Month: September 2021

1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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. Formula: C29H22N2O

In the atmosphere of nitrogen and ice bath conditions,Will be 60% sodium hydride (38 mg, 0.97 mmol, 1.0 equiv)Dissolved in 15 ml of tetrahydrofuran,(2-(7-Fluorobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-14) (278 mg, 0.97 mmol, 1.0 equiv) was slowly addedTetrahydrofuran solution (15 ml).After stirring the mixture for 15 minutes,2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (402 mg, 0.97 mmol, 1.0 equiv)A solution of tetrahydrofuran (20 ml) was added dropwise thereto.The mixture was stirred at ice bath for 0.5 hours.The reaction was warmed to room temperature and stirred overnight. After the reaction is completed, quench with saturated aqueous ammonium chloride, dichlorineMethane was extracted and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a yellow oil. The result isPurification by silica gel column chromatography (eluent: ethyl acetate/petroleum ether = 1/2) yields the desired product 1-(7-fluorobenzofuran-5-Radyl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (252 mg, yield: 45.2%) wasYellow oil.

The synthetic route of 1402838-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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 670-95-1 as follows. Safety of 4-Phenylimidazole

3.04 g (20 mmol) of 4-(hydroxymethyl)phenylboronic acid, 1.44 g (10 mmol) of 4-phenylimidazole, 2.8 ml (20 mmol) of triethylamine and 1.64 ml (20 mmol) of pyridine are dissolved in 20 ml of dimethylformamide. 2.72 g (15 mmol) of copper diacetate are added and the mixture is stirred for 24 hours at ambient temperature. It is diluted with 200 ml of dichloromethane and 200 ml of aqueous 28% ammonia solution. After the phases have settled and been separated, the aqueous phase is extracted with 100 ml of dichloromethane. The organic phases are washed with 50 ml of saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 97/3 then 95/5 mixture of dichloromethane and methanol. The product is recrystallized from a mixture of toluene and diisopropyl ether, to give 1.82 g of product in the form of white crystals. Melting point ( C.): 137-139

According to the analysis of related databases, 670-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sanofi-Aventis; US2006/14830; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 52099-72-6

To a solution of 1-isopropenylbenzimidazolone (220 mg, 1.3 mmol) in dry THF (10 inL) are added triphenylphosphine (397 mg, 1.5 mmol) and (l,2-Dimethyl-lH-indol-7-yl)-methanol (220 mg, 1.3 mmol). Then diisopropyl azodicarboxylate (0.31 mL, 1.5 mmol) is added drop wise into the above solution at room temperature. The mixture is stirred for 16 hrs and then the solvent is removed under vacuum. The residue is purified by flash column chromatography using 10-30% EtOAc in hexanes to give 200 mg (48%) of l-(l,2-dimethyl-lH-indol-7-ylmethyl)-3- isopropenyl-l,3-dihydro-benzimidazol-2-one.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-13-3, 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 641571-13-3 as follows.

To a solution of 4-methyl-N3-[l-(7Eta-rhoyrrolo[2,3-J]pyrimidin-4-yl)-lEta- imidazol-2-yl] -benzene- 1,3 -diamine (15.0 mg, 0.049 mmol), 3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-benzoic acid (16.0 mg, 0.059 mmol), and DIEA (35yL, 0.20 mmol) in DMF (2mL) is added HATU (21 mg, 0.055 mmol). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (ImL). The resulting solution is subjected to purification by reverse-phase HPLC to give 3-(4-methyl- EPO imidazol-l-yl)-N-{4-methyl-3-[l-(7H-pyrrolo[2,3-cT]pyrimidm-4-yl)-lH-imidazol-2- ylamino]-phenyl}-5-trifluoromethyI-benzamide: 1H NuMR 600 MHz (DMSO-J6) delta 12.73 (s, IH), 11.32 0, IH), 10.67 (s, 1 H), 9.60 (s, 1 H), 8.82 0,1 H), 8.64-8.56 (m, 2H), 8.46 (s, IH), 8.43 (s, IH), 8.17 (s, IH), 7.93 (d, IH, J= 2.8 Hz), 7.79 (t, IH, J= 3.2 Hz), 7.52 (d, IH, J= 8.0 Hz), 7.30 (J, IH, J= 8.0 Hz), 7.11 (s, IH), 7.07 (m, IH), 2.39 (s, 3H), 2.36 (5, 3H); MS m/z 558.2 (M + 1).

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2006/101783; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 177843-26-4, name is 4-Bromo-1H-benzo[d]imidazol-5-amine, 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 177843-26-4, SDS of cas: 177843-26-4

5-(methylthio)-3,4-dihydro-2H-pyrrole (238mg) was combined with of 1 H-benzimidazol- 6-amine, 7-bromo (430 mg) (CAS 177843-26-4) in 10 mL of isopropyl alcohol. The reaction was stirred at reflux for 4 days. The refluxed mixture was then cooled to room temperature and concentrated. Flash column chromatography (4-6% 7N NH3 in MeOH/DCM) yielded the title compound 1 H NMR (300 MHz, CD3OD) delta 2.08 (m, 2H), 2.55 (t, J=7.92Hz, 2H), 3.39 (t, J=6.74Hz, 2H), 6.93 (d, J=8.50Hz, 1 H), 7.50 (d, J=8.50Hz, 1 H), 8.1 1 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1H-benzo[d]imidazol-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; CHOW, Ken; GIL, Daniel W.; DONELLO, John E.; WANG, Liming; CORPUZ, Evelyn G.; FANG, Wenkui K.; SINHA, Santosh C.; DIBAS, Mohammed I.; WO2011/44229; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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 solutionof amine 3-(4-methyl-1H-imidazol-1-yl)-5-(triuoromethyl)aniline (a) (one equivalent) and Et3N(1.5 equivalents) in dry CHCl3 cooled to 0 C was added dropwise to a solution of4-(chloromethyl)benzoyl chloride (4) (one equivalent) in dry CHCl3. The reaction mixture wasstirred at room temperature. The progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated, and the water layer was extracted by CHCl3 threetimes. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum.The product was purified by column chromatography on silica gel. The white solid 5 was given with 60% yield; m.p. 80-82 C; 1H-NMR (DMSO-d6, 500 MHz) : 10.74 (s, 1H), 8.32 (s, 1H), 8.26 (d,J = 1.0 Hz, 1H), 8.17 (s, 1H), 8.03 (d, J = 8.3 Hz, 2H), 7.77 (s, 1H), 7.66 (d, J = 8.0 Hz, 2H), 7.52 (s, 1H),4.89 (s, 2H), 2.21 (s, 3H); 13C-NMR (DMSO-d6, 125 MHz) : 166.1, 142.2, 141.7, 139.4, 138.4, 135.5, 134.4,129.4, 128.6, 115.4, 114.7, 112.2, 45.8, 14.0; HRMS (ESI+) m/z calculated for C19H16ClF3N3O [M + H]+394.0929, found 394.0927; purity: 97.93% (by HPLC).

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1964-77-8

1. To a solution of 5-bromo-2-methyl-lH-benzo[d]imidazole (422 mg, 2.00 mmol) in 20 mL of THF, was added 4.1 mL of t-BuLi solution in hexanes (1.6 M) at -78 C. After 1 hr, a solution of 5-methoxy-l-(phenylsulfonyl)-lH-indole-2-carbaldehyde (693 mg, 2.20 mmol) in 10 mL of THF was added slowly. After 2hr, the reaction mixture was allowed to warm up to RT slowly, quenched with saturated ammonium chloride solution, and extracted with EtOAc. The organic layer was washed with brine, dried (MgS04), and concentrated to give impure (5- methoxy-l-(phenylsulfonyl)-lH-indol-2-yl)(2-methyl-lH-benzo[d]imidazol-5-yl)methanol, which was dissolved in 20 mL of dichloromethane and 20 mL of THF, and reacted with Mn02(3.50 g, 40.0 mmol) overnight at RT. The reaction mixture was diluted with EtOAc, filtered through a pad of Celite, and concentrated to give crude product, which was used for the next step without any further purification.

According to the analysis of related databases, 1964-77-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SRI INTERNATIONAL; JONG, Ling; CHANG, Chih-Tsung; PARK, Jaehyeon; (71 pag.)WO2016/114816; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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 39070-14-9, Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

To a suspension of N,N’-bis(2-bromoethyl)phosphorodiamidic acid (50mg, 0.16mmol), 1-methyl-2-nitroimidazole-5-methanol (50mg, 0.32mmol), and PPh3 (84mg, 0.32mmol) in THF (15mL) was added DIAD (0.13mL, 0.32mmol) at 0C. After the addition of DIAD, the reaction mixture was warmed to room temperature and stirred overnight. The solvent was removed, and the residue was purified by column chromatography on silica gel (DCM: MeOH=50:1) to afford compound 14 (37mg, 51%) as yellow gum. 1H NMR (400MHz, DMSO) delta 7.25 (s, 1H), 5.05-4.99 (m, 2H), 4.98 (d, J=7.6Hz, 2H), 3.94 (s, 3H), 3.42 (t, J=6.9Hz, 4H), 3.17-3.05 (m, 4H). 13C NMR (101MHz, DMSO) delta 146.1, 134.1(d, J=8.0Hz), 128.2, 55.7 (d, J=4.3Hz), 42.7, 34.3, 34.1 (d, J=5.0Hz). HRMS (ESI): m/z Calcd for C9H17Br2N5O4P, [M+H]+: 469.9204, found: 469.9186.

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, (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Chen; Zhang, Qiumeng; Lu, Wei; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 135 – 141;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57531-37-0, 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. 57531-37-0, name is 2-Chloro-5-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 1 Preparation of 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole Sodium hydrogencarbonate (1.25 g, 14.91 mmol) 5 was added to a solution of 2-chloro-4-nitro-1H-imidazole (2 g, 13.56 mmol) and epichlorohydrin (1.38 g, 14.91 mmol) in acetonitrile (60 ml), and the resulting mixture was stirred under reflux for 4 hours. The reaction mixture was allowed to return to room 10 temperature, and concentrated under reduced pressure. To the residue, water (20 ml) was added, the resulting mixture was extracted with methylene chloride (15 ml) twice, and the extracts were dried over sodium sulfate, and then filtrated. The filtrate was concentrated 15 under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1/1) to afford 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole (2.04 g, yield 63percent) as a light yellow oil. 20 1H-NMR (CDCl3) deltappm: 3.51 – 3.70 (2H, m), 4.02 – 4.35 (4H, m), 7.92 (1H, s).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5-nitroimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP1555267; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-62-4,Some common heterocyclic compound, 1072-62-4, name is 2-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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: (bromomethyl)-5-fluorophenyl)(2-fluoro-4,5-dimethoxyphenyl)methanone 4 (0.25 g, 0.68 mmol, 1.0 equiv) and 4-hydroxyl piperidine (150 muL, 1.35 mmol, 2.0 equiv) weredissolved in anhydrous dichloromethane (10 mL) and dryK2CO3 (100 mg, 0.72 mmol, 1.1 equiv) was added, and thenthe mixture was stirred at room temperature for 12 h. Thesolvent was removed by rotary evaporation and the residuewas purified by flash column chromatography over silica gelwith the system (14% ethyl acetate/petroleum ether, adding1.4% ammonia water) to obtain compound (5-fluoro-2-((4-hydroxypiperidin-1-yl)methyl)phenyl) 2-fluoro-4,5-dimethoxyphenyl)methanone 5a (0.2 g, 77%) as a yellow solid.The intermediates 5b-5g, 7a-7k, 9a-9g, 11a-11b wereprepared in a similar manner

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Xiu E; Kong, De Peng; Ban, Shu Rong; Ge, Rui; Li, Qing Shan; Medicinal Chemistry Research; vol. 28; 8; (2019); p. 1319 – 1337;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem