Tag: M.W=100-200

The chemical industry reduces the impact on the environment during synthesis 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, I believe this compound will play a more active role in future production and life. 2849-93-6

At room temperature,3.0 g (18.6 mmol) of 1H-benzimidazole-2-carboxylic acid was placed in a 100 mL eggplant type flask,Add 30mL of thionyl chloride, 79 reflux reaction 4h, after the end of the reaction evaporated solvent.Add 30mL ammonia water, 70 reaction 5h, cooling the reaction solution,Filtration of yellow solid, dry. The yield was 55%.

The chemical industry reduces the impact on the environment during synthesis 2849-93-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 312-73-2

The 2 – trifluoromethyl – 1H – benzimidazole 2 (1.35g, 10mmol) added to the is provided with a 15 ml round bottom flask in acetone, stirring to dissolve into the ene (alkyne) propyl bromide (0.87 ml, 10mmol) and K2CO3(2.07g, 15mmol), heating to reflux, TCL detection, after the reaction is complete, cooling, filtering to remove the solid, dichloromethane is used for washing the solid, acetone solution concentration after mixing with the dichloromethane solution, H for2O washing (15 ml ¡Á 3), organic phase with anhydrous MgSO4Drying, filtering the concentrated to obtain the crude product. To obtain 1 – allyl -2 – trifluoromethyl – 1H – benzimidazole (3) 2.10g, yield 94.34%.aceo

Statistics shows that 312-73-2 is playing an increasingly important role. we look forward to future research findings about 2-(Trifluoromethyl)-1H-benzo[d]imidazole.

Reference:
Patent; Zhejiang University of Technology; Zhu, Bingchun; Wang, Yuguang; Dong, Huichan; (15 pag.)CN104496976; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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¡ãC, 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 to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(3-chloropyridin-2-yl)methyl]-1 ,3- thiazole-4-carboxamide dihydrochloride (193) (320 mg, 0.79 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (127.3 mg, 0.87 mmol), DIPEA (0.32 ml, 2.0 mmol) and MgSQ (300 mg) in MeOH (20 ml) at room temperature for 16 h, followed by addition of NaBh (60 mg, 1.59 mmol) gave the title compound (191 mg, 52percent) as a white solid after purification by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.18 (s, 1 H), 8.72 (t, J = 5.6 Hz, 1 H), 8.49 (dd, J = 4.7, 1.3 Hz, 1 H), 7.95 (dd, J = 8.1 , 1 .3 Hz, 1 H), 7.54 (s, 1 H), 7.46 (s, 1 H), 7.38 (dd, J = 8.1 , 4.7 Hz, 1 H), 7.17- 7.09 (m, 2H), 4.65 (d, J = 5.5 Hz, 2H), 3.98 (d, J = 4.1 Hz, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.95 (q, J = 6.1 , 5.3 Hz, 2H, 2.74 (s, 1 H) HPLCMS (Method C): [m/z]: 461 [M+H]+

The synthetic route of 1H-Benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

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

1003-21-0, The chemical industry reduces the impact on the environment during synthesis 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1.3 M in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C.) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C. in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 10: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C.) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C. with an ice bath and carefully quenched with 2 N aqueous HCl to pH=7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phase split and the organic layer was washed with brine (2*200 mL), dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and the suspension was then filtered to afford the title compound as a solid.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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. 33543-78-1.

First step The compound (85) (2.50 g) was dissolved in pyridine (25 ml), trityl chloride (5.47 g) and dimethylaminopyridine (2.40 g) were added, the mixture was stirred at 100¡ãC for 22 hours. Water was added, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography to afford the compound (86) (2.81 g). 1H-NMR (CDCl3), delta: 0.94 (3H, t, J = 7.1 Hz), 3.82 (2H, q, J = 7.1 Hz), 6.97 (1H, d, J = 1.0 Hz), 7.12 (7H, m), 7.28-7.30 (9H, m).

The synthetic route of Ethyl 1H-imidazole-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; EP2305672; (2011); 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. 2302-25-2 name is 4-Bromo-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. 2302-25-2

1 (300 mg, 2.05 mmol), DCM (10 mL), TEA (3.0 eq), (Boc)20 (1.2 eq), 0C for 10 min; gradually warmed to RT for 10 min and stirred. After 16 h, a non-polar product was observed by TLC. The reaction was quenched with water and extracted with EtOAc (2X20 mL). The combined organic layer was washed with water and dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the crude which was purified by silica gel column chromatography [using 100-200 mesh, eluting with 20% EtOAc-hexane] to afford 320 mg of 2 as white solid. Repeat preparation with 1 (1 g, 6.83 mmol), DCM (20 mL), TEA (3.0 eq), (Boc)20 (1.2 eq), 0 oC-RT. After 16 h, one non-polar product was observed by TLC. The reaction mixture was quenched with water and extracted with EtOAc (2X30 mL). The combined organic layer was washed with water and dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the crude which was purified by silica gel column chromatography [using 100-200 mesh, eluting with 20% EtOAc-hexane] to afford 1.2 g of 2 as white solid.

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

Reference:
Patent; UNITHER VIROLOGY, LLC; RAMSTEDT, Urban; WARFIELD, Kelly Lyn; TRESTON, Anthony; (147 pag.)WO2016/73652; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, Name is 5-Iodo-1H-imidazole, 71759-89-2, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Et3N (0.59 mL, 4.25 mmol) was added to a solution of 4-iodoimidazole [71759-89-2] (750 mg, 3.87 mmol) in DCM (30 mL). The reaction mixture was stirred at room temperature for 5 min and trytil chloride (1.19 g, 4.25 mmol) was added. The reaction mixture was stirred at 40 C for 16 h. The reaction mixture was diluted with NaHCCh (sat., aq.) and extracted with DCM. The organic layer was dried (MgS04), filtered and the solvent were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 60:40) to afford 1-169 (976 mg, 58%).

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 26663-77-4, name is Methyl benzimidazole-5-carboxylate, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 26663-77-4

tert-butyl-2-chloro-4-fluorobenzoate (200 mg, 0.867 mmol), methyl lH-benzimidazole-5- carboxylate (214 mg, 1.214 mmol) and potassium carbonate (359 mg, 2.60 mmol) in dry acetonitrile (12 mL) was stirred at 85C for 6 h. The reaction mixture was cooled to RT and the solid was filtered and washed with EtOAc. The filtrate was concentrated and purified by flash chromatography (ISCO CombiFlash system, 80g Silica gel column, 0-60% EtOAc in hexane as as eluting solvent) to afford the product as a mixture of two regioisomers. Further separation of this mixture of products by SFC technique on chiral AD-H column and using 55% MeOH/C02 as mobile phase yielded compound 18A-a, methyl l-(4-(tert-butoxycarbonyl)-3-chlorophenyl)- lH-benzo[d]imidazole-6-carboxylate, and compound 18A-b, methyl l-(4-(tert-butoxycarbonyl)- 3- chlorophenyl)-lH-benzo[d]imidazole-5-carboxylate. For compound 18A-a: methyl 1 -(4-(tert-butoxycarbonvD-3 -chlorophenvD- 1 H- benzo[dlimidazole-6-carboxylate (M+H) calc. = 387.10; found = 387.15. 1H NMR (500 MHz, CD3OD): delta 8.70 (s, br, 1 H); 8.30 (s, br, 1 H); 8.08 (dd, J = 1.5 Hz, J = 8.5 Hz, 1 H); 8.01 (d, J = 8.5 Hz,l H); 7.89 (d, J = 2.5 Hz,l H); 7.86 (d, J = 8.5 Hz, 1 H); 7.74 (dd, J = 2.0 Hz, J = 8.5 Hz, 1 H); 3.95 (s, 3H); 1.66 (s, 9H) For compound 18A-b: methyl 1 -(4-(tert-butoxycarbonyl)-3 -chlorophenyD- 1 H- benzo[dlimidazole-5-carboxylate (M+H) calc. = 387.10; found = 387.15. 1H NMR (500 MHz, CD3OD): delta 8.56 (s, br, 1 H); 8.47 (s, br, 1 H); 8.12 (dd, J = 1.5 Hz, J = 8.5 Hz, 1 H); 8.10 (d, J = 8.5 Hz,l H); 7.89 (d, J = 2.0 Hz,l H); 7.76 (d, J = 8.5 Hz, 1 H); 7.73 (dd, J = 2.0 Hz, J = 8.5 Hz, 1 H); 3.97 (s, 3H); 1.65 (s, 9H) Additional NMR studies (NOE) confirmed the structure assignments of the two products.

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, 26663-77-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 312-73-2

2-Trifluoromethyl-1H-benzimidazole 2 (1.35 g, 10 mmol)Was added to a round bottom flask equipped with 15 mL of acetone,After stirring, an alkene (alkyne) propyl bromide (0.87 mL, 10 mmol)And K2CO3 (2.07 g, 15 mmol),Heating reflux,TCL detection,After the reaction is complete,Cooling cooling,The solid was removed by filtration,The solid was washed with dichloromethane,The acetone solution was concentrated and mixed with the dichloromethane solution,Washed with H2O (15 mL x 3),The organic phase was dried over anhydrous MgSO4,Filtered and concentrated to get crude,To obtain 2.06 g of 1-propargyl-2-trifluoromethyl-1H-benzimidazole (3)Yield 91.96%.

Statistics shows that 312-73-2 is playing an increasingly important role. we look forward to future research findings about 2-(Trifluoromethyl)-1H-benzo[d]imidazole.

Reference:
Patent; Zhejiang University of Technology; Wang Yuguang; He Rongjun; Dong Huichan; Zhu Bingchun; (14 pag.)CN104496975; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

705-09-9, Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-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 705-09-9.

Step 2: NaH (60%, l . lg, 45.8mmol, 1.5eq) was added protion-wise to a solution of compound Id (3.4g, 20.1mmol, l .leq) in DMF(50mL) at 0C and the mixture was stirred at r.t for 45min. Compound 5a (5.0g, 18.3mmol, leq) was added to the mixture. The mixture was stirred at r.t over weekend. Water was added and the mixture was extracted with ethyl acetate, the organic layer was washed with water for 3 times, dried, concentrated and purified by column chromatography to give 5b (3.4g, yield: 45.8%) as a white solid.’H NMR(CDC13, 300MHZ, ppm): delta 10.23(s, 1H), 7.72(d, 1H), 7.54(d, 1H)ES-MS m/z: 321(M+H+).

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; WO2011/41399; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem