Category: imidazoles-derivatives

Application of 582-60-5,Some common heterocyclic compound, 582-60-5, name is 5,6-Dimethyl-1H-benzo[d]imidazole, molecular formula is C9H10N2, 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. Benzimidazole-5,6-dicarboxylic acid The compound was prepared from 5,6-dimethylbenzimidazole as described in J.Org.Chem. 1987, 52, 2934.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dimethyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; James Black Foundation Limited; US5795907; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 279226-70-9, name is 1-Methyl-1H-benzimidazole-5-carboxaldehyde, 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. COA of Formula: C9H8N2O

To a solution of 1-methyl-1H-benzoimidazole-5-carbaldehyde (prepared as described in WO0037473) (420 mg, 2.62 mmol) in trimethylsilyl cyanide (2 mL, 15.0 mmol) was added a catalytic amount of zinc iodide. The reaction mixture was stirred at ambient temperature overnight, concentrated under vacuum and the resulting residue dissolved in a 7N solution of ammonia in methanol (10 mL, 70 mmol) in a sealed tube. The mixture was heated for 1.5 hours at 55 C. then cooled to ambient temperature and concentrated under vacuum. The residue was dissolved in 6N aqueous hydrochloric acid (?10 mL) in a sealed tube. The mixture was stirred at 110 C. for 6 hours then cooled and concentrated under vacuum to afford a solid residue. This solid was dissolved in N,N-dimethylformamide (?20 mL). Triethylamine (4 mL, 28.7 mmol) and di-tert-butyl dicarbonate (850 mg,3.93 mmol) were added and the mixture was stirred for 4 hours at ambient temperature. The solvent was then removed, the residue was washed with ether, dried and then dissolved in tetrahydrofuran (55 mL). To this solution was added (S)-2-(2-amino-3-phenylpropinylamino-thiazole-4-carboxylic acid methyl ester (prepared as described in example 3) (800 mg, 2.62 mmol) and the reaction mixture cooled to 0 C. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (500 mg, 2.61 mmol) was added and the reaction mixture was allowed to slowly warm to ambient temperature and then stirred for 48 hours. The reaction mixture was then partitioned between ethyl acetate and water, the ethyl acetate layer was dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography over silica gel gradient eluted between 0 and 50% v/v ethyl acetate in dichloromethane and then gradient eluted between 0 to 4% methanol in dichloromethane. Precipitation of the isolated product from a tetrahydrofuran solution with an excess of hexanes afforded 2-{(S)-2-[2-tert-butoxycarbonylamino-2-(1-methyl-1 H-benzoimidazol-5-yl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as an amorphous white solid (510 mg, 33%). HRMS: Obs. Mass, 593.2167. Calcd. Mass, 593.2177 (M+H)

The synthetic route of 1-Methyl-1H-benzimidazole-5-carboxaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goodnow,, Robert Alan; Huby, Nicholas J.S.; Kong, Norman; McDermott, Lee Apostle; Moliterni, John Anthony; Zhang, Zhuming; US2006/63814; (2006); 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. 60713-78-2, name is 5-Chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H4ClN3O3

Step 2: 5-Chloro-l,3-dimethyl-6-nitro-lH-benzo[JJimidazol-2(3H)-one 5-Chloro-6-nitro-lH-benzo[ ]imidazol-2(3H)-one (1.00 g, 4.7 mmol) was stirred in DMF (50 niL) then potassium carbonate (1.29 g, 9.4 mmol) and iodomethane (2.66 g, 18.7 mmol) were added. The reaction was stirred at 75 C for 1.5 h. The reaction was allowed to cool and solvents were removed under reduced pressure. The residue was partitioned between water and ethyl acetate and the phases were separated. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were through a phase separation cartridge and evaporated to afford a brown solid (1.07 g, 95%), which was taken through to the next step with no further purification.

According to the analysis of related databases, 60713-78-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79505; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1207457-15-5, 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. 1207457-15-5, name is tert-Butyl 2-bromo-1H-imidazole-1-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1. To a mixture of 1 (PCT Int. Appl. (2008), WO 2008079277 A, 4 g, 14 mmol) tert-butyl 2-bromo-lH-imidazole-l-carboxylate (FCH Group, 1.8 g, 7 mmol) and NaOH (3 mL,1.5 M) in toluene (20 mL) and ethanol (2 mL) was added Pd(PPh3)4 (0.084 g, 0.14 mmol) under N2. The resulting mixture was stirred at 120 C for 24 h. The mixture was cooled to RT, treated with water and extracted with EA. The combined organic extracts were washed with water, brine, dried over anhydrous Na2SC>4, filtered and concentrated to give a crude oil. The crude product was purified by recrystallization to afford 2 (1.1 g, 38 %).

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, tert-Butyl 2-bromo-1H-imidazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; CHIANG, Lillian W.; MURPHY, Eain Anthony; KAYSER, Frank; SUN, Qun; FINK, Sarah Jocelyn; (128 pag.)WO2019/79519; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazol-4-amine hydrochloride, its application will become more common.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); 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. 2080-75-3, name is 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 2080-75-3

Obtained through a method the N- acetyl benzylamine piperazine (II) intermediate (19. 6mmol), an alcoholic solution of formaldehyde (16. 3mmol), 5_ methoxy-1,3-dihydro-benzimidazol-2 – one (16. 3mmol) into 30ml of absolute ethanol, at room temperature for 15h. The reaction was concentrated under reduced pressure to give a crude oil. The crude product was purified by silica gel column chromatography to obtain the free base of N- benzyl-2- {4 – [(5-methoxy-2-oxo-2,3-dihydro-benzo -111- [(1] imidazole – 1- yl) methyl] piperazin-1-yl} -acetamide (V-18), 4. 44g, 66.6% yield.

The synthetic route of 2080-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceutical Industry Research Academy; China State Institute of Pharmaceutical Industry; Li, Jiangqi; Weng, Zhije; Cui, Ning; Jie, Peng; Ma, Xiao; (25 pag.)CN105418506; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 84243-58-3, A common heterocyclic compound, 84243-58-3, name is 6-(4-(1H-Imidazol-1-yl)phenyl)-4,5-dihydropyridazin-3(2H)-one, molecular formula is C13H12N4O, 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 4 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinone Bromine (1.6 ml) is added dropwise to a solution of 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinone (3.5 g) in acetic acid (25 ml) at 80 C. The mixture is heated for 5 to 6 hours to complete the reaction. The solid is filtered, washed with ether and converted to the free base which is crystallized from ethanol to yield 1.1 g of the product 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinone: mp. 244-245 C. Anal. calcd for C13 H10 N4 O.1/5H2 O; C, 64.56; H, 4.30; N, 23.17; H2 O, 1.49. Found; C, 64.30; H, 4.36; N, 23.04; H2 O, 1.11.

The synthetic route of 84243-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4353905; (1982); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5098-11-3, name is 5-Amino-1H-imidazole-4-carbonitrile, 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 5098-11-3, Safety of 5-Amino-1H-imidazole-4-carbonitrile

4-amino-5-imidazolecarboxamide hydrochloride was heated to reflux in phosphorus oxychloride for 3.5 hs and after purification gave 4-amino-5-nitrile imidazole. This was resuspended in ethanol saturated with HCl overnight and purification gave 4-amino-5-ethylimino ester imidazole hydrochloride. This was combined with diphenylborinic acid ethanolamine ester in tetrahydrofuran (THF) overnight to yield the title compound.

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, 5-Amino-1H-imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Benkovic, Stephen J.; Shapiro, Lucy; Wright, Rachel; Stephens, Craig; Kahng, Lyn Sue; Berdis, Anthony; Lee, Irene; US2005/227933; (2005); 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. 39811-07-9, name is (5-Fluoro-1H-benzo[d]imidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 39811-07-9

5-Fluoro-1H-benzimidazole-2-carboxylic acid 45 was synthesised using 5-fluoro-1H-benzimidazole-2-yl)methanol 29 (0.10 g, 0.60 mmol) dissolved in acetone (20 mL) and potassium permanganate (0.10 g, 0.63 mmol) dissolved in water (10 mL). 5-Fluoro-1H-benzimidazole-2-carboxylic acid 45 was recovered as bright white crystals in Yield 38%. mp 166-168 C.

According to the analysis of related databases, 39811-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
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. 6953-65-7, name is (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

General procedure: Solution ofbenzimidazole (0.1 mmol) in TfOH (1 mL) and arene (0.1 mL) was magnetically stirred at 140 Cin glass high pressure tube for 2.5 h, then poured into water (50 mL). After extraction with CH2Cl2(3 × 30 mL), the combined extracts were consequently washed with water (50 mL), saturatedaqueous solution of Na2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporatedin vacuo to give crude products, which were subjected to chromatographic separation on silica gelusing petroleum ether/diethyl ether as an eluent.

According to the analysis of related databases, 6953-65-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem