Category: imidazoles-derivatives

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

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

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

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

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

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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of Imidazole-4-carbaldehyde

Example 72An alternate method’for the synthesis of the imidazole intermediate is described below:4-Cyano-l-(2-trimethylsilanyl-ethoxymethyl)-lH-imidazole-2-carboxylic acid potassium salt a) lH-Imidazole-4-carbonitrile; ‘-NHA 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, a condenser, and an addition funnel with a nitrogen inlet was charged with lH-imidazole-4-carboxaldehyde (Aldrich, 1.10 kg, 11.5 mol) and pyridine (3.0 L, 3.0 mol). The reaction flask was cooled to 8 0C with an ice bath and hydroxylamine hydrochloride (871 g, 12.5 mol) was added slowly in portions to maintain the internal temperature below 30 °C. The reaction was allowed to cool to ambient temperature and stirred for 2 h at ambient temperature. The resulting thick yellow solution was heated to 80 0C with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise EPO over 200 min to maintain the temperature below 110 °C during the addition. The reaction mixture was heated at 100 0C for 30 min, after which time it was allowed to cool to ambient temperature and then further cooled in an ice bath. The pH was adjusted to 8.0 (pH meter) by the addition of 25 wt percent NaOH (5.5 L) at such a rate that the internal temperature was maintained below 30 °C. The reaction mixture was then transferred into a 22-L separatory funnel and extracted with ethyl acetate (6.0 L). The combined organic layer was washed with brine (2 x 4.0 L), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure at 35 °C to give the crude product as a yellow semisolid. The resulting semisolid was suspended in toluene (3.0 L) and stirred for 1 h, after which time it was filtered to give a light yellow solid, which was resuspended in toluene (3.0 L) and stirred for 1 h. The resulting slurry was filtered and the filter cake washed with toluene (2 x 500 mL) to give the title compound as a light yellow solid [870 g, 82percent). The 1H and 13C NMR spectra were consistent with the assigned structure.

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 3034-50-2.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
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