Tag: M.W=200-300

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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), A new synthetic method of this compound is introduced below., Formula: C6H12N6O4S

A solution of 158 mg of 2-aminoimidazole sulfate in 0.4 mL of concentrated HCl and 0.4 mL of water is cooled to 0 C. To this solution is added dropwise a solution of 82.8 mg of NaNO2 in 0.6 mL of water. The resulting yellow solution is stirred at 0 C. for 30 minutes and is added slowly to a suspension of 244 mg of 2,2,2-trifluoro-1-(4-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethan-1-one and 504 mg of NaHCO3 in 3 mL of MeOH. The reaction mixture turns red. After the addition is complete, the mixture is filtered and the orange solid collected is dried to yield the crude product, (E)-1-(7-((1H-imidazol-2-yl)diazenyl)-4-methyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethan-1-one. This material is used in the next step without further purification

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H12N6O4S

[2-(2-Amino-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (Cpd 5b). To a flask containing 2-anninoinnidazole sulfate 5a (1 g, 3.8 mmol) in DMF (20 ml_) was added sodium hydride (0.65 g, 16.3 mmol) in small portions with stirring. The temperature was maintained below 30 0C during the addition by means of an ice bath. After stirring for 30 minutes at 25-30 0C, the solution was cooled to 0 0C and (2-bromo-ethyl)-carbamic acid tert-butyl ester (1.7 g, 7.6 mmol) in DMF (1 ml_) was added. After stirring for 1 min the cooling bath was removed and the solution was stirred toward rt for 16 h. The reaction was carefully quenched with water (10 ml_), extracted with EtOAc (4 x 10 ml_), dried over sodium sulfate, filtered, and concentrated to a residue. The residue was stored at < 0.5 mm Hg for 24 h to remove residual DMF, then purified by normal phase chromatography to give compound 5b (0.29 g) as a brown glass. HRMS calcd. for Ci0Hi9N4O2 m/z 227.1508 (M+H), found: 227.1518. According to the analysis of related databases, 1450-93-7, the application of this compound in the production field has become more and more popular. Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2009/58653; (2009); 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. 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

Methyl 2-bromo-1-methyl-1 H-imidazole-5-carboxylate (659 mg) (3-cyanophenyl) boronic acid (600 mg),(1,1′-diphenylphosphinoferrocene) dichloropalladium (200 mg),2 M aqueous potassium carbonate solution (3 ml),A mixture of toluene (10 ml) and ethanol (3 ml) was stirred at 80 C. overnight.The mixture was cooled to room temperature and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (239 mg)

The synthetic route of 120781-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; MIZOJIRI, RYO; CARY, DOUGLAS ROBERT; HIRAYAMA, TAKAHARU; ITO, MASAHIRO; TANAKA, TOSHIO; IMAEDA, YASUHIRO; SASAKI, SHIGEKAZU; TAKAMI, KAZUAKI; FUKUDA, KOICHIRO; KAMAURA, MASAHIRO; MORISHITA, NAO; (133 pag.)JP2017/222626; (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 2963-77-1 as follows. Recommanded Product: 4-(1H-Benzo[d]imidazol-2-yl)aniline

2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid (4-formyl-phenyl)-amide (0.1 mmol, 0.0284 g), 4-(1H-benzoimidazol-2-yl)-phenylamine (0.1 mmol, 0.021 g) and NaBH(OAc)3 (1.0 mmol, 0.211 g) were stirred in DMF (2 ml) at room temperature for 24 h. Then NaBH(OAc)3 (0.5 mmol, 0.11 g) was added to the reaction. The resulting mixture was stirred at room temperature for 36 h. Water (10 ml) was added to quench the reaction. Aq. K2CO3 solution (5 %) was added to neutralize the pH to ca. 7. The formed solid was filtered and washed with water (2 x 4 ml). The title compound was obtained as brown solid (0.042 g, 88 %). 1H NMR delta 4.33-4.30 (m, 6H), 6.72-6.69 (m, 3H), 6.97 (d, J= 8.1 Hz, 1H), 7.12-7.08 (m, 2H), 7.35 (d, J= 8.1 Hz, 2H), 7.55-7.40 (m, 4H), 7.71 (d, J= 8. 1 Hz, 2H), 7.87 (d, J= 8.1 Hz, 2H), 10.02 (s, 1H), 12.41 (br s, 1H). MS m/z = 477 (M+1)

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMCLONE SYSTEMS INCORPORATED; WO2005/42496; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid (12 mg, 0.0436 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (22.6 mg, 0.059 mmol), and TEA (7.2 mg, 0.078 mmol) were dissolved in DMF (0.2 ml), the solution was stirred at 45 C. for 30 minutes, the compound F (10.2 mg, 0.039 mmol) was then added, and the solution was stirred at 45 C. for 12 hours. After the reaction was completed, ethyl acetate was added and the reaction mixture was washed with a saturated aqueous NaCl solution. The organic layer was dried with sodium sulfate anhydrous and filtered, and then the solvent was removed under reduced pressure. The residue was crystallized to obtain a target compound 3-(4-methyl-1H-imidazol-1-yl)-N-(3-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)-5-(trifluoromethyl)benzamide (15.6 mg, 78%). 1H NMR (400 MHz, DMSO-d6) delta 10.71 (1H, s), 10.53 (1H, s), 8.49 (1H, s), 8.43-8.42 (2H, m), 8.26 (1H, s), 8.22 (1H, s), 8.06 (1H, dd, J=8.2, 1.4 Hz), 7.79 (1H, d, J=8.0 Hz), 7.73 (1H, s), 7.58-7.54 (2H, m), 7.04 (1H, d, J=4.0 Hz), 3.61 (2H, s), 2.20 (3H, s). (Exact mass 509.11, m/z 510.1186)

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; Industry-University Cooperation Foundation Hanyang University ERICA Campus; HAH, Jung-Mi; LEE, Jung Hun; KIM, Minjung; (30 pag.)US2018/37589; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 67085-11-4,Some common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, molecular formula is C13H15ClN2O, 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.

Take 5kg of 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1-hydro-imidazole,Fully dissolved in 35 kg of methylene chloride and added at a rate of 1.5 ml/s at 20C5kg of thionyl chloride was slowly warmed to 32C and the reaction was incubated for 1 hour.Then reflux at 60 C for 1 hour, slowly cooled to 15 C to obtain the reaction solution;In the reaction solution, 10 C. water was added at a rate of 0.5 ml/s with stirring, the volume ratio of the reaction solution to water was 0.005:1, and anhydrous sodium carbonate was added at 1.0-1.5 kg/L. Suction filtrationSolid, the liquid was concentrated at 55 C until the dichloromethane evaporated, and dried.This yields 1-(2-chloro-4-(4-chlorophenyl)butyl)-1H-imidazole with a purity of 99.17%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, its application will become more common.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Li Sanxin; Peng Kaifeng; Ling Yonggen; Wen Fengqiu; Gong Yun; Li Fujun; (13 pag.)CN105198818; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. category: imidazoles-derivatives

A mixture of 44 (2.3 g, 9.5 mmol) and NaOH (759 mg, 19 mmol) in MeOH/H20 (20/5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated. The residue dissolved in water, acidified to pH 3 with aqueous HCI and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2504 and evaporated under reduced pressure to give 45 (1.9 g, 88%) as a whitesolid. To a solution of this material (48 mg, 0.21 mmol) in NMP (1 mL) was added SOd2 (38 mg, 0.32 mmol). The reaction was heated at 60 C for 1 hour before 3 (50 mg, 0.21 mmol) and Et3N (85 mg, 0.84 mmol) was added. The resulting mixture was stirred at 60 C for 3 hours. The reaction was directly purified by reverse prep-HPLC and then silica gel prep-TLC to give 4-methyl-N-(3-(4-methyl-1 H-imidazol-1 -yl)-5-(trifluoromethyl)phenyl)-3-phenoxybenzamide (27 mg, 29%) as a slightly yellow solid.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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 28890-99-5, Formula: C13H9N3

Example 4 a) 7.78 g (25 mmol) 1-bromo-3-iodo-benzene, 16.3 g (50.0 mmol) caesium carbonate, 1.24 g (6.50 mmol) copper(I) iodide and 1.50 g (13.0 mmol) L-proline are added to 5.18 g (25.0 mmol) mmol) 5H-benzimidazo[1,2-a]benzimidazole in 100 ml dimethylsulfoxide (DMSO) under nitrogen. The reaction mixture is stirred for 18 h at 100 C. The reaction mixture is poured into water. The organic phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate. The solvent is distilled of. Column chromatography on silica gel with toluene gives the product. Yield 8.35 g (92%).1H NMR (400 MHz, CDCl3): delta 8.25 (s, 1H), 7.90-8.05 (m, 3H), 7.95-8.05 (m, 3H), 7.71 (d, J=7.9 Hz, 1H), 7.65 (d, J=7.9 Hz, 1H). 7.50-7.65 (m, 2H), 7.26-7.45 (m, 4H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; US2012/241681; (2012); 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 144689-93-0

Ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate (100 gm) was dissolved in acetone (2500 ml) and then added potassium carbonate (100 gm), 5-[4′-(bromomethyl)[1,1′-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole (250 gm) and tert-butyl ammonium bromide (15 gm) under stirring at room temperature. The temperature of the reaction mass was raised to 50 to 55 C. and maintained for 15 hours at 50 to 55 C. The reaction mass was cooled to 45 C. and passed over celite bed. The collected filtrate was cooled to 0 to 5 C. and then added a solution of potassium carbonate (36 gm) in water (36 ml) for 1 hour. The temperature of the reaction mass was raised to room temperature and maintained for 16 hours at room temperature. The acetone was distilled off completely under vacuum at below 40 C. to obtain residue. To the residue was added sodium chloride solution (10%, 900 ml) and then added ethyl acetate (1500 ml). The layers were separated and the aqueous layer was extracted. Combined the both organic layers and dried over sodium sulfate. The solvent was distilled off completely to obtain a residual mass. A mixture of acetone (1200 ml), potassium carbonate (100 gm), (4-bromoethyl)-5-methyl-oxo-1,3-dioxane (105 gm) and potassium iodide (17 gm) were added under stirring at room temperature and then the contents were heated to 50 to 55 C. The solution was added to the above residual mass for 1 hour 30 minutes and maintained for 1 hour 30 minutes at 50 to 55 C. The reaction mass was cooled to 45 C. and filtered. The solvent was distilled off completely to obtain residue. Toluene (1500 ml) was added to the residue and the layers were separated. The toluene layer was dried over sodium sulfate and distilled off the layer under vacuum up to obtain clear residual mass. To the residual mass was added methanol (1500 ml) and stirred for 30 minutes at room temperature. The reaction mass was cooled to 10 to 15 C. and maintained for 1 hour 30 minutes. The separated solid was filtered and dried at 40 to 45 C. for 7 hours to obtain 270 gm of trityl olmesartan medoxomil. Trityl olmesartan medoxomil: 98.5%; Trityl olmesartan ethyl ester impurity: 0.35%; Bromo trityl olmesartan medoxomil impurity: 0.35%; Methyl trityl olmesartan medoxomil impurity: 0.34%.

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HETERO RESEARCH FOUNDATION; Parthasaradhi Reddy, Bandi; Rathnakar Reddy, Kura; Muralidhara Reddy, Dasari; Raji Reddy, Rapolu; Ramakrishna Reddy, Matta; Vamsi Krishna, Bandi; US2013/190506; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 120781-02-4, These common heterocyclic compound, 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-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.

(1) 2-bromo-3-methyl -3H- to imidazole-4-carboxylic acid methyl ester (800mg) 4-(trifluoromethyl)benzeneboronic acid(1.04g), tetrakis(triphenylphosphine)palladium(422mg) And as a solvent was stirred in tetrahydrofuran (9), saturated sodium carbonate (3), was added water (1.5), and microwave irradiation for 30 minutes at 120 . After the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (n- hexane: ethyl acetate) [(trifluoromethyl) 4-phenyl] After purification, 3-methyl-2–3H- imidazole-4-carboxylic acid methyl ester ( It was obtained 980mg) as a yellow solid.

Statistics shows that Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 120781-02-4.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem