Month: July 2021

Reference of 17325-26-7, 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

b) 3-(2,2-Dimethyl-3-oxo-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 3-hydroxy-2,2-dimethyl-indan-1-one (2.0 g, 11.3 mmol) in THF (50 mL) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.72 g, 13.6 mmol), and triphenylphosphine (3.56 g, 13.6 mmol). The reaction is cooled to 0 0C and di-f-butyl azodicarboxylate (3.13 g, 13.6 mmol) is added. The reaction is placed at room temperature and permitted to stir for three hours. The reaction mixture is cooled to 0 0C and quenched with 4 N HCI in dioxane (5 mL, 20 mmol) and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCI. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 3:7) to furnish 3-(2,2-dimethyl- 3-oxo-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; HRMS: (ESI) m/z 285.1246 [(M+H)+: Calcd for C16H16N2O3: 285.1239]; 1H NMR (400 MHz, CDCI3) delta ppm 0.82 (s, 3 H), 1.46 (s, 3 H), 4.02 (s, 3 H), 6.70 (s, 1 H), 7.39 (s, 1 H), 7.47 – 7.52 (m, 1 H), 7.72 (t, J=7.45 Hz, 1 H), 7.79 – 7.86 (m, 1 H), 7.93 – 7.99 (m, 2 H).

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

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 5805-57-2,Some common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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.

General procedure: 9-Chloroacridine or its derivatives (1.0 mmol) and phenol (10.0 mmol) were added into a 100 ml round-bottom flask and the mixture was stirred for 1 h at 60 C under argon atmosphere. Then benzimidazole derivatives (8a-8n, 8p-8q, 1.2 mmol) were added. The mixture was stirred under 120 C for 2 h. Then the mixture was poured into a mixture of ethyl acetate (50 mL) and N-methyl morpholine (1 ml) to get the crude product as yellow precipitation. The crude product was recrystallized from ethylacetate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1H-Benzo[d]imidazol-2-yl)methanamine, its application will become more common.

Reference:
Article; Gao, Chunmei; Li, Bin; Zhang, Bin; Sun, Qinsheng; Li, Lulu; Li, Xi; Chen, Changjun; Tan, Chunyan; Liu, Hongxia; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1800 – 1807;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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. Computed Properties of C4H4N2O

Preparation 5 1-Trityl-1H-imidazole-4-carboxaldehyde A solution of trityl chloride (9.5 g, 34.3 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to an ice-cooled solution of imidazole-4-carboxaldehyde (3 g, 31.2 mmol) and triethylamine (17 ml, 125 mmol) in N,N-dimethylformamide (30 ml) and the solution was stirred for 2 hours. The reaction was then allowed to warm to room temperature, and was stirred for a further 18 hours. Water (200 ml) was added, and the resulting pink solid was collected and dried, then dissolved in dichloromethane (200 ml). The resulting solution was washed with water (2*100 ml), dried (MgSO4) and evaporated under reduced pressure. The product was recrystallized from ethanol to afford the title compound as a solid, 7.8 g. 1H-NMR (CDCl3, 400 MHz) delta: 7.06 (m, 6H), 7.32 (m, 9H), 7.48 (s, 1H), 7.58 (s, 1H), 9.82 (s, 1H). Microanalysis found: C, 81.54; H, 5.37; N, 8.24. C23H18N2O requires C, 81.63; H, 5.36; N, 8.28%.

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

Reference:
Patent; Pfizer Inc.; US2003/199522; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, 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. Safety of Methyl benzimidazole-5-carboxylate

The benzimidazole -5 – methyl formate (2.66 g, 15 . 12 mmol) is dissolved in 35 ml ethanol, adding hydrazine hydrate (8.6 ml, 120.9 mmol), 80 C reflux reaction for 36 hours, filtering, to obtain white solid, then the beating of ethyl acetate three times (3 × 15 ml), to obtain 1.8 g of white solid, yield 67.7%

The synthetic route of Methyl benzimidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Wang Xiaojian; Sun Chenbin; Ge Jun; Xi Meiyang; Xiao Qiong; Yin Dali; (51 pag.)CN107151220; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) imidazo [1,2- a] pyridine(100 mg, 0.31 mmol),Palladium acetate (4 mg, 0.016 mmol),Triphenylphosphine (16 mg, 0.06 mmol),And sodium carbonate (66 mg, 0.62 mmol)After adding 1,4-dioxane and water at a ratio of 1: 1 in 2 mL portions2-Bromobenzimidazole (61 mg, 0.31 mmol) was added thereto, and the mixture was stirred at 90 ° C for 16 hours. After the reaction is completed, the reaction mixture is cooled to room temperature and the reaction product is separated into water and ethyl acetate. The extracted organic layers were concentrated and the concentrate was purified by silica gel column chromatography (dichloromethane: ethyl acetate, 10: 1 v / v) to give 2- (3- (imidazo [ ) Phenyl) -1H-benzimidazole (43 mg, 45percent).

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

Reference:
Patent; Korea Research Institute of Chemical Technology; Jeon Mun-guk; Kim Gwang-rok; Huh Yun-jeong; Lee Jun-mi; (27 pag.)KR2018/101671; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 120781-02-4, These common heterocyclic compound, 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, 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 1-[4-(4,4,5,5-tetramethyl)-[1,3,2]-dioxaborolan-2-yl]-benzyl-1H-benzoimidazole (0.527 g, 1.5 mmol) and 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (Anichem LLC, 0.328 g, 1.5 mmol) in anhydrous DMF (5 mL) under nitrogen was added Pd(dppf)2Cl2 (53 mg, 0.065 mmol) and cesium carbonate (0.786 g, 2.4 mmol) and the reaction mixture was heated to 80 C. and allowed to stir for 7 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and the solids filtered off. The filtrate was washed with water, dried (Na2SO4) and the solvent removed under reduced pressure. Purification by flash chromatography (silica, dichloromethane/methanol 99: 1?97:3) provided the title compound (40%). LCMS (ESI+) 347.2 (MH+).

Statistics shows that Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 120781-02-4.

Reference:
Patent; Wyeth; US2009/23707; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, name is 4-(Trifluoromethyl)-1H-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. Computed Properties of C4H3F3N2

To a 0 C. solution of 4-(trifluoromethyl)-1H-imidazole (1.82 g, 13.4 mmol) in DMF (20 mL) was added sodium hydride (0.81 g, 20.1 mmol). The mixture was stirred at room temperature for 1 h. The crude 2,6-dimethyl-4-nitrophenyl trifluoromethanesulfonate prepared above (4.0 g, 13.4 mmol) was added. The mixture was stirred at 80 C. for 12 h. The reaction was diluted with water and extracted with ethyl acetate (30 mL*3). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 1-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole (805 mg, 21%) as a colorless solid. 1H NMR (400 MHz, CDCl3) delta 8.01 (s, 2H), 7.47 (s, 1H), 7.23 (s, 1H), 2.11 (s, 6H).

The synthetic route of 33468-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; US2012/202834; (2012); 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. 930-62-1, name is 2,4-Dimethylimidazole, A new synthetic method of this compound is introduced below., Computed Properties of C5H8N2

Example 0698 A mixture of tris(dibenzylideneacetone)dipalladium(0) (27 mg), 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (29 mg), tripotassium phosphate (96 mg), and toluene (1.5 mL) was stirred at 110 C. for 5 minutes in a nitrogen atmosphere. 7-Bromo-N-(5-isopropylpyridazin-3-yl)-1,5-naphthyridine-2-amine (50 mg) and 2,4-dimethyl-1H-imidazole (43 mg) were added to the reaction mixture, followed by stirring at 110 C. for 4 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained residue was purified sequentially by silica gel column chromatography (hexane-ethyl acetate-methanol), preparative thin layer silica gel column chromatography (chloroform-methanol, NH silica), and preparative thin layer silica gel column chromatography (chloroform-methanol), thereby obtaining 7-(2,4-dimethyl-1H-imidazol-1-yl)-N-(5-isopropylpyridazin-3-yl)-1,5-naphthyridine-2-amine (10 mg) as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 10.87 (1H, s), 8.87 (1H, d, J=1.8 Hz), 8.82 (1H, d, J=1.8 Hz), 8.33 (1H, d, J=9.0 Hz), 8.31 (1H, brs), 8.22 (1H, brs), 7.82 (1H, d, J=9.0 Hz), 7.21 (1H, s), 3.10-2.95 (1H, m), 2.34 (3H, s), 2.08 (3H, s), 1.30 (6H, d, J=6.6 Hz). MS m/z (M+H): 360.

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1467-16-9, name is 1H-Imidazole hydrochloride, 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 1467-16-9, name: 1H-Imidazole hydrochloride

A mixture of lithium(1+) ion 3-amino-5H-pyrrolo[2,3-£>]pyrazine-2-carboxylate, Intermediate 3 (5.00 g, 27.2 mmol), CDI (6.61 g, 40.7 mmol) and 1 /-/-imidazole hydrochloride (1 :1) (3.12 g, 29.9 mmol) in DMF (80 ml) was stirred at RT for 16 h. Additional CDI (2.00 g, 12.3 mmol) was added and the reaction was left to stir for a further 1 h at RT. The reaction mixture was diluted with water (350 ml) then stirred at RT for 5 min then left to stand at RT for 0.5 h. The resultant mixture was filtered then the collected solid was washed with water then dried under vacuum to afford the product as a yellow/orange solid (3.30 g, 52%). 1 H NMR (500 MHz, DMSO-cfe) delta 11.69 (s, 1 H), 8.74 (t, J = 0.9 Hz, 1 H), 7.94 (t, J = 1.4 Hz, 1 H), 7.63 (dd, J = 3.8, 2.3 Hz, 1 H), 7.44 (s, 2H), 7.08 (dd, J = 1.5, 0.8 Hz, 1 H), 6.52 (dd, J = 3.8, 1.3 Hz, 1 H). LC/MS (System A): m/z (ESI+) = 229 [MH+], Rt = 0.65 min, UV purity = 97%.

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, 1H-Imidazole hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 124750-92-1, 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. 124750-92-1, name is Losartan carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A m ixture of 2-buty I-4-ch loro- 1 – { [2′-( 1 H-tetrazol-5-yl)bipheny l-4-yl]methy 1 } – 1 H-imidazo.e-5 -carboxy I ic acid (Step A, Intermediate 4, 7.83 g, 16.5 mmol), isosorbide-5-mononitrate (1.55 g, 8.11 mmol), l-ethyl- 3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.78 g, 19.7 mmol), 1-hydroxybenzotriazole (1.25 g, 8.16 mmol), 4-dimethylaminopyridine (0.10 g, 0.82 mmol), and N-methylmorpholine (9.0 mL, 82 mmol) was dissolved in dichloromethane (150 mL) and stirred for 2 days. It was then concentrated in vacuo and purified by reversed-phase mass-directed etaPLC (Sunfire C-18) to afford the title compound. 1H NMR (500 MHz, CDCl3) delta 8.02 (dd, J = 7.6, 1.0 Hz, 1H), 7.61 (td, 7= 7.6, 1.3 Hz, 1H), 7.55 (td, J= 7.7, 1.1 Hz, 1H), 7.43 (d, J= 7.8 Hz, 1H), 7.18 (d, J= 7.7 Hz, 2H), 6.96 (d, J= 7.8 Hz, 2H), 5.5O (s, 2H), 5.40 (td, J= 5.4, 3.0 Hz, 1H), 5.32-5.30 (m, 1H), 4.99 (t, J= 5.2 Hz, 1H), 4.51 (d, J= 5.0 Hz, 1H), 4.06- 4.02 (m, 3H), 3.99 (dd, J= 1 1.4, 5.4 Hz, 1H), 2.68 (t, J= 7.7 Hz, 2H), 1.69 (quintet, J= 7.7 Hz, 2H), 1.36 (sextet, J= 7.5 Hz, 2H), 0.89 (t, J= 7.3 Hz, 3H); LC-MS: m/z 610.1 (M + H).

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, Losartan carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; NICOX S.A.; WO2009/140111; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem