Author: Jessica.F

Synthetic Route of 39070-14-9,Some common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 solution of Compound i (1 g) in DMF (15 mL) was added N- bromosuccinimide (NBS, 1.25 g) and the reaction mixture stirred at 600C for 3h. Then the reaction mixture was diluted with brine, extracted with EtOAc, dried and concentrated to yield a residue that was separated by column chromatography using 0 – 80% EtOAc/Hexanes to yield Compound ii (1.3 g).

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; CHEN, Tao; WO2008/151253; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-16-5,Some common heterocyclic compound, 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, molecular formula is C8H7BrN2, 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 solution of intermediate 5 (2.5g, 11.8 mmol) in dioxane (100ml) were addedtributyl(vinyl)tin (5,2ml, 18 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.69g, O.Smmol) and the mixture was heated under reflux for 24 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2CI2/MeOH (95/5). The title compound was obtained as an oil (1.8g, 96.1percent); NMR H1 (300MHz, CDCI3, ppm) 5: 7.9 (s, 1H), 7.75 (d, 1H), 7.4 (m, 2H), 6.85 (dd, 1H), 5.8 (d, 1H), 5.25 (d, 1H), 3.85 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-1-methyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/111046; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 73746-45-9, A common heterocyclic compound, 73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, molecular formula is C4H5IN2, 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 solution of 160 mg (1.11 mmol) of 5-chloro-2-methyl-2H-pyridazin-3-one (CAS: [14628- 34-3]), 230 mg (1.11 mmol) of 4-iodo-2-methyl-lH-imidazole (CAS: [73746-45-9]), in 3.5 ml of dry DMF were added 721 mg (2.21 mmol) of cesium carbonate. The suspension was stirred for 30 min at 45C, then for 3h at 65C and allowed to cool. The cristallised product is filtered off, washed with ethyl acetate and dried in vaccuo to yield 250 mg (0.791 mmol, 71%) of the title compound as a crystalline light yellow solid, MS: m/e = 316.9 (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:
Patent; F. HOFFMANN-LA ROCHE AG; JAESCHKE, Georg; LINDEMANN, Lothar; VIEIRA, Eric; WICHMANN, Juergen; WO2011/6910; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 75370-65-9,Some common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H7N3O, 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.

Amine 2c (500 mg, 1.9 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (580 mg, 2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (265 mg, 1.78 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 140 mg of a pale yellow solid. Yield = 18% ‘HNMR (DMSO, 400 MHz) delta 1.54 (2H, m), 1.68 (4H, m), 2.85 (4H, m), 4.42 (2H, d, J = 6 Hz), 6.63 (1H, d, J = 7.6 Hz), 6.76 (1H, t), 6.84 (1H, t, J = 8.4 Hz), 6.95 (1H, d, J = 8.4 Hz), 7.31 (1H, s), 7.41 (1H, d), 7.52 (1H, d, J = 8.4 Hz), 8.33 (1H, s), 10.01 (1H, bs), 10.60 (1H, bs); [M+1] 434.1 1 (C2iH22F3N5O2 requires 433.43).

The synthetic route of 75370-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O2

d) 3-(7-Cyano-isothiochroman-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 4-hydroxy-isothiochroman-7-carbonitrile (630 mg, 3.3 mmol) in THF (20 ml.) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 460 mg, 3.6 mmol), and triphenylphosphine (909 mg, 3.4 mmol). The reaction is cooled to 0 0C and diisopropyl azodicarbpxylate (0.66 ml_, 3.4 mmol) is added. The reaction is permitted to warm to room temperature and stirred until LC-MS analysis indicates complete consumption of 4-hydroxy- isothiochroman-7-carbonitrile. The reaction mixture is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the organic layer is dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1 :1) to provide 3-(7-cyano- isothiochroman-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 300.1 (M+H). 1H NMR (400 MHz, CDCI3) delta ppm 3.08 – 3.23 (m, 1 H), 3.32 (dd, J=14.4, 4.0 Hz, 1 H), 3.73 – 4.07 (m, 2 H), 3.91 (s, 3 H)1 6.46 – 6.61 (m, 1 H), 7.15 (d, J=8.1 Hz, 1 H), 7.46 (s, 1 H), 7.49 – 7.54 (m, 1 H), 7.56 (s, 1 H), 7.84 (s, 1 H). The HCI salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCI in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCI salt of 3-(7-cyano-isothiochroman-4-yl)-3H-imidazole-4-carboxylic acid methyl ester.

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; NOVARTIS AG; WO2008/76336; (2008); A2;,
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 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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.

Take 250ml three mouth flask,The raw amine 3 (1.00 g, 4.15 mmol) was placed,20 ml of water was added,The temperature of the reaction system was lowered to 0 C,0.23 g of HCl was diluted in 5 ml of water and added dropwise to the reaction system,With the addition of HCl,The viscosity of the reaction system is increasing,So we carry out this step reaction is best to use mechanical stirring,After completion of the dropwise addition, stirring was continued at 0 C for 1 hour,Further, 20 ml of an aqueous solution of 0.28 g of sodium nitrite was added to the reaction system,Stirring was continued for 0.5 h.The above reaction solution system was added to KI (0.83 g) at 0 C,CuI (0.97 g) in 20 ml of water,Plus completed,The whole reaction system was gradually heated to 75 C,The reaction system has a bubble,Nitrogen gas is generated,When bubbles are no longer generated,To the reaction system, 50 ml of ethyl acetate was added to extract the product,The reaction process yield is not high,The reason for this is that the diazonium salts produced by Compound 3 are unstable,With the increase of temperature,Some of the diazonium salts have not decomposed before the iodide ion has been replaced.Too pure silica gel column,Compound 4 was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; Tianjin International Joint Academy of Biomedicine; Rao, Zihe; Yang, Cheng; Chen, Yue; Bai, Cuigai; Sun, Tao; Pan, Chengwen; Meng, Fanfei; Li, Yongtao; Wang, Jinghan; Jiang, Yin; (41 pag.)CN106188005; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, category: imidazoles-derivatives

2- hydroxymethyl-l -methyl-1 H-benzimidazole (Compound 49a)A suspension of l -methyl-2-formyl-l H-benzimidazole (500 mg, 3.12 mmol) and NaBH4 (134 mg, 3.43 mmol) in anhydrous THF (25 ml) was stirred for 24 hours at r.t.. The reaction mixture was quenched with water, extracted with EtOAc, dried over Na2S04 and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (Horizon.(R).TM – Biotage) eluting with CHC13 – 1.7M NH3 sol. in MeOH 100:2 giving the title product as white solid. Yield: 50.4 percent. MS: [ +H]+ = 163.5

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; RECORDATI IRELAND LIMITED; LEONARDI, Amedeo; MOTTA, Gianni; RIVA, Carlo; GUARNERI, Luciano; GRAZIANI, Davide; MARINONI, Fabio; BETTINELLI, Ilaria; WO2011/29633; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, 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 120781-02-4, SDS of cas: 120781-02-4

Methyl 2-(4-(hydroxymethyl)phenyl)-1-methyl-1H-imidazole-5-carboxylate (44). To a solution of methyl2-bromo-1-methyl-1H-imidazole-5-carboxylate5 (515 mg, 2.35 mmol, 1.0 eq) in dioxane (72 mL) was added Pd(PPh3)4 (133 mg, 0.115 mmol, 0.049 eq). The mixture was stirred for 15 min at room temperature before 4-hydroxymethylbenzeneboronic acid (357 mg, 2.35 mmol, 1.0 eq) in 22 mL H2O and K2CO3 (390mg, 2.82 mmol, 1.2 eq) were added. The reaction mixture was heated to 60 C and stirred for 16 h. The solvent was evaporated and the residue was diluted with EtOAc and H2O. The phases were separated and the product was extracted with EtOAc (3x 20 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (10-100% EtOAc linear gradient in hexanes) providing the corresponding benzylicalcohol in 81% (470 mg) 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, Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fuerst, Rita; Yong Choi, Jun; Knapinska, Anna M.; Smith, Lyndsay; Cameron, Michael D.; Ruiz, Claudia; Fields, Gregg B.; Roush, William R.; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4984 – 4995;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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. COA of Formula: C4H5BrN2

Intermediate 7: Step b (1-Methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone To a solution of 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 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.; US2015/105369; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem