Category: 16042-25-4

Synthetic Route of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 suspension of 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

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

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, A common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

To a stirred suspension of 1H-imidazole-2-carboxylic acid (3.00 g, 26.8 mmol) in anh. DCM (45 mL)cooled to 0 C under N2 was added oxalyl chloride (4.5 mL, 53.5 mmol) followed by addition of DMF (2 drops). The reaction was allowed to warm to rt and stir overnight. A further portion of oxalylchloride (1.13 mL, 13.4 mmol) and DMF (1 drop) was added and the reaction stirred for 4 hr.Volatiles were then removed in vacuo and the residual oxalyl chloride was removed by coevaporationwith toluene to afford acid chloride as a colourless solid. The solid was then addedportionwise to conc NH4OH (15 mL) chilled to 0 C. Volatiles were then removed in vacuo.Residual volatiles were coevaporated with toluene to obtain dry material (25: 75 startingmaterial:product). The crude was retreated to the reaction with oxalyl chloride (1.7 mL, 20.1 mmol)using the above procedure. The solid obtained was then washed with water (2 x 20 mL) and driedin vacuo to obtain a tan solid (2.16 g, 73%) that was used without further purification. LCMS (Waters Atlantis: Gradient Method 2): Rt = 1.44 min, 99 A% 254 nm, [M + H]+ = 112.2. 1H NMR(600 MHz, DMSO-d6) delta 12.95 (s, 1H), 7.73 (s, 4H), 7.43 (s, 1H), 7.23 (br s, 1H), 7.04 (br s, 1H).

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; Jarrad; Debnath; Miyamoto; Hansford; Pelingon; Butler; Bains; Karoli; Blaskovich; Eckmann; Cooper; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 353 – 362;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic 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 16042-25-4, Recommanded Product: 16042-25-4

General procedure: Ligand 1 was prepared by refluxing equimolar solution of imidazole- 2-carboxylic acid (0.112 g; 1 mM) and benzhydrazide (0.136 g; 1 mM) (HL1) in 50 mL of methanol. After 24 h, the reaction mixture was cooled to room temperature and the product formed was filtered, washed several times with water and then recrystallized from methanol to afford the desired product in pure form. Other Ligands 2-4 (HL2-HL4) were also prepared by adopting the similar procedure as in the caset of ligand, using the respective hydrazides i.e., isonicotinic acid hydrazide (0.137 g; 1 mM), furoic acid hydrazide (0.126 g; 1 mM) and thiophene-2-carboxylic acid hydrazide (0.142 g; 1 mM as summarized in Scheme 1.

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-Imidazolecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sathyadevi, Palanisamy; Krishnamoorthy, Paramasivam; Butorac, Rachel R.; Cowley, Alan H.; Dharmaraj, Nallasamy; Inorganica Chimica Acta; vol. 409; PART B; (2014); p. 185 – 194;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life. 16042-25-4

5 (1.00 g, 3.30 mmol) and 1H-imidazole-2-carboxylic acid(0.40 g, 3.60 mmol) were dissolved in 3 mL sulfolane, and 12 mLPOCl3 was added. The reaction mixturewas stirred at 85 C for 18 h,then cooled to room temperature, poured into 200 mL ice water.NaOH was added to adjust the PH to 7. The mixturewas filtered anddried in vacuo to give 92 mg of 11-3 as gray solid: 7% yield. 1H NMR(300 MHz, DMSO-d6) delta 13.83 (s, 1H), 8.77 (d, J = 5.4 Hz, 1H), 8.01 (d,J = 9.0 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J = 2.5 Hz, 1H), 7.28 (d, J =5.2 Hz,2H), 7.18 (dd, J= 9.2, 2.6 Hz, 1H), 5.82 (s, 2H), 3.90 (s, 3H); m.p.:205-207 C; HRMS (ESI+) m/z 380.0914 (380.0924 calcd forC17H14N7O2S+, [M+H]+).

The chemical industry reduces the impact on the environment during synthesis 16042-25-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Haoliang; Liu, Qiufeng; Zhang, Li; Hu, Shihe; Chen, Tiantian; Li, Huifang; Chen, Yadong; Xu, Yechun; Lu, Tao; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 491 – 502;,
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. 16042-25-4, name is 2-Imidazolecarboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 16042-25-4

HATU (0.16 g, 0.43 mmol) was added to a solution of 3-chloro-5-({6-chloro-2-fluoro- 3-[(methylamino)methyl]phenyl}oxy)benzonitrile (0.10 g, 0.30 mmol) and 1 H- imidazole-2-carboxylic acid (0.05 g, 0.43 mmol) in DMF (3 ml.) and the solution was stirred at RT overnight. After 16 h, ethyl acetate (100 ml) and saturated NaHCOs solution (100 ml) were added. The organic layer was separated, washed with saturated NaHCOs solution (2 x 100 ml), brine (150 ml_), dried over MgSO4, filtered and concentrated. The crude material was purified by Reverse Phase HPLC to give the title compound (0.025 g, 20%) as a white solid. 1H NMR (400 MHz, DMSO-c/6) delta ppm 7.82 (s, 1 H), 7.46 – 7.57 (m, 3 H), 7.27 – 7.37 (m, 2 H), 7.18 (s, 1 H), 5.57 (s, 1 H), 4.77 (s, 1 H), 3.53 (s, 1.5 H), 2.98 (s, 1.5 H). 19F NMR (376 MHz, DMSOd6) delta ppm -75.19 (s, 1 F). LCMS m/z 418 (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; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); 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. 16042-25-4, name is 2-Imidazolecarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Imidazolecarboxylic acid

The mixture of H3PMo12O40·26H2O (0.2g, 0.07mmol), AgNO3 (0.08g, 0.47mmol), and L1 (0.049g, 0.2mmol) was dissolved in 10mL of distilled water and stirred for 45mins at room temperature. The pH value was adjusted to 1.80 with 1.0molL-1 HNO3 (final pH 1.95). Then, the suspension was sealed into a Teflon-lined stainless steel autoclave (25mL) and kept under autogenous pressure at 160C for 3days. Slow cooling of the reaction mixture to room temperature, yellow block crystals were filtered and washed with distilled water (42% yield based on Mo). Elemental Anal. Calc. for C16H19Ag2N8O51PMo12 (2537.29): C 7.56, H 0.75, N 4.41. Found: C 7.60, H 0.72, N 4.39%

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16042-25-4.

Reference:
Article; Tian, Ai-Xiang; Hou, Xue; Ying, Jun; Liu, Guo-Cheng; Ning, Ya-Li; Li, Tian-Jiao; Wang, Xiu-Li; Inorganica Chimica Acta; vol. 439; (2016); p. 43 – 48;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, 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. 16042-25-4, name is 2-Imidazolecarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) yV-o-Tolyl-1W-imidazole-2-carboxamideTo a solution of 1 /-/-imidazole-2-carboxylic acid (0.52 g, 4.64 mmol) in DMF (20 mL) was added o-toluidine (0.50 mL, 4.64 mmol), EDC-HCI (1.35 g, 6.96 mmol) and HOBt (0.94 g, 6.96 mmol). The reaction mixture was stirred at room temperature for 16 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated to dryness. The crude product was purified by flash chromatography (2% to 3% MeOH/DCM) to yield 0.93 g (99%) of the title compound as a beige solid.LRMS (m/z): 202 (M+1 )+.

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

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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.

[00535] lH-Imidazole-2-carboxylic acid { 3-r4-(6-cyclohexylamino-9H-purin-2-ylamino)-3-methylphenoxylpropyl|amide (C14): Diisopropylethyl amine (0.10 g, 0.81 mmol) was added to a solution of lH-imidazole-2-carboxylic acid (0.025 g, 0.22 mmol), N- 2-[4-(3-aminopropoxy)-2-methyl-phenyl]-N-6-cyclohexyl-9H-purine-2,6-diamine (0.08 g, 0.20 mmol), EDCI (0.046 g, 0.24 mmol), and HOBt (0.037 g, 0.24 mmol) in DMF (1.0 mL), and the resulting mixture was stirred overnight at ambient temperature. The solvent was removed and the crude material was purified by reverse-phase HPLC to provide compound (Table 1, C14).

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MYRIAD PHARMACEUTICALS, INC.; KUMAR, Dange, Vijay; MCALEXANDER, Ian, A.; BURSAVICH, Matthew, Gregory; HOARAU, Christophe; SLATTUM, Paul, M.; GERRISH, David, A.; LOCKMAN, Jeffrey, W.; JUDD, Weston, R.; SAUNDERS, Michael; PARKER, Daniel, P.; ZIGAR, Daniel, Feodore; KIM, In, Chul; WILLARDSEN, J., Adam; YAGER, Kraig, M.; SHENDEROVICH, Mark, D.; WILLIAMS, Brandi, L.; TARDIF, Keith, D.; WO2010/111406; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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. Computed Properties of C4H4N2O2

Example 130 (3.2 mg, 5.4 imol), 1H-imidazole-2-carboxylic acid (9.1 mg, 0.082 mmol) and DIEA (4.8 pi, 0.027 mmol) were dissolved in DMF (0.5 mL). HATU (2.07 mg, 5.44 imol) was added, and the reaction mixture was allowed to stir at rt for 2 h.The reaction mixture was concentrated, and the residue was purified by RP HPLC to provide the product (2.2 mg, 58%) as a clear glass (bis TFA salt). MS(ESI) m/z 455.3 (M+H)t ?HNMR(SOOMHz, CD3CN) oe 7.92(s, 1H), 7.87 (s, 1H), 7.57 (s, 2H), 7.17 (m, 3H), 6.80 (t, J=0.96 Hz, 1H), 5.45 (s, 2H), 4.65-4.92 (m, 2H), 4.29 (s, 2H), 3.65-3.99 (m,2H), 2.96 (t, J=5.91 Hz, 2H). Analytical HPLC: RT = 3.34 mm (Method A).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

The imidazole-2-carboxylic acid (10 g, 89.2 mmol) in suspension in thionyl chloride (160 mL) was heated to reflux, under agitation for 18 h. The reaction mixture was cooled, then filtered, washed with toluene, and dried under high vacuum to obtain a yellow solid (yield, 80-85%). M.p.: 164 C. 1H NMR (300 MHz, DMSO-d6) delta: 8.85 (s, 2H); 8.2 (s, 2H). 13C NMR (300 MHz, DMSO-d6) delta: 145.85, 144.95, 125.20, 120.15.

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

Reference:
Article; Moarbess, Georges; Guichou, Jean-Francois; Paniagua-Gayraud, Stephanie; Chouchou, Adrien; Marcadet, Olivier; Leroy, Fiona; Ruedas, Remi; Cuq, Pierre; Deleuze-Masquefa, Carine; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 268 – 274;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem