Category: 2849-93-6

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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., name: 1H-Benzimidazole-2-carboxylic acid

A mixture of 2-(2-tert-butylphenoxy)pyridin-3-amine (1a) (80 mg, 0.33 mmol), 1H-benzo[d]imidazole-2-carboxylic acid (54 mg, 0.33 mmol) and BOP (172 mg, 0.39 mmol) in DMF was stirred at rt for 3 days. LC-MS showed only a small amount of the desired product. The reaction was diluted with EtOAc (15 mL), washed with 1 N HCl solution, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and evaporated to give the crude product. Purification of the crude product by reverse phase preparative HPLC provided Example 71 (12 mg) as a yellow solid. LC-MS m/z 387.2 [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:
Patent; Bristol-Myers Squibb Company; US2007/4677; (2007); A1;,
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 2849-93-6 as follows. COA of Formula: C8H6N2O2

A mixture of compound 70 (0.7 g, 2.1 mmol, 1 eq), 1H-benzimidazole-2-carboxylic acid (358 mg, 2.2 mmol, 1.1 eq), HATU (881mg, 2.3 mmol, 1.1 eq), TEA (426 mg, 4.2 mmol, 586 tL, 2 eq) in 10 mL of DMF was degassed and purged with N2 3 times, and then the mixture was stirred at 15 C for 12 hours under N2 atmosphere. The reaction mixture was partitioned between 20 mL of water and 20 mL of EtOAc. The organic phase was separated, washed three times with 45 mL of water and 15 mL of brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a residuewhich was purified by flash silica gel chromatography (ISCO; 20 g SepaFlash Silica Flash Column, Eluent of 020% ethyl acetate/petroleum ether gradient 60 mL/min) to give 0.37 g of compound 71(745 imol, 35% yield, 95.9% purity) as a white solid.

According to the analysis of related databases, 2849-93-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2849-93-6, 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. 2849-93-6 name is 1H-Benzimidazole-2-carboxylic acid, 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.

[0401] To a 4 mL sample vial equipped with a magnetic stir bar was placed benzyl (7-amino-5-((2S,4S)-1-((R)-2-amino-3-cyclohexylpropanoyl)-4-(5-(2-hydroxypropan- 2-yl)-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamido)-6,7-dioxoheptyl)carbamate (Intermediate L, 20 mg, 0.028 mmol, 1.0 equiv), 1H-benzo[d]imidazole-2-carboxylic acid (10 mg, 0.062 mmol, 2.2 equiv), HATU (12.7 mg, 0.033 mmol, 1.2 equiv) and DMF (400 muL). The solution was treated with EtN(iPr)2 (15 muL, 0.083 mmol, 3 equiv) and the mixture was stirred at room temperature for 18 h overnight. The reaction mixture was filtered through a 13 mm 0.45 muM PFTE syringe filter and the filtrate was collected. Purification of the filtrate by reverse-phase column chromatograph (Waters XSelect CSH Prep C18, 5 mum, 30 × 75 mm) using 60:40 to 35:65 H2O:MeCN + 0.1% HCO2H as a gradient over 10 minutes afforded the title compound. MS (ESI+) 826 (M+1) ^

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzimidazole-2-carboxylic acid, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 2849-93-6, name is 1H-Benzimidazole-2-carboxylic 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 2849-93-6, category: imidazoles-derivatives

A mixture of tert-butyl 3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidine-1-carboxylate (intermediate 55, 450 mg, 1.479 mmol), trifluoroacetic acid (3.29 mL, 44.4 mmol) and dichloromethane (3 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and dried under high vacuum. The crude 3-(azetidin-3-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (250 mg, 0.598 mmol), 1H-benzimidazole-2-carboxylic acid (97 mg, 0.598 mmol), HBTU (227 mg, 0.598 mmol), triethylamine (0.416 mL, 2.99 mmol) and dry dimethylformamide (2 mL) were added to a 50 mL round bottom flask. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with saturated ammonium chloride and dried over magnesium sulfate before concentrating in vacuo to give the crude material as a tan solid. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g, hexane to ethyl acetate gradient) to provide 3-(1-(1H-benzo[d]imidazole-2-carbonyl)azetidin-3-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (16 mg, 0.048 mmol, 8.01% yield) as off-white solid. M+1=335.1 1H NMR (400 MHz, DMSO-d6) delta ppm 4.42 (t, J=9.29 Hz, 1H) 4.66 (dd, J=10.27, 6.16 Hz, 1H) 4.97-5.03 (m, 1H) 5.21-5.36 (m, 2H) 6.92 (dd, J=7.82, 5.28 Hz, 1H) 7.12-7.18 (m, 1H) 7.18-7.25 (m, 2H) 7.44 (d, J=7.82 Hz, 1H) 7.62 (d, J=8.22 Hz, 1H) 7.84 (dd, J=5.28, 1.37 Hz, 1H) 11.13 (br. s., 1H) 13.16 (br. s., 1H)

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.

Electric Literature of 2849-93-6, A common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-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.

A mixture of tert-butyl-piperazine-1-carboxylate (1.75 g), benzimidazole-2-carboxylic acid (1.69 g), HOBt (1.52 g), WSC (1.75 g), and DMF (35 ml) was stirred at room temperature overnight. To the reaction liquid was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with EtOAc. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; Hex_EtOAc=2:1 (V/V)) to obtain tert-butyl-4-(benzimidazol-2-ylcarbonyl)piperazine-1-carboxylate (2.4 g) as a white powder.

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.

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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C8H6N2O2

To a stirred solution of compound 189 (24 g, 148 mmol) in DCM (250 mL) under inert atmosphere, DIPEA (51.58 mL, 296 mmol) and HATU (84.39g, 222 mmol) were added. To this solution, N,O-dimethylhydroxylamine hydrochloride (21.66 g, 222 mmol) was added and stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and extracted using DCM. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 50% EtOAc/ hexanes to afford compound 190 (15 g, 49.40%) as a white solid. TLC: 5% MeOH/ DCM (Rf: 0.5); 1H NMR (400 MHz, DMSO-d6): delta 13.19 (s, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.54 (d, J=7.6 Hz, 1H), 7.34- 7.24 (m, 2H), 3.83 (s, 6H); LCMS Calculated for C10H11N3O2: 205.09; Observed: 206 (M+1)+.

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; ASSEMBLY BIOSCIENCES, INC.; TURNER, William, W., Jr.; LI, Leping; HAYDAR, Simon, Nicolas; BURES, Mark, G.; RAI, Roopa; FRANCIS, Samson; ARNOLD, Lee, Daniel; (0 pag.)WO2018/160878; (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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Starting from the o-phenylenediamine compound (1.0equiv) and glycolic acid (2.0equiv), the reaction was refluxed in the presence of a 4.0 mol/L aqueous hydrochloric acid solution, and the TLC was traced until the reaction of the starting material was complete, and the reaction solution was cooled. To room temperature,Adjusting the pH to 7 with 20% NaOH, standing to precipitate a solid, suction filtration, and drying to obtain compound 5; transferring compound 5 to a round bottom flask,Add NaOH aqueous solution,KMnO4 (2.5 equiv) was added in portions at 80 C with stirring, and the reaction was continued after the addition.After all the raw materials were completely reacted, the reaction solution was cooled to room temperature, and the filtrate was filtered by suction.Adjust the pH to neutral with 20% aqueous HCl solution to precipitate a solid.Drying by suction filtration to obtain compound 6;Compound 6 with DMF(1.0equiv) dissolved, then added 1-hydroxybenzotriazole (HOBt, 1.1equiv)And 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 equiv),The reaction was stirred at room temperature for 30 min, and then compound 4 (1.1 equiv) was added to the reaction solution.Continue to stir the reaction,The TLC traces to the completion of the reaction of the starting material, and the reaction solution is poured into ice water.It was then extracted with ethyl acetate and the organic layer was evaporated.The crude product was purified by column chromatography to give the allyl intermediates Sb.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Jiang Xiaoding; (74 pag.)CN109336887; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1H-benzo[djimidazole-2-carboxylic acid (161 mg, 990 imol, 1.2 eq) in 2 mL of DMF was added HATU (377 mg, 990imol, 1.2 eq) and TEA (167 mg, 1.6 mmol, 229 tL, 2.0 eq). The mixture was stirred at 15 Cfor 0.5 hour, then tert-butyl N-[(1R,3S)-3-(ethylamino)cyclohexylj carbamate, compound 2,(200 mg, 825 imol, 1.0 eq) was added and the resulting reaction mixture was stirred at 15 Cfor additional 15.5 hours. The reaction mixture was partitioned between 5 mL of water and 5 mL of ethyl acetate. The organic phase was separated, washed twice with 10 mL of brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give an oil. The oil was purified by prep-TLC (Si02, eluting with petroleum ether: ethyl acetate = 1:1) to give 150mg of compound 65 (388 imol, 47% yield) as a colorless gum.

The synthetic route of 1H-Benzimidazole-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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. Recommanded Product: 1H-Benzimidazole-2-carboxylic acid

1 H-Benzimidazole-2-carboxylic acid (500 mg, 3.08 mmol) was suspended in EtOH (5 ml_), treated with thionyl chloride (1.12 ml_, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99%) of the crude product. 1H NMR (400 MHz, CD2CI2) delta 1.32 (t, 3H), 4.38 (q, 2H), 7.30 (m, 2H), 7.63 (m, 2H).

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/49681; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2849-93-6,Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Compound 42-a (250.52 mg, 1.55 mmol, 1.03 eq) and HATU (1.14 g, 3.00 mmol, 2.00 eq) were dissolved in dichloromethane (20 mL), and stirred at room temperature for 15 min. Compound 7-a (235.82 mg, 1.50 mmol, 231.19 mL, 1.00 eq) and N,N-diisopropylethylamine (581.58 mg, 4.50 mmol, 785.92 mL, 3.00 eq) were then added, and stirred at room temperature for 18 hours. After the reaction was completed, the reaction solution was added with 150 mL of water, and extracted with dichloromethane (80 mL 3 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?5:2) to give the product of compound 42-b (288.00 mg, yield: 50%) as a yellow oil. LCMS m/z = 302.0 [M+H]+.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; HE, Haiying; WU, Songliang; LUO, Zhi; MOU, Jianfeng; GUO, Fengying; WANG, Chuan; LI, Guoqing; ZENG, Minggao; CHEN, Shuhui; (199 pag.)EP3456711; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem