Imidazoles-derivatives

Application of 35203-44-2,Some common heterocyclic compound, 35203-44-2, name is 1-Propyl-1H-imidazole, molecular formula is C6H10N2, 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.

A 100-mL two-neck flask was placed, N-propylimidazole (2.10 g, 18.0 mmol) and 35 mL of toluene were added, and 3-bromopropyldiethoxyphosphine oxide (5.18 g, 20.0 mmol) was added dropwise with heating and stirring.And reacted at 85 ¡ãC for 6 h and cooled to room temperature. Pour out the upper toluene,100 mL of deionized water was added to dissolve the product to obtain an aqueous phase. The aqueous phase was washed with an EtOAc_PE=3:1 organic phase (30 mL¡Á4) to separate the aqueous phase II; di(2-ethylhexyl) phosphate (P204). ) (5.80 g, 18.0 mmol) was refluxed under the action of sodium for 24 h. The resulting sodium salt was dissolved in methylene chloride and the separated aqueous phase was stirred at room temperature for 3 h.Add 50 mL of CH2Cl2 and stir to separate the organic phase. The organic phase was washed with deionized water (20 mL¡Á5) and the organic phase was obtained after liquid separation. The organic phase was dried by adding anhydrous Na 2 SO 4 , filtered, and most of the CH 2 Cl 2 was evaporated under reduced pressure and dried in vacuum at 70¡ã C. for 3 h. Yellow sticky liquid product 9.45g (yield 86percent),

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Propyl-1H-imidazole, its application will become more common.

Reference:
Patent; Ningbo University; Wang Junping; Liang Hongze; Feng Da; Zhao Jieying; Kang Xinchun; Zhang Xiaozhen; Shen Fei; Huang Feilong; (21 pag.)CN104945435; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 128293-62-9,Some common heterocyclic compound, 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H11N3O2, 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 231: N-[2-(tert-butylcarbamoyl)-1-methyl-1H-imidazol-4-yl]-4,4-dimethyl- l-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxamide Step 1: Synthesis of ethyl 4-{[(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2- a]indol-7-yl)carbonyl]amino}-1-methyl-1H-imidazole-2-carboxylateTo a solution of 4,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7- carboxylic acid (336 mg, 1.3 mmol, Intermediate E) in DMF (1 mL) are added N- hydroxybenzotriazole (351 mg, 2.6 mmol) and l-ethyl-3-(3-dimethylaminopropyl) carbodiimide (498 mg, 2.6 mmol). After stirring for 10 min, 4-amino-1-methyl-lH- imidazole-2-carboxylic acid ethyl ester (535 mg, 2.6 mmol), N,N-diisopropylethylamine (0.45 mL, 2.6 mmol) and 4-dimethylaminopyridine (32 mg, 0.26 mmol) are added. The reaction mixture is heated at 60 C for 16 h. DMF is removed under a stream of N2 at 40 C and EtOAc (2 mL) and water (2 mL) are added. After stirring for 15min, a white solid is formed and it is filtered and dried to afford the title compound (490 mg, 92%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17464-88-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17464-88-9 name is 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

60 g (0.188 mol) of tetramethoxymethylglycoluril (product name: POWDERLINK [registered trademark] 1174 commercially available from Japan Cytec Industries, hereinafter abbreviated as PL-LI in this specification), 1,200 g of propylene glycol monomethyl ether (hereinafter abbreviated as PGME in this specification), and 120 g of a washed ion-exchange resin for a catalyst (product name: AMBERLYST [registered trademark] 15JWET, commercially available from Dow Chemical Company, hereinafter abbreviated as 15JWET in this specification) were put into a 2,000 mL flask, and the mixture was stirred and dissolved at 25¡ã C. and then heated and stirred under a reduced pressure (80 Torr to 100 Torr) at 60¡ã C. for 7 hours. Then, the pressure inside the flask was recovered and cooling was performed to 25¡ã C., and then 15JWET was filtered off to obtain a desired compound (hereinafter abbreviated as PGME-PL in this specification). The obtained compound was identified by 1H NMR. As a result, it was confirmed that a peak (31.9 ppm) of a methoxy group of PL-LI disappeared and about 4 molecules of PGME were introduced into one molecule of PL-LI, and the glycoluril derivative of Formula (1A-1) (hereinafter abbreviated as PGME-PL in this specification) was obtained. [1.0 to 1.1 ppm (3H, ?CH3), 3.2 to 3.3 ppm (20H, ?OCH3 and ?CH2O?), 3.6 to 3.8 ppm (4H, ?OCH<)] At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,4,6-Tetrakis(methoxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, and friends who are interested can also refer to it. Reference:
Patent; NISSAN CHEMICAL CORPORATION; SAKAIDA, Yasushi; TAKASE, Kenji; KISHIOKA, Takahiro; SAKAMOTO, Rikimaru; (14 pag.)US2019/163063; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1, These common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-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.

a solution of 9.5 g of ethyl imidazole-2-carboxylate, 9.9 g of 2,5-dibromo-1-indanone and 0.1 g of sodium iodide in 280 ml of ethanol is kept boiling for 16 hours, cooled to 20¡ã C. and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50¡ã C. The product obtained (21 g) is dissolved in 50 ml of dichloromethane and the solution is washed 3 times with a total of 600 ml of distilled water, dried over anhydrous magnesium sulphate and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50¡ã C. The product obtained (12.7 g) is chromatographed on 790 g of neutral silica gel (0.020-0.045 mm) contained in a column 7 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 75-ml fractions. Fractions 70 to 140 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40¡ã C. 3.7 g of ethyl 1-(5-bromo-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 140¡ã C. The 2,5-dibromo-1-indanone can be prepared as described in European Patent 346107.

Statistics shows that Ethyl 1H-imidazole-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 33543-78-1.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 45676-04-8,Some common heterocyclic compound, 45676-04-8, name is 1-tert-Butylimidazole, molecular formula is C7H12N2, 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.

This ligand was prepared according to a literature method [15] with slight modifications. A mixture of 2,6-dichloropyridine (1.5g, 10mmol) and 1-tert-butylimidazole (5.0g, 40mmol) was heated in an autoclave at 150C for 3 days. Upon cooling, the reaction mixture was dissolved in MeOH (5mL), followed by addition of a large amount of diethyl ether. After filtration, the precipitate was washed with acetone (20mL) and dried to give 2,6-bis(3-tert-butylimidazolium-1-yl)pyridine dichloride as an off-white solid (2.7g, 68%). 1H NMR (CD3CN): delta 10.37 (brs, 2H, NCHN), 8.97 (brs, 2H, imid), 8.58 (t, J=8.1Hz, 1H, 4-py), 8.46 (d, J=8.0Hz, 2H, 3,5-py), 8.36 (brs, 2H, imid), 1.72 (s, 18H, tBu). ESI-MS (m/z): 360.4 [M-Cl]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-tert-Butylimidazole, its application will become more common.

Reference:
Article; Nakamura, Takuo; Ogushi, Shinji; Arikawa, Yasuhiro; Umakoshi, Keisuke; Journal of Organometallic Chemistry; vol. 803; (2016); p. 67 – 72;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1008361-65-6, name is 5-Bromo-6-methoxy-1H-benzo[d]imidazole, 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 1008361-65-6, Product Details of 1008361-65-6

Compound 5-bromo-6-methoxy-1H-benzimidazole 60d (430.0 mg, 1.9 mmol), triethylamine (383.0 mg,3.8 mmol) and 4-dimethylaminopyridine (23.0 mg, 0.2 mmol)With tetrahydrofuran (15.0 mL)After mixing, di-tert-butyl dicarbonate (585.0 mg, 2.9 mmol) was added at room temperature, and the reaction was carried out at 45 C for 12 hours.The reaction solution was diluted with methylene chloride (100 mL) and washed with brine. The organic phase is dried over anhydrous sodium sulfate and filtered to dissolve to give a mixture of 1-t-butoxy acyl-5-Bromo-6-methoxy-benzimidazole 60e and 3-tert-butoxycarbonyl-5-bromo-6-methoxy-benzimidazole 61e (450.0 mg,1.4 mmol, white solid), yield 73%.

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, 5-Bromo-6-methoxy-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Tianyinjianhua Pharmaceutical Technology Co., Ltd.; Kong Xianglong; Zhou Chao; Zheng Zhixiang; (105 pag.)CN109020957; (2018); A;,
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. 256519-11-6, name is 2-Chloro-7-fluoro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Formula: C7H4ClFN2

A mixture of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5- (piperidin-3-yl)benzofuran-3-carboxamide (80 mg, 0.174 mmol), 2-chloro-4-fluoro-1H-benzo[d]imidazole (47.5 mg, 0.279 mmol) and triethylamine (90 mg, 0.696 mmol) in DMF (1 ml)was heated to 170C for 40 mm. The reaction mixture was cooled to RT and partitioned between EtOAc and water. The organic layer was dried in Na2SO4 and concentrated under vacuum. Then the reaction mixture separated by SFC on a ChiralPark AD, 3×25 cm, 40% MeOH(0.1%NH3.H20)/C02 to afford Example 55 (Enantiomer 1, peak 1 on SFC, HPLC_RT=3.91mm) as white solid 5 mg (10%) (LC-MS (ES, mlz) C30H29F2N5045: 593; Found: 594 [M+H]b) and Example 56 (Enantiomer 2, peak 2 on SFC, HPLC_RT=6.34 mm) as white solid 5 mg (10%) (LCMS (ES, mlz) C30H29F2N504S: 593; Found: 594 [M+Hf).

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; MERCK SHARP & DOHME CORP.; HE, Shuwen; LAI, Zhong; DAI, Xing; XIAO, Dong; LONDON, Clare; ZORN, Nicolas; NARGUND, Ravi; PALANI, Anandan; MCCOMAS, Casey C.; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/205592; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 616-47-7, A common heterocyclic compound, 616-47-7, name is 1-Methyl-1H-imidazole, molecular formula is C4H6N2, 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.

General procedure: The ionic liquids used in this study (Fig. 1) were synthesized as described in the literature [23,24]. IL-1, for example, was prepared as follows: 1-methylimidazole (16.4g, 0.2mol) and 1, 4-butanesultone (27.28g, 0.2mol) were mixed in a 100mL round bottom flask. The mixture was stirred at 42-45C for 17h. The white solid zwitterion was washed repeatedly with ether to remove non-ionic residues, filtrated through a Buchner funnel, and dried in vacuum for 4h. A stoichiometric amount of trifluoroacetic acid (22.8g, 0.2mol) was added dropwise, and the mixture was stirred for 6h at 80C. The viscous liquid was washed three times with ether and dried in vacuum to form IL-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:
Article; Tao, Fu-Rong; Zhuang, Chen; Cui, Yue-Zhi; Xu, Jing; Chinese Chemical Letters; vol. 25; 5; (2014); p. 757 – 761;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

EXAMPLE 1; [4-(1-{3-[2-(3-phenylsulphonylamino-phenyl)-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-imidazol-4-yl)-phenyl]-acetic acid-hydrotrifluoroacetate; a. Tert-butyl [3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propyl]-carbamate; 3.88 g (20 mmol) 4-iodoimidazole are dissolved in 30 ml DMPU and at 5 C., 556 mg (22 mmol) 95% sodium hydride are added batchwise. After the development of gas has died down the reaction mixture is stirred for 1 hour at 10 C. Then a solution of 4.44 g (20 mmol) tert-butyl (3-chloro-1,1-dimethyl-propyl)-carbamate in 5 ml DMPU and 739 mg (2.0 mmol) tetrabutylammonium iodide are added. The reaction mixture is stirred for 16 hours at ambient temperature and then heated to 80 C. for 24 hours. After cooling to ambient temperature the reaction solution is poured onto a mixture of 500 ml ice water and 250 ml of ethyl acetate. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are washed with water and saturated aqueous sodium chloride solution, dried on sodium sulphate and evaporated down using the rotary evaporator. The residue is chromatographed on silica gel (petroleum ether/ethyl acetate=80:20?0:100).Yield: 1.66 g (22% of theory)C13H22IN3O2 (379.24)Mass spectrum: (M+H)+=380Rf value: 0.45 (silica gel; petroleum ether/ethyl acetate=1:1)

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Walter, Rainer; Trieselmann, Thomas; Netherton, Matthew R.; Santagostino, Marco; Hamilton, Bradford S.; US2008/300290; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 24155-42-8, A common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, molecular formula is C11H10Cl2N2O, 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.

EXAMPLE 5 2-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:2) 3.2 g of 2-Chloromethylquinoline hydrochloride (0.015 mol) (commercially available), 3.85 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 14.8 g sodium hydroxide (0.37 mol) in 25 ml of water, 0.25 g of benzyltrimethylammonium chloride and 40 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up, the oily product (6.4 g) is dissolved in 150 ml of ether, charcoaled and then etheral hydrochloric acid is added to the clear solution while stirring. The precipitated hydrochloride (5.8 g) is filtered off, washed with ether and hexane and recrystallized from acetonitrile; m.p. 148-149 C. The following additional products of formula D or E are obtained by the procedure of Example 1 by reacting the unsubstituted or substituted 1-phenyl-2-(1H-imidazol-1-yl)ethanol of formula A with the unsubstituted or substituted 2-chloromethylquinoline of formula B or the unsubstituted or substituted 4-chloromethylquinoline of formula C. The substituents apply to the respective formulae.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4282230; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem