Month: June 2021

Synthetic Route of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.

To a suspension of tert-butyl 4-({[2-amino-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (I-55) (1 1 .08 g, 27.2 mmol), 4-bromo-1 -methyl-1 H-imidazole (5.26 g, 32.7 mmol), Cs2C03 (2 N in H20, 27.2 mL, 54.5 mmol) in toluene (50 mL) and EtOH (150 mL) was added Pd(PPh3)4 (4.72 g, 4.08 mmol). The mixture was thoroughly degassed with N2 three times and the brown suspension was then stirred at 85 C for 16 hr under N2. LCMS showed the desired product by mass had formed. The reaction mixture was concentrated under vacuum to give a residue, which was diluted with CH2CI2 (300 mL), washed with water (50 mL), brine (30 mL), dried over Na2S04 and concentrated to give the crude product which was purified twice by silica gel chromatography (0 to 5% MeOH in CH2CI2 followed by CH2CI2/MeOH = 1 /0 to 20/1 ) to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 H-imidazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (~ 5.9 g as a brown solid. ~ 90% purity). This material was diluted with EtOAc / CH2CI2 (5:1 , 60 mL) and heated to 60 C until a clear solution was obtained. Cooling the solution to 25 C with concomitant reduction of the volume under reduced pressure (~10 mL) lead to the appearance of a precipitate. The suspension was filtered, the filter cake was washed with EtOAc/petroleum ether (1 :1 , 10 mL) and dried under vacuum to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 H-imidazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (1-106) (4.38 g, 42%) as a purple solid.

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, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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. Formula: C8H6N2O

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0°C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion using general procedure 3, 1-(2-aminoethyl)-N-[(3-chloropyridin-2-yl)methyl]-1 H- pyrazole-4-carboxamide dihydrochloride (261 ) (200 mg, 0.54 mmol), 1 H-benzimidazole-2-carbaldehyde (94.5 mg, 0.65 mmol) and DIPEA (0.38 ml, 2.16 mmol) in MeOH (8 ml) at room temperature for 16 h, followed by addition of NaBH^ (30.6 mg, 0.81 mmol) gave the title compound (127 mg, 56percent) as a pale green foam after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.17 (s, 1 H), 8.51 – 8.46 (m, 2H), 8.23 (s, 1 H), 7.92 (dd, J = 8.1 , 1.4 Hz, 1 H), 7.90 (s, 1 H), 7.58 – 7.41 (br m, 2H), 7.37 (dd, J = 8.1 , 4.7 Hz, 1 H), 7.17- 7.08 (m, 2H), 4.62 (d, J = 5.6 Hz, 2H), 4.23 (t, J = 6.2 Hz, 2H), 3.92 (br s, 2H), 2.98 (br s, 2H) HPLCMS (Method C): [m/z]: 410.2 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3314-30-5, its application will become more common.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-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 33468-69-8, category: imidazoles-derivatives

Sodium hydride (60 mass %) in 54 mineral oil (41.6 mg, 1.04 mmol) is added to a solution of 61 4-(trifluoromethyl)-1H-imidazole (96.3 mg, 0.694 mmol) in 56 DMF (5.0 mL) at 0 C. The mixture is stirred at room temperature for 30 minutes. 40 [3-[3-[6-(4-Isopropyl-1,2,4-triazol-3-yl)-2-pyridyl]-2-oxo-imidazolidin-1-yl]cyclobutyl] methanesulfonate (162.0 mg, 0.347 mmol) is added at room temperature, the mixture is heated to 90 C., and stirred for 17 hours. The reaction is quenched with water (20 mL) and the product is extracted with DCM (3×40 mL). The organic extracts are dried over Na2SO4 and concentrated in vacuo. The residue is purified by HPLC under the following conditions column: SunFire C18 5 mum, 30*100 mm, eluting with a gradient of 28%-43% of 57 ACN (0.1% FA) in 34 H2O (0.1% FA) over 10 minutes and stop at 17 minutes; flow rate: 30 mL/minutes. t(R) 7.5 minutes. The material is concentrated, dissolved in 21 water, and lyophilized to give the 62 title compound. ES/MS (m/z): 461.0 (M+1), 1H NMR (500 MHz, CDCl3) delta 8.36 (s, 1H), 8.33 (d, J=8.3 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.81 (t, J=8.0 Hz, 1H), 7.65 (s, 1H), 7.43 (s, 1H), 5.58-5.52 (m, 1H), 4.90-4.85 (m, 1H), 4.72-4.69 (m, 1H), 4.09 (t, J=8.0 Hz, 2H), 3.65 (t, J=8.0 Hz, 2H), 3.11-3.05 (m, 2H), 2.76-2.70 (m, 2H), 1.57 (d, J=7.0 Hz, 6H).

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

Reference:
Patent; Eli Lilly and Company; LIU, Lian Zhu; ZHANG, Haizhen; WANG, Xiaoqing; LIU, Gang; (14 pag.)US2019/71413; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

General procedure: A solution (0.05mol-%) of the appropriate furan-2-one (1 eq.) in dry diethyl ether (DEE) was mixed with the N-heterocyclic carbaldehyde (1, 2 or 3 eq.) under a nitrogen atmosphere at 0C. After stirring for 30min, excess dry diethylamine (4 eq.) was added dropwise. Stirring was continued for 30min. The solution was allowed to warm up over night and the product usually precipitated as fluffy powder. The precipitate was washed with cold DEE and dried in vacuo.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uhrner, Fabian; Lederle, Felix; Namyslo, Jan C.; Gjikaj, Mimoza; Schmidt, Andreas; Huebner, Eike G.; Tetrahedron; vol. 73; 30; (2017); p. 4472 – 4480;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H4N2

a. 4-(1H-Imidazol-1-yl)-nitrobenzene To a solution of 4-fluoronitrobenzene (25 g; ~ 0.18 mol) in 250 ml N,N-dimethylformamide was added imidazole (50 g; ~ 0.74 mol). The reaction mixture was stirred at 140C for 2 h, and then poured into ice-water to give the title compound as a precipitate. Yield: 32 g (~ 94%). M.p. 199-202C.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NOVO NORDISK A/S; EP698024; (1997); B1;,
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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., SDS of cas: 39070-14-9

A solution of triphosgene (62 mg, 0.21 mmol) in DCM (4.0 mL) was added to a stirred solution of A13 (prepared as described in: WO 2013/055987; 500 mg, 0.52 mmol) and Et3N (120 mg, 1.18 mmol) in DCM (20 mL) at 22 C. The mixture was stirred at that temperature for 2 h. A solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (112 mg, 0.71 mmol) in DCM (1 mL) was then added, followed by nBu2Sn(OAc)2 (3 drops). The resulting solution was stirred at 22 C for 16 h under N2 then was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM/MeOH = 30/1) to give A14 as a yellow solid (180 mg, 31%). LCMS (condition A): RT = 1.11 min, m/z = 1136.9 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Dragovich, Peter S.; Broccatelli, Fabio; Chen, Jinhua; Fan, Peter; Le, Hoa; Mao, Weiguang; Pillow, Thomas H.; Polson, Andrew G.; Wai, John; Xu, Zijin; Yao, Hui; Zhang, Donglu; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5300 – 5304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-23-3, 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 2034-23-3 as follows.

Example 27; Prcparatiort of 5-((butyIthio)acetyl)-6-chloro-l,3-dimethyl-l,3-dihydro-2f/- benzimidazol-2-one (27); (i) 5-Chl«?>- ,3-dime-liyl-l,3-dihydr-2H-beimaiidazo.-2-onc; 5-Chloro-l ,3-dihydro-2/?-ben^imidazol-2-0Qc (7.040 g, 41.8 mmol) was dissolved in anhydrous DMF (100 ml), anhydrous potassium carbonate (34.707 g, 251 mmol) and iodomcthane (15.5 ml, 249 mmol) were added and the mixture stirred at room temperature overnight. The reaction mixture was poured into chloroform (400 ml) and mixed well then filtered and the filtrate evaporated to dryness. The resultant residue was dissolved in a mixture of ethyl acetate (500 in I) and water (200 ml), the ethyl acetate phase was washed with water (2 x 100 ml) and brine (100 ml), dried over anhydrous magnesium sulfate and filtered, The filtrate was evaporated to dryness to give the title compound (J.163 g, 87% yield) as a brown powder.1H nmr (400 MH?-, CDCIa) delta 3.37-3.42 (m, 6H); 6.87 (d, J – 8.0Hz, IH); 6.97 (d, J = 1.6Hz, IJ I); 7.07 (dd, J = 8.2, 1.8Hz, IH).

According to the analysis of related databases, 2034-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORTICAL PTY LTD; WO2007/70961; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

Add 2-propylimidazole (0.22 g, 2.04 mmol) to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.20 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 further concentration, extraction, column chromatography separation, drying and the like, the intermediate VII-4 (0.45 g) is obtained, the yield is 72.6%;a white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Propylimidazole, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, Recommanded Product: 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole

A mixture of Compound 2 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533 g, 2.1 mmol), bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)C12) (0.060 g,0.08 mmol) and anhydrous potassium acetate (KOAc) (0.3 93g, 4 mmol) in 1 ,4-dioxane (20 ml) was heated at 80 C. under argon overnight. Afier cooling to RT, the whole was diluted with ethyl acetate (80 ml) then filtered. The solution wasabsorbed on silica gel, then purified by column chromatog-raphy (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid3 (0.64 g, in 81% yield).

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-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Khan, Sazzadur Rahman; Zheng, Shijun; Li, Sheng; Mochizuki, Amane; Okada, Keisaku; US2015/87685; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4,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.

To a 1000 ml flask were added 108.3 g (1.59 mol) of imidazole and 630 g of tetrahydrofuran. After the atmosphere of the system was replaced with nitrogen, the imidazole was dissolved under stirring. Thereto was added dropwise 39.3 g (0.2 mol) of diphosgene at room temperature over a period of 2 hours. After completion of the dropwise addition, the stirring was continued at room temperature for 1 hour and then the whole was heated to 55C, followed by continuous stirring for another 1 hour. Imidazole hydrochloride yielded as a by-product was filtrated with heat and was then washed with 100 g of tetrahydrofuran. The imidazole hydrochloride filtrated off was dried under reduced pressure at 40C to obtain 83.2 g (0.796 mol) of imidazole hydrochloride (recovery of 100%). A filtrate containing CDI was concentrated and subjected to toluene-crystallization, and CDI was filtrated off under a nitrogen atmosphere. The CDI filtrated off was dried under reduced pressure at 40C to obtain 58.0 g (0.358 mol) of CDI as white crystals (yield 90%). M.p. 111.2 to 118.6C.

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

Reference:
Patent; Hodogaya Chemical Co., Ltd.; EP1731510; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem