deaerated,10% Pd / C 20mg was added.A hydrogen balloon was added to the reaction system, and the reaction was allowed to proceed overnight.The reaction was filtered and washed with ethyl acetate, concentrated, and the target product YB126 (154 mg) was purified on a silica gel column.

According to the analysis of related databases, 2301-25-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem