Tag: M.W=100-200

4857-06-1, Adding a certain compound to certain chemical reactions, such as: 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, 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 4857-06-1.

Step3: Under nitrogen protection,2-Chlorobenzimidazole (1.41 g, 9.2 mmol) was added to the reaction vessel.Phenylboronic acid (1.02 g, 8.4 mmol),Tetrakistriphenylphosphine palladium (0.09g, 0.08mmol),Potassium carbonate (3.48g, 25.2mmol),Toluene 60mL, ethanol 20mL and distilled water 20mL,Stir at 120 C for 3 h.After the end of the reaction, the reaction was quenched with distilled water, ethyl acetate was extracted, and the organic layer was dried over MgSO..The solvent was removed by distillation under reduced pressure.After purification by silica gel column chromatography, Intermediate 75-3 (1.22 g, 75%) was obtained.

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (34 pag.)CN108409667; (2018); A;,
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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 1003-21-0

Example 27: N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2- (1-hydroxy-1-methyl-ethyl)-3-methyl-3H-imidazol-4-yl]- [1, 2,3] triazol-1-yl}-4- methyl-benzamide; Ethyl chloroformate (1.19 mL, 12.4 mmol) in MeCN (5 mL) was added dropwise to a 1.00 g (6.21 mmol) of 5-bromo-1-methyl-1H-imidazole (Aldrich) in 30 mL of MeCN under N2. The mixture was stirred and allowed to warm to rt overnight. The mixture was concentrated and the residue was treated with 2M NaOH (100 mL) and extracted with CHUCK (3 x 100 mL). The combined extracts were washed with brine, dried with MgS04, filtered, concentrated, and chromatographed (0-50% EtOAc in hexanes) to give the 5-bromo-1-methyl-lH-imidazole-2-carboxylic acid ethyl ester as a yellow oil (800 mg).

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/90333; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 23785-21-9 name is Ethyl 1H-imidazole-4-carboxylate, 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. 23785-21-9

The starting material for the above process was obtained as follows: A suspension of ethyl imidazole-4-carboxylate (1.4 g), triethylamine (1.2 g) and chloroform (20 ml) was stirred at room temperature while trityl chloride (3.06 g) was added, and the mixture was stirred at room temperature for 1 h. The resulting solution was washed with water, dried and evaporated to dryness under reduced pressure, and the residue was crystallized from a mixture of ethyl acetate and cyclohexane, to give ethyl 1-tritylimidazole-4-carboxylate, mp 163-164.

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

Reference:
Patent; Imperial Chemical Industries plc; US4935437; (1990); 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 1003-21-0 as follows. 1003-21-0

A solution of compound 101a ((1.6 g, 10 mmol), compound sodium 4-(tert-butyl)benzenesulfinate (3.3 g, 15 mmol) and Cul (1.9 g, 10 mmol) in DMF (20 mL) was heated at 110 C for 18 hours under N2. The reaction was then cooled down and filtered. H2O (100 mL) was added to the filtrate and the mixture was extracted with EtOAc (100 mLx 3). The combined organic layers were dried with anhydrous Na2SO4 and concentrated with a Rotavapor. The residue was purified by silica gel chromatography (Petroleum Ether/EtOAc = 10/1 to 2/1) to give the chemical 102a (1.18 g, 42% yield). 1H NMR (CDC13, 400MHz): delta (ppm) 7.83 (d, 2H, J = 8.4 Hz), 7.72 (s, 1H), 7.53 (d, 2H, J = 8.4 Hz), 7.48 (s, 1H), 3.71 (s, 3H), 1.31 (s, 9H). m/z 279 (M+H)+

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ST. JUDE CHILDREN’S RESEARCH HOSPITAL; CHEN, Taosheng; LIN, Wenwei; WANG, Yueming; (239 pag.)WO2017/165139; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic 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 16042-25-4, 16042-25-4

PREPARATION 33 1-amino-N-phenyl-1H-imidazole-2-carboxamide a) N-phenyl-1H-imidazole-2-carboxamide To a solution of 1H-imidazole-2-carboxylic acid (0.975 g, 8.7 mmol) in DMF (30 mL) were added aniline (0.67 mL, 8.7 mmol), EDC¡¤HCl (2.54 g, 13.05 mmol) and HOBt (1.76 g, 13.05 mmol). The reaction mixture was stirred at room temperature for 21 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated. The crude residue was purified by flash chromatography (2% to 3% methanol in dichloromethane) to yield 1.55 g (96% yield) of the title compound. LRMS (m/z): 188 (M+1)+.

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, 2-Imidazolecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Almirall, S.A.; EP2518070; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Add 1-methyl-2-mercaptoimidazole (0.23 g, 2.04 mmol) to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.30 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After concentration, extraction, column chromatography separation, drying and the like, the intermediate VIII (0.34 g) is obtained in a yield of 54.2%;White solid,

The synthetic route of 1-Methyl-1H-imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei¡¤lamohan¡¤laao¡¤yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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 934-22-5 as follows.

Example 133; N-1H-Benzimidazol-5-yl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 2,2,2-Trichloroethyl 1H-benzimidazol-5-ylcarbamate; To a solution of 1H-benzimidazol-5-amine (1.00 g, 7.51 mmol) and pyridine (0.73 ml, 9.01 mmol) in tetrahydrofuran (25 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.25 ml, 9.01 mmol), and the mixture was stirred at room temperature for 1.5 hour . Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 1.49 g (64.4%) of the desired product as a solid was separated by filtration. 1H-NMR (CDCl3) delta; 5.22 (2H, s), 7.27 – 7.29 (1H, m), 7.90 – 8.01 (2H, m), 8.06 (1H, br s), 8.56 (1H, s), 10.16 (1H, br s).

According to the analysis of related databases, 6-Aminobenzimidazole, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O2, 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. 15788-16-6.

Preparation 26 Methyl 5-benzimidazolecarboxylate A mixture of 10 g of 5-benzimidazolecarboxylic acid, 150 ml of methanol and 100 ml of a 4N solution of hydrogen chloride in 1,4-dioxane was agitated ultrasonically for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, after which 300 ml of methanol and 3.5 g of lithium borohydride were added to the residue and the mixture was stirred for 1 hour. The solvent was then removed by evaporation under reduced pressure and the residue was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The solvent was removed by distillation under reduced pressure, to give 5.44 g of the title compound, melting at 136-138 C.

The synthetic route of 1H-Benzo[d]imidazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5886014; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below.

General procedure: The corresponding imidazole (2 mmol) and 2-bromoethanol or 3-bromo-1-propanol or 4-bromo-1-butanol (2.4 mmol) dissolved in acetone (20 ml). Then K2CO3(6 mmol) and KI (2 mmol) were added. The reaction mixture was stirred at 60oCfor 12h. Filtered, the filtrate was concentrated under reduced pressure and dried under vacuum. The1H-NMR and13C-NMR were consistent with the literature.

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; Hu, Yanping; Li, Na; Zhang, Jiayao; Wang, Ying; Chen, Li; Sun, Jianbo; Bioorganic and Medicinal Chemistry Letters; vol. 29; 9; (2019); p. 1138 – 1142;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

e) {(S)-3-[4-(5-Amino-6-methoxy-pyridin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-pyrrolidin-1-yl}-(1-methyl-1H-imidazol-4-yl)-methanone A solution of 1-methyl-1H-imidazole-4-carboxylic acid (CAS registry 41716-18-1) (36.0 mg, 0.26 mmol) and Et3N (0.11 ml, 0.78 mmol) in DMF (1 ml) was treated with HBTU (CAS registry 94790-37) (107 mg, 0.28 mmol). After stirring at rt for 20 min, the reaction mixture was cooled down to 5¡ã C. and a solution of 2-methoxy-5-[6-((S)-pyrrolidin-3-yloxy)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-pyridin-3-ylamine (88 mg, 0.26 mmol) in DMF (3 ml) was added. The reaction mixture was stirred at rt for 1 h, concentrated and the residue was taken up in DCM (10 ml), washed with a sat. aq. NaHCO3 soln. (5 ml), the organic layer was separated by elution through a separating phase cartridge and concentrated. The residue was purified by flash chromatography on silica gel (heptane/EtOAc 100:0 to 0:100), the combined fractions were concentrated, dissolved in tBuOH/H2O and lyophilized to afford the title compound as a colourless solid (21 mg, 37percent yield). UPLC RtM2=0.85 min; ESIMS: 451 [(M+H)+]. 1H NMR (400 MHz, CD3OD): delta 7.64 (s, 1H), 7.62 (s, 1H), 7.65 m, 1H), 6.93 (m, 1H), 6.70 (m, 1H), 6.20-6.34 (m, 1H), 6.15 (m, 1H), 4.81 (m, 1H), 4.19-4.31 (m, 2H), 3.90-4.05 (m, 4H), 3.55-3.83 (m, 8H), 2.04-2.28 (m, 2H).

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem