Category: 23814-14-4

Reference of 23814-14-4, 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. 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 9; 2-Oxo-N-(2-oxo-2,3-dihydro-1 H-benzo [d] imidazol-5-yl)-2,3-dihydro-1 H- benzo[d]imidazole-5-carboxide (referred to as DC-0051-Bl); The amide was synthesized by reacting 2-oxo-2, 3-dihydro-lH- benzoimidazolyl-5-carboxylic acid with 5-amino-2, 3-dihydro-lH-benzoimidazol-5- one in the presence of 1,3- N, N-diisopropylcarbodiimide and 1- hydroxybenzotriazole. 1,3- N, N-Diisopropylcarbodiimde (0.504 g; 4 mmol) was added to a solution of 2-oxo-2,3-dihydro-lH-benzoimidazole-5-carboxylic acid (0.448 g; 2.5 mmol), 5- amino-2-oxo-2,3-dihydro-lH-benzoimidazole and 1-hydroxybenzotriazole (0.34 g; 2.5 mmol) in anhydrous N, N-dimethylformamide (10 ml). The reaction mixture was stirred at 40 C for 12 hours. The precipitated product was isolated by filtration of the reaction mixture followed by washing three more times with N, N-dimethylformamide (3 ml). The product was dissolved in dimethylsulfoxide (5ml) and precipitated by diluting the solution with acetonitrile (60 ml). Filtration and drying under vacuum gave 2-Oxo-N-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2,3-dihydro-1H- benzo [d]imidazole-5-carboxide (also referred to as DC-0051-B1) (0.22 g; 28%). ¹H NMR ((CD3)2SO 10.62 (1H, s, NH), 10.53 (1H, s, NH), 9.98 (lH, s, NH) 7.65 (1H, d, J 8Hz) 7.55 (2H, bs) 7.23 (1H, d, J 8Hz) 7.05 (1H, d, J 8Hz) 7.85 (1H, d, J 8Hz).

The synthetic route of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-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 23814-14-4, Quality Control of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

C) 2-Oxo-2, 3-dihydro-lH-benzoimidazolyl-5-carboxyl (I-N-3, 4- dibenzyloxy phenyl) amide; 1, 3- N, N-Diisopropylcarbodiimde (0.412 g; 3.27 mmol) was added to a solution of 2-oxo-2, 3-dihydro-1H-benzoimidazole-5-carboxylic acid (0.584 g; 3.27 mmol) 3,4-dibenzyloxy aniline (1.0 g, 3.27 mmol) and 1-hydroxybenzotriazole (0.442 g, 3.27 mmol) in anhydrous N, N – dimethylformamide (15 ml). After stirring for 16 hrs at room temperature the reaction mixture was poured in water (150 ml). The pH of the mixture was adjusted to 2 with IN hydrochloric acid and stirred for 30 minutes. Filtration and washing the product with ethyl acetate (3 x 10 ml) provided 1.12 grams of 2-Oxo-2, 3-dihydro-l H-benzoimidazolyl-5-carboxyl (1-N-3, 4-dibenzyloxy phenyl) amide. Yield = 73.6 %. ¹H NMR (CD3)2SO 10.5 (1H, s, NH) 7.65 (1H, d, J 8Hz) 7.6 (1H, s) 7.2-7.6 (m, 12H) 7.0 (2H, d, J 8Hz) 5.15 (4H, s).

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:
Patent; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 23814-14-4,Some common heterocyclic compound, 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O3, 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.

Example 14 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (100 mg, 0.245 mmol), 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid (48 mg, 0.27 mmol), EDCI (97 mg, 0.49 mmol) and N-methylimidazole (60 mg, 0.735 mmol) in 10 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (5 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with a mixture of CH2Cl2 and methanol (100:1: to 20:1, V/V) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxamide (25 mg, 19%) as white solid. 1H NMR (300 MHz, DMSO): delta 9.57 (s, 1H), 8.81 (s, 1H), 8.475-8.46 (m, 1H), 8.27-8.25 (m, 2H), 7.60-7.25 (m, 2H), 6.92 (d, 1H, J=8.7 Hz), 6.47-6.39 (m, 3H), 4.54-4.52 (m, 1H), 3.76-3.58 (m, 10H), 2.27-2.05 (m, 2H). LC-MS: 247 [M/2+H]+, 493 [M+H]+, 491 [M-H]-, tR=1.22 min. HPLC: 95.20% at 214 nm, 95.06% at 254 nm, tR=5.64 min.

The synthetic route of 23814-14-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O3, 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. HPLC of Formula: C8H6N2O3

To a stirred solution of 2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carboxylic acid56 150 mg) and methyl indoline-4-carboxylate114 (149 mg) in methanol (5 ml) was added 4-(4,6- dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride 115 (280 mg, DMTMM). The reaction muxture was stirred for 4 h at room temperature. LC/MS analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC (Gemini NX CI 8, 12 nm, 5mu, 100 x 30 mm, flow rate 40 ml/min, eluant: CH3CN/H2O containing formic acid) followed by lyophilisation in vacuo to afford methyl l-(2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carbonyl)indoline-4-carboxylate (60 mg, 21%) as a white solid. MS (ISP): 338.1 ([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 23814-14-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-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 23814-14-4, Safety of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

To a stirred solution of 2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carboxylic acid (70 mg), l-(piperazin-l-yl)ethanone84 (50.4 mg) and N,N-diisopropylethylamine (206 mu) in DMF (1 ml) was added HATU (224 mg). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC (Gemini NX CI 8, 12 nm, 5mu, 100 x 30 mm, flow rate 40 ml/min, eluant: CH3CN/H2O containing formic acid) followed by lyophilisation to afford 5-(4-acetylpiperazine- l-carbonyl)-lH-benzo[d]imidazol-2(3H)-one (50 mg, 44%) as white solid. MS (ISP): 289.1 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem