Month: July 2021

Reference of 41806-40-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 41806-40-0 name is 1-Methylimidazole-5-carboxylic Acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 72 (METHOD T); N-r4-(6,6-Dimethyl-4-oxo-4,5,6,7-tetrahvdrori.31thiazolor5.4-clpyridin-2-yl)-3,4- dihvdro-2H- 1 ,4-benzoxazin-6-yl]- 1 -methyl-lH-imidazole-5-carboxamide; To a stirred solution of Example 42 (0.025 g, 0.08 mmol) in DCM (1 mL) were added l-methylimidazol-5-ylcarboxylic acid (0.013 g, 0.10 mmol), DIPEA (0.02 mL, 0.10 mmol), EDC (0.030 g, 0.16 mmol) and HOBT (0.05 g, 0.04 mmol). The reaction mixture was stirred at r.t. for 18 h, then concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.01 g, 29%) as a yellow oil. 6H (CDCl3) 9.25 (IH, s), 8.46-8.43 (IH, m), 7.33 (IH, dd, J8.9 and 2.4 Hz), 7.07 (IH, d, J 0.9 Hz), 7.02 (IH, d, J0.8 Hz), 6.94 (IH, d, J 8.9 Hz), 5.56 (IH, br. s), 4.36-4.29 (2H, m), 4.16-4.09 (2H, m), 4.11 (3H, s), 2.90 (2H, s), 1.40 (6H, s). LCMS (ES+) 439.4 (M+H)+, RT 2.69 minutes (Method 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylimidazole-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; WO2008/1076; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. Application In Synthesis of 1H-Imidazole

(a) A solution of alpha-bromo-4-toluonitrile (86.6 g) in dichloromethane (1000 mL) is mixed with imidazole (68.0 g). The mixture is stirred at ambient temperature for 15 hours and then diluted with water (1000 mL). Any undissolved solid is removed by filtration and the separated organic solution is then repeatedly washed with water (5*200 mL) to remove excess imidazole, and then dried (MgSO4). The crude product obtained upon evaporation of the solvent can be purified by trituration with cold diethyl ether (200 mL) to obtain 4-(1-imidazolylmethyl)-benzonitrile, m.p. 99-101; HCl salt, m.p. 142-144.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4749713; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 96797-15-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 96797-15-8 name is 4-Iodo-1-trityl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-IODO-L-TRITYL-LH- imidazole (15.0 g, 34 mmoles) in THF (150 ml) at room temperature was added ethylmagnesium bromide (41 ml, 40.7 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (5.6 g, 40.7 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (RIPHENYLPHOSPHINE) palladium (4.0 g, 3.43 mmoles) and 5-bromo-2-methylpyridine (7.0 g, 40.7 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane and washed with an EDTA buffer (at APPROIMATE pH 9) (2x 300 ML), NACI (sat. ) (300 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was dissolved in ethanol (250 ml) and concentrated HCl (13.6 ml) was added to the solution at room temperature. The reaction mixture was heated in a 50C oil bath for 2 hours. Upon cooling, the reaction was filtered and washed with ethyl ether (25 ml) to yield 5- (1H- imidazol-4-yl) -2-methyl-pyridine (5.815g, 63%). MH+ (160).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-1-trityl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; CHIRON CORPORATION; WO2004/96823; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(0044) The original patent for structure 1, FIG. 1 was granted in 1984 to J. Boileau. His synthetic methodology for successfully achieving 1 was the direct nitration of glycoluril using a mixture of N2O5 and 100% HNO3. The yields on his process are claimed to be greater than 85%. It has since been discovered it is possible to successfully synthesize structure 1 using a mixture of acetic anhydride and 100% HNO3 in similar yields without necessitating the making N2O5 directly. Both of these methods yield structure 1 that is highly sensitive to impact and friction (approximately twice more sensitive on both accounts than standard military explosives RDX and HMX) making handling of the material from these processes inherently more dangerous.

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, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; U.S. Army Research Laboratory ATTN: RDRL-LOC-I; Sherrill, William Matthew; Banning, Joseph Erik; (7 pag.)US2016/90388; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 930-62-1,Some common heterocyclic compound, 930-62-1, name is 2,4-Dimethylimidazole, 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.

Compound TX63822: Compound 11 (0.2 mmol) and 2,4-Dimethyl-lH- imidazole (19.2 mg, 0.2 mmol) were taken up in toluene (1 mL), and the mixture was stirred at room temperature for 65 h, no reaction happened. Additional 2,4-Dimethyl- lH-imidazole (76.8 mg, 0.8 mmol) and toluene (2 mL) was added, and the mixture was stirred at room temperature for 3h. The reaction mixture was quenched with H20 (10 mL) and extracted with CH2C12 (2×5 mL). The combined organic phase was filtered through a Na2S04 plug, then directly loaded on a silica gel column and purified by column chromatography (silica gel, twice, 0-65 % EtOAc in Hexanes then 0-60% EtOAc in Hexanes) to give the compound TX63822 as a white solid (22.2 mg, 22%). 1H NMR (500 MHz, CDC13) delta 8.02 (s, 1H), 7.22 (s, 1H), 6.03 (s, 1H), 3.25- 3.30 (m, 1H), 3.06 (d, 1H, J = 4.5 Hz), 2.56 (s, 3H), 2.42-2.51 (m, 1H), 2.19 (s, 3H), 1.95-2.16 (m, 3H), 1.83-1.93 (m, 2H), 1.58-1.77 (m, 4H), 1.15-1.45 (m, 6H), 1.44 (s, 3H), 1.30 (s, 3H), 1.24 (d, 3H, J = 6.5 Hz), 1.06 (s, 3H), 1.04 (s, 3H), 0.95 (s, 3H); m/z 556 (M+l).

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; ANDERSON, Eric; JIANG, Xin; VISNICK, Melean; BENDER, Christoper, F.; LIU, Xiaofeng; WO2012/125488; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-32-7, name is 1H-Benzo[d]imidazol-2-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 934-32-7, Product Details of 934-32-7

General procedure: A mixture of -Fe2O3starch-n-butyl SO3H (10 mg),aromatic aldehyde (1.0 mmol), dimedone (1.0 mmol),2-aminobenzimidazole (1.0 mmol) was heated in an oilbath (100 C) for the appropriate reaction time until thecompletion. The progress of the reaction was monitoredby TLC (n-hexane:ethyl acetate, 8:4). After completion ofthe reaction water (10 mL) was added and the catalyst wassegregated using an external magnet, washed with chloroform,dried out, and used directly without an appreciableloss of its activity for the next run. The product was purifiedby recrystallization from EtOH and dried in air.

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:
Article; Shamsi-Sani, Mahnaz; Shirini, Farhad; Mohammadi-Zeydi, Masoud; Journal of Nanoscience and Nanotechnology; vol. 19; 8; (2019); p. 4503 – 4511;,
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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7BrN2

[0003901 To a stirred solution of compound 1 (0.2 g, 1 eq) in aq. ammonia solution (2 mL), copper chloride (catalytic amount) was added and heated at 100 °C for 5 h in a sealed tube. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20percent methanol in dichloromethane and filtered. The filtrate was concentrated under reduced pressure to afford title compound 2. LCMS (mlz): 148.00 (M + 1).

The synthetic route of 53484-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1219741-19-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1219741-19-1 name is 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of potassium phosphate, tribasic (2 M solution in water; 21 mL, 42 mmol), Pd(PPh3)4 (0.324 g, 0.280 mmol), 4-biphenylboronic acid (3.94 g, 1 .9 mmol) and 6-chloro-5-iodo-2- (methylsulfonyl)-lH-benzimidazole (Intermediate 1, 5 g, 14 mmol) in dioxane (70 mL) was heated at 100C for 5 h. The aqueous phase was removed and the organic phase wasconcentrated, diluted with EtOAc and DCM, and filtered. The filtrate was concentrated to afford the desired product as a white solid, which was used in the next step without further purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; JIANG, Jinlong; KASSICK, Andrew, J.; KEKEC, Ahmet; SEBHAT, Iyassu, K.; WO2011/106273; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 18075-64-4, name is 1-Phenyl-1H-imidazole-4-carboxylic acid, 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. Recommanded Product: 18075-64-4

DMSO (0.5 mL) was added to a mixture of 1-phenyl-1H-imidazole-4-carboxylic acid (34 mg, 0.18 mmol) and 1-pyrrolo[1,2-c]pyrazin-1-yl-pyrrolidin-3-ylamine dihydrochloride salt (50 mg, 0.18 mmol). To this was added triethylamine (0.100 mL, 0.72 mmol) followed by HATU (76 mg, 0.20 mmol). The mixture was allowed to stir for 30 min after which time it was diluted with dichloromethane (1.0 mL), washed with water (3*1.0 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC (10:90-95:5 MeCN:H2O+0.1% TFA). The combined product fractions were lyophilized to give the TFA salt of the product as a pale yellow solid (49 mg, 0.10 mmol, 56% yield).

The synthetic route of 1-Phenyl-1H-imidazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a three-necked flask equipped with a stirrer and a thermometer, 1.44 g (8.0 mmol) of N-octylimidazole, 0.56 g (4.4 mmol) 1,3-dichloro-2-propanol, stirring at 115 ° C ~ 125 ° C reaction, TLC follow the progress of the reaction, about 8 ~ 12h after the end of the reaction. The crude product was recrystallized from a mixed solvent of chloroform and ethyl acetate, A white powdery solid was obtained 1,1 ‘-dioctyl-3,3′(2-hydroxy-1,3-propylene) imidazole hydrochloride (1.02 g, yield 52.1percent).

The synthetic route of 1-Octyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qiqihar university; Wang, LiYan; Deng, QiGang; Zheng, YongJie; Huo, shichao; Liu, Jia; Sun, zhu; (10 pag.)CN103951702; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem