Month: June 2021

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: 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

Application of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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.

Example 1: To the reaction portion were added 85 g of ethyl 4- (1-hydroxy-1-methylethyl) -2-propyl-imidazole-5-carboxylate (Formula 2), 4- [2- (trityltetrazol- ) Phenyl] benzyl bromide (Formula 3), 32.4 g of potassium tertiary phosphate (K3PO4) and 600 mL of N, N-dimethylacetamide were added and the mixture was stirred at a temperature of 60 to 65 DEG C for 6 hours. Then, the mixture was stirred for 1 hour while gradually adjusting the temperature to 25 to 30 . 400 mL of ethyl acetate was added to the reaction solution, and 1 L of purified water was slowly added dropwise over 30 minutes while stirring, and crystals were precipitated. The resulting crystals were stirred at 25 to 30 DEG C for 2 hours, filtered and washed with 1 L of purified water and then dried at 55 to 60 DEG C for 12 hours to obtain ethyl 4- (1-hydroxy-1-methylethyl) 226 g (yield 89.3%, purity 99.95%) of 1- {4- [2- (trityltetrazol-5-yl) phenyl] phenyl} -methylimidazole-5-carboxylate .

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONGBANG FTL CO., LTD; Song, Tae Hong; Jung, Hun Suk; Jang, Do Yeon; Moon, Chung Sun; Jung, Hee Jung; (18 pag.)KR101526249; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2034-22-2, 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. 2034-22-2, name is 2,4,5-Tribromoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure for the synthesis of AB1 To a stirred solution of 2,4,5-tribromoimidazole (1.0 g, 3.28 mmol) in tetrahydrofuran (15.0 mL) was added NaH (60% dispersion in paraffin, 0.20 g, 4.92 mmol) under ice-bath. After 10 min, chloromethyl methyleter (0.30 mL, 3.94 mmol) was added slowly. The reaction mixture was allowed to room temperature and further stirred for 1.5 hours. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (20 mL x 2). The organic layer was dried over anhydrous MgS04 and concentrated in vacuo to give AB1.

The synthetic route of 2,4,5-Tribromoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT PASTEUR KOREA; TERRAMARK MARKENCREATION GMBH; KIM, Jaeseung; KANG, Sunhee; KANG, Juhee; LEE, Sumi; SEO, Jeong Jea; SEO, Mooyoung; (156 pag.)WO2015/193506; (2015); A1;,
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

Related Products of 86604-86-6, A common heterocyclic compound, 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, molecular formula is C8H4ClF3N2, 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.

33 mg (0.11 mmol) 4-(3-Amino-benzylamino)-quinazoline-8-carboxylic acid amide hydrochloride and 24 mg (0.11 mmol) 2-Chloro-5-trifluoromethyl-1 H-benzoimidazole were dissolved in 500 mul DMF and stirred at 100C for 15 h. The reaction mixture was directly purified using preparative HPLC. The product was treated with HCI in methanol and concentrated in the SpeedVac.11.0 mg, off-white solid. Rt. = 2.15 min (method C), LCMS: 478 (M+H).Product is the hydrochloride salt.1H NMR (500 MHz, DMSO) delta 10.99 (b, 2H), 8.89 (d, J = 7.9, 1 H), 8.82 (s, 1 H), 8.56 (d, J = 7.0, 1 H), 8.16 (d, J = 5.5, 1 H), 7.88 (t, J = 7.9, 1H), 7.72 (s, 1 H), 7.57 (s, 1H), 7.55 -7.39 (m, 5H), 7.31 – 7.19 (m, 1 H), 5.01 (d, J = 5.6, 2H).

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; MERCK PATENT GMBH; SUTTON, Amanda E.; RICHARDSON, Thomas E.; HUCK, Bayard R.; KARRA, Srinivasa R.; CHEN, Xiaoling; XIAO, Yufang; GOUTOPOULOS, Andreas; LAN, Ruoxi; PERREY, David; VANDEVEER, Harold, George; LIU-BUJALSKI, Lesley; STIEBER, Frank; HODOUS, Brian L.; QIU, Hui; JONES, Reinaldo C.; HEASLEY, Brian; WO2010/93419; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, These common heterocyclic compound, 288-32-4, name is 1H-Imidazole, 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 imidazole 9A (20 g, 294 mmol) in THF (200 mL) and TEA (40 g, 400 mmol) was added dimethylsulfamoyl chloride (55 g, 383 mmol) slowly at 0 C. The mixture was stirred at room temperature overnight. The reaction mixture was poured into 300 mL of water and extracted with ethyl acetate (3x). The solution was washed with water and brine, dried over Na2S04, then concentrated to dryness to give compound 9B (42 g, 89%) as a colorless oil, which solidified after standing at room temperature for 1 h. The solid material was used directly in the next step without further purification. 1H NMR (400 MHz, CDC13) delta 7.86 (s, 1H), 7.23 (s, 1H), 7.11 (s, 1H), 2.82 (s, 6H).

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROPORE THERAPIES, INC.; STOCKING, Emily, M.; WRASIDLO, Wolfgang; WO2015/116663; (2015); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C4H4N2O

Synthesis of 1-Trityl-1H-imidazole-4-carbaldehyde STR49 To dimethylformamide (100 mL) was added imidazole-4-carboxaldehyde (10 g, 0.104 mol, Aldrich Chemical Corp.) and triethylamine (20.5 mL, 0.147 mol). A solution of trityl chloride (40 g, 0.143 mol) in dimethylformamide (300 mL) was added, followed by stirring at 25 C. for 6 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (1.5 L) and 1N citric acid (350 mL). The phases were separated, and the organic phase was washed with brine, dried over anhydrous magnesium sulfate, and filtered. Concentration of the solution in vacuo gave a white solid, 27.59 g, 78% yield. NMR was consistent with structure. MS: APCI: M-1: 337.2 (M: 338.41).

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; Warner-Lambert Company; US6143766; (2000); A;,
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

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