Category: imidazoles-derivatives

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. 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, A new synthetic method of this compound is introduced below., Formula: C25H24N4O4

Methyl 2-ethoxy- l -((2′-(5-oxo-4,5-dihydro- l ,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- l H- benzo[< ]imidazole-7-carboxyiate of formula la - reproduction of the procedure (J. Med. Chem. 1996, 39(26), 5228-5235)2-ethylhexyl chloroformate (0.25 g, 2.6 mmol) was added to a stirred mixture of methyl 2- ethoxy- l -((2'-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)- l H-benzo[i/]imidazole-7- carboxylate (of formula Va; 1.16 g, 2.6 mmol), dry DMF (5 ml) and pyridine (0.22 g) under cooling in a water-ice mixture and the mixture was stirred at the temperature of 0C for 30 minutes. After dilution with water (20 ml) the mixture was extracted with ethyl acetate (4 x 10 ml), the extract was washed with water (4 x 5 ml) and dried with MgS04. The obtained evaporation residue ( 1.7 g) contained 92.2 % of the intermediate (of formula VI; R' = 2- ethylhexyl) according to HPLC. 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; ZENTIVA, K.S.; RADL, Stanislav; STACH, Jan; WO2012/139535; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 219814-29-6,Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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.

Step A : (5-Bromo-6-methyl-3 H- 1 ‘ -azaspiro [imidazo [2, 1 -b] oxazole-2,3 ‘ – bicyclo[2.2.2]octan]-l ‘-yl-8-ium)trihydroborate and (6-bromo-5-methyl-3H-l ‘- azaspiro[imidazo[2, l-b]oxazole-2,3 ‘-bicyclo[2.2.2]octan]- -yl-8-ium)trihydroborate To 2,4-dibromo-5-methyl-lH-imidazole (0.8 g, 3.3 mmol) in THF (25 niL) was added N-butyllithium (1.3 niL, 3.3 mmol) dropwise at -78C. After 45 minutes, a solution of racemic r-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-l’-yl-4- ium)trihydroborate (0.56 g, 3.7 mmol) from the reference example, in THF (20 mL) was added dropwise at -78C. The cooling bath was removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgS04, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield the regioisomeric products. These regioisomers were separated by reverse phase chromatography using a Sunfire column with gradients of acetonitrile-water containing 0.1% of trifluoroacetic acid (TFA), and at 40 mL/min flow rate. The pure fractions for peak 1 and peak 2 were then neutralized with 1 N NaOH (pH ~8-9) and the products were extracted with ethyl acetate. The organic layers were dried with MgS04, filtered and the solvent was removed to yield racemic (5-bromo-6-methyl-3H-l’-azaspiro[imidazo[2,l-b]oxazole-2,3′- bicyclo[2.2.2]octan]-l’-yl-8-ium)trihydroborate (0.32 g, 1.0 mmol, 30.8 % yield) XH NMR (500MHz, DMSO-d6) delta 4.23 (d, J=9.8 Hz, IH), 4.12 (d, J=9.9 Hz, IH), 3.36 (dd, J=15.2, 2.5 Hz, IH), 3.19 (dd, J=15.3, 2.1 Hz, IH), 3.04 – 2.95 (m, IH), 2.91 – 2.73 (m, 3H), 2.35 (br. s., IH), 2.03 – 1.88 (m, 4H), 1.84 – 1.67 (m, 3H), 1.64 – 1.11 (m, 3H). MS (LC/MS) R.T. = 2.09; [M+2]+ = 300.04 and racemic (6-bromo-5-methyl-3H-l’- azaspiro[imidazo[2,l-b]oxazole-2,3′-bicyclo[2.2.2]octan]-r-yl-8-ium)trihydroborate (0.33 g, 1.1 mmol, 31.7 % yield) as powders. NMR (500MHz, DMSO-de) delta 4.32 (d, J=10.1 Hz, IH), 4.12 (d, J=10.2 Hz, IH), 3.36 (d, J=2.4 Hz, IH), 3.18 (dd, J=15.2, 2.2 Hz, IH), 2.99 (d, J=2.9 Hz, IH), 2.93 – 2.78 (m, 3H), 2.31 (d, J=2.0 Hz, IH), 2.06 – 1.94 (m, 4H), 1.84 – 1.69 (m, 3H), 1.62 – 1.22 (m, 3H). MS (LC/MS) R.T. = 2.64; [M+2]+ = 300.04.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-methylimidazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; ZUSI, F. Christopher; HILL, Matthew D.; (87 pag.)WO2016/73407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3304-70-9

(1) Dimethyl 1H-imidazole-4,5-dicarboxylate (9.6 g, 52 mmol) was dissolved in acetonitrile (200 mE), and N-bromosuccinimide (13.92 g, 78 mmol) was added thereto, and then the mixture was stirred at 50 C. for 4 hours. After the reaction, water was added and the mixture was extracted twice with ethyl acetate. After being washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride, the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated to obtain dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate (8.3 g). This material was used as is in the next reaction without further purification:10217] ?H-NMR (CDC13) oe: 10.56 (1H, s), 3.96 (6H, s);10218] ESI-MS mlz=263 (M+H).

The synthetic route of 3304-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); 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

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

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

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

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

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

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