Category: imidazoles-derivatives

Reference of 60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Mercapto-l-methylimidazol (40.8 mg, 0.35 mmol) was neat to a solution of l-bromo-3- (4-chloro-phenyl)-3-methyl-butan-2-one (98.5 mg, 0.35 mmol) in CH3CN (5 mL) at room temperature, then Et3N (0.098 mL, 0.70 mmol) was added neat to the mixture and the reaction was stirred overnight. Thiol residues were trapped by addition of a small spatula of resin 2-chlorotrityl chloride in 30 min then the mixture was filtered and concentrated under vacuum. The crude mixture was purified by flash chromatography (hexane/EtOAc gradient 0-40%) to give the expected compound (108.5 mg, 100%) as brown solid. TLC single spot at R/ 0.47 (MeOH/DCM 1:9); Mp = [43.7-47.3 0C]; 1H NMR (270 MHz, CDCl3): delta 1.46 (s, 6H), 3.59 (s, 3H), 3.86 (s, 2H), 6.84 (d, J = 1.1 Hz, IH), 6.94 (d, J = 1.4 Hz, IH), 7.07-7.15 (m, 2H), 7.23-7.30 (m, 2H); Accurate Mass: calculated (MVH) 309.0823; found 309.0811; HPLC tr = 2.06 min (100%) in 10% water-acetonitrile.

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, 1-Methyl-1H-imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; STERIX LIMITED; WO2009/106817; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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) resin swelling: 400 mg of Fmoc-protected phenylhydrazine resin (0.66 mmol / g, 0.264 mmol) and 3 mL of CH2CI2 were added to a 10 mL solid phase reactor, the resin was swollen for 30 min, CH2CI2 was withdrawn, (B) removal of Fmoc protecting group: A solution of 3 mL of 20% piperidine / DMF was added to the swollen resin in step (a) N2 was bubbled and mixed. After lOmin, the solvent was extracted, and then 3 mL of 20% piperidine / DMF solution was added. N2 was bubbled and mixed. After lOmin, the resin was washed with DMF (4X3mL) and the resin was washed with 3 mL of anhydrous DMF ,spare; (C) Amino acid condensation: 4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid (254 mg, 1.056 mmol) and triphosgene (BTC, 128 mg, 0.433 mmol) were dissolved in 2 mL of anhydrous THF, A large amount of white precipitate was immediately added to the reaction, and the reaction was further carried out for 3 min. Then, 2 mL of a solution of DIEA / DMF (5%, nu / nu) The reaction solution was transferred to the phenylhydrazine resin in which the protecting group was removed, N2 was bubbled and mixed, the reaction was carried out for 0.5 to 1 h, the reaction solution was extracted, and the resin was washed with DMF (4 X 3 mL) ,spare;(D) removal of tert-butoxycarbonyl protecting group: The mixture was washed with CH2C12 (2 X 3 mL), the CH2C12 was removed, and the tert-butyl group was removed by the addition of 3. OmL TFA / benzoic acid / Eta2Omicron (nu: nu: nu = 92: 5: 2.5) (2 × 3 3) and DMF (4 X) were added to the reaction mixture for 2 min, and then the solvent was extracted for 2 min, and then the mixture was stirred for 20 min with 3. OmL TFA / phenol / H20 (nu: nu: nu = 92: 5: 2.5) 3 mL) and the resin was washed with 3 mL of anhydrous DMF, The above-mentioned condensation and deprotection steps (c) and (d) were repeated until completion of the synthesis of the peptide on the phenylhydrazine resin represented by the formula (1) (E) condensing amino acids: 4-tert-butoxycarbonylamino-1-methyl -1H- imidazole-2-carboxylic acid (254mg, 1.056mmol) and triphosgene (BTC, 128mg, 0.433mmol) was dissolved in 2mL anhydrous of THF, to this solution was slowly added dropwise trimethyl pyridine (collidine, 488muL, 3.696mmol), the reaction to produce a heavy white precipitate immediately addition was complete the reaction 3min, added 2mLDIEA / DMF solution (5%, v / v), white the precipitate completely disappeared, the reaction solution was transferred to step (b) deprotection of the resin phenylhydrazine, N 2Bubbled mixing, the condensation reaction 0.5 ~ 1h, the reaction solution pumping, with DMF (4 × 3mL) resin was washed, to give formula (2) is supported on the peptide resin represented phenylhydrazine;A(G) solution of R-2-(9-fluorenylmethoxycarbonylamino)-4-tert-butoxycarbonylaminobutyric acid (465 mg, 1.056 mmol) and triphosgene (128 mg, 0.433 mmol) in 2 mL of anhydrous THF was added to the solution (48 mg) was added dropwise to a solution of HOAt (144 mg, 1.056 mmol) followed by addition of 2 mL of DIEA / DMF solution (5%, nu / nu), followed by the addition of trimethylpyrone (488 yL, 3.696 mmol) The reaction solution was transferred to a linear peptide (NH2-Im-Im-Py-Py-phenylhydrazine resin) supported on a phenylhydrazine resin represented by the formula (1), and the N2 pellet was completely removed. And the reaction was carried out with DMF (4 x 3mL) to obtain the peptide supported on the phenylhydrazine resin as shown in formula (3) (H)repeating the condensation and deprotection guard step (d) and (C), wherein the load until the completion of the synthetic peptides of formula (4) in the resin phenylhydrazine;(I)repeating the condensation and deprotection guard step (d) and (E), wherein the load until the completion of the synthetic peptides shown in formula (5) in the resin phenylhydrazine;(J)1-methyl -1H- imidazole-2-carboxylic acid (132mg, 1.056mmol) and PyBOP (550mg, 1.056mmol) was dissolved in dry 3mL of DMF, DIEA (350muL, 2.112mmol ), the reaction 5min, the reaction solution was transferred to a step (h) the load represented by the formula (4) in the resulting peptide resin phenylhydrazine, N2Mix bubbled condensation reaction 2h, the reaction solution pumping, with DMF (4 × 3mL) the resin was washed, and the procedure (b) The method of removing the load represented by the formula (5) phenylhydrazine peptide on the resin Fmoc protecting group, the peptide load of formula (6) in a phenylhydrazine of the resin;(K) Boc2O (243muL, 1.056mmol) was dissolved in dry 3mL of DMF, DIEA (350muL, 2.112mmol), transferring the reaction solution to remove the Fmoc formula (6) is supported on the peptide resin phenylhydrazine, N2Mix bubbled condensation reaction 20min. In addition to pumping load reaction solution with DMF (4 × 3mL) the resin was washed to give Boc protected compound of formula (7) phenylhydrazine peptide on the resin;

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

Reference:
Patent; Shenzhen Advanced Technology Institute; Su Wu; Wang Wei; Pan Zhengyin; Cheng Zhehong; Wu Chunlei; Fang Lijing; (36 pag.)CN106674209; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3543-73-5, 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. 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE-II Preparation of Ethyl 4-(5-(bis(2-Hydroxyethyl)Amino)-1-Methyl-1H-Benzo[d]-Imidazol-2-yl)Butanoate (Formula-IV) To a clean dry flask were charged compound of formula III (20 g), sodium carbonate (16.24 g), sodium Iodide (10.6 g) and 80 ml of 2-chloroethanol. The mixture was stirred for 5 minutes at room temperature and the reaction mass was heated to 65-70 C. and maintained for 8-12 hours. The mass was cooled to room temperature and pH adjusted to 1.0 using 6N HCl. The aqueous layer was extracted with ethyl acetate and the aqueous layer pH is adjusted to 8 to 9 using sodium carbonate solution. The Aqueous layer is extracted with dichloromethane and is distilled out completely and the solid obtained which is then purified in ethyl acetate to give 10 g of the title compound.

The synthetic route of Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOPHORE INDIA PHARMACEUTICALS PVT. LTD; Pullagurla, Manik Reddy; Rangisetty, Jagadeesh Babu; Presley, S. I. Davis; Nagarapu, Radha; US2013/317234; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Dimethyl sulfoxide (10 mE), 3-(4-methyl-1H-imi- dazole-1 -yl)-5-(trifluoromethyl) aniline (aromatic amine, 4.5 mmol), N-5-bromo-2-methylphenyl(4-(pyridine-3-yl) pyrimidine-2-amine (5.4 mmol), 1, 1?-bis(diphenylphos- phino)ferrocene-palladium (II) dichloride dichioromethane complex (0.135 mmol), triphenylphosphine (0.27 mmol), phenol (0.225 mmol), triethylamine (13.5 mmol) and a 4 A molecular sieve (1 g) are added into an autoclave for uniform stirring. Nitrogen is introduced to displace air, and then a carbon monoxide is introduced to displace the nitrogen to and the pressure in the autoclave is increased to 0.8 MPa. A temperature is increased by heating to 90-105 C. for reaction. Afier 72 h reaction, a product system containing an amination product is obtained. The product system is cooled to be below 50 C., and the carbon monoxide is evacuated and displaced with the nitrogen.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASYMCHEM LABORATORIES (TIANJIN) CO., LTD; ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD; TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD; ASYMCHEM LABORATORIES (FUXIN) CO., LTD; JILIN ASYMCHEM LABORATORIES CO., LTD; HONG, Hao; JAMES, Gage; LI, Jiuyuan; LI, Changfeng; HUANG, Gaochao; (16 pag.)US2018/148430; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 930-62-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 930-62-1 as follows.

A mixture of 2,4-dimethyl-lH-imidazole (5.00 g, 52.0 mmol),1 ,2-difluoro-4~nitrobenzene (8.27 g, 52.0 mmol), and sodium bicarbonate (4.37 g, 52.0 mmol) in DMSO (100 mL) was heated at 80 0C for 24 h . The reaction mixture was allowed to cool to rt and was poured into water (800 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic extracts were sequentially washed with water (500 mL) and brine solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The dark residue was dissolved in ethyl acetate (200 mL). Hexane (50 mL) was added to the solution. The resulting mixture was allowed to age for 72 h at it. The resulting solid was collected by vacuum filtration. The solid was dried under high vacuum to afford l-(2-fluoro-4-nitrophenyl)-2,4-dimethyl-lH-imidazole (6.68 g, 27.8 mmol., 54 % yield) as a yellow crystalline solid. LC-MS (M+H)+ = 236.1. IH NMR (500 MHz, CHLOROFORM-d) B ppm 8.13 – 8.22 (m, 2 H), 7.51 (dd, J=8.9, 7.3 Hz, 1 H), 6.72 (s, 1 H), 2.28 – 2.36 (m, 3 H), 2.22 – 2.28 (m, 3 H).

According to the analysis of related databases, 930-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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. name: Methyl 1H-imidazole-5-carboxylate

b) 3-(2,2-Dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 2,2-dimethyl-indan-1-ol (3.5 g, 21.6 mmol) in THF (160 mL) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 4.1 g, 32.3 mmol), and triphenylphosphine (9.09 g, 34.5 mmol). The reaction is cooled to 0 0C and diisopropyl azodicarboxylate (6.67 mL, 34.5 mmol) is added. After one hour the reaction 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-(2,2- dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester. HRMS: (ESI) m/z 271.1440 [(M+H)+ Calcd for C16H19N2O2: 271.1447]; 1H NMR (400 MHz, CDCI3) delta ppm 2.60 – 3.08 (m, 2 H), 3.92 (s, 3 H), 6.25 (s, 1 H), 7.03 (s, 1 H), 7.15 – 7.46 (m, 4 H), 7.80 (d, J=1.0 Hz, 1 H). The HCI salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1 N HCI in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCI salt of 3-(2,2-dimethyl-indan-1- yl)-3H-imidazole-4-carboxylic acid methyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17325-26-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 51605-32-4

N-Amination of ethyl 5-methyl-3H-imidazole-4-carboxylic acid (5.39 g, 34.96 mmol) following the general procedure. Purification by flash chromatography on silica gel eluting with 0% increasing to 4% methanol in dichloromethane gave a yellow-white solid (4.23 g, 71%). Rf 0.53 (7% MeOH in DCM), 1H NMR (300 MHz, CDCl3): delta 7.48 (s, 1H), 5.33 (s, 2H), 4.27 (q, J=6.9 Hz, 2H), 2.35 (s, 3H), 1.31 (t, J=6.9 Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 61.9 (CO2Et), 146.6, 140.4 (CH), 118.4, 60.8, 16.4, 14.7. MS, m/z (%) 170 (100) [M++1] Anal. Calcd for C7H11N3O2 (169.18): C, 49.70; H, 6.55; N, 24.84. Found: C 49.85, H 6.45, N 24.74.

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heim-Riether, Alexander; Rotella, David Paul; US2006/264624; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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 77 4-(6-Chloro-2,3-dihydro-indol-1-yl)-7-(2-imidazol-1-yl-ethoxy)-6-methoxy-quinazoline bis(methanesulfonate) salt This product was produced in 50% yield from 4-(6-chloro-2,3-dihydro-indol-1-yl)-6-methoxy-quinazolin-7-ol and N-(2-hydroxyethyl)imidazole (1.1 eq.) in a manner analogous to that described for Example 76. (M.P. 162-168 C. (dec); LC-MS: 422 (MH+); anal. RP18-HPLC RT: 3.94 min.).

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

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
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. 41806-40-0, name is 1-Methylimidazole-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methylimidazole-5-carboxylic Acid

Oxalyl chloride (1.1 equiv, 1.1 mL) and 1-methyl-1H-imidazole-5-carboxylic acid 10bb-1 (0.2 g, 1.6 mmol) are added to dry acetonitrile (2.6 mL) in a flame-dried flask under nitrogen atmosphere. N,N-dimethylformamide (2 drops) is added to the mixture. The reaction stirred at room temperature for 4 h. A large volume of diethyl ether is added to precipitate the product and the precipitated product is collected. The solid collected (10bb-2) is used in the next step without further purification.

According to the analysis of related databases, 41806-40-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gladius Pharmaceuticals, Inc.; SUTTON, Larry D.; ZAMBONI, Robert; BUREAU, Patrick; HASSANPOUR, Avid; MAMANI LAPARRA, Laura; VIDAL, Marc; WOO, Simon; ZHOU, Nancy; KEENAN, Richard M.; (127 pag.)US2019/100534; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C11H12N2O3, 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. Recommanded Product: Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

To 80.0 grams (0.363 moles) of methyl 2-ethoxybenzimidazole-7-carboxylate were added 400 ml of methanol, 99 grams of potassium carbonateand 94 grams of 4-bromomethyl-2′-cyanobiphenyl, and the resulting mixture wasstirred at ambient temperature for 24 hours. The reaction mass was quenchedwith chilled 2400 ml of water, filtered and washed with 160ml of water. The wetsolid was washed with 370 ml of hot ethyl acetate, and then dried at 50-60°C toget 105.0 grams of methyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate, substantially free from methyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-4-carboxylate.;150 g of 2-ethoxy-3H-benzoimidazole-4-carboxylic acid methyl ester, 750 ml.of methanol, 231.8 g of 4′-Bromomethyl-biphenyl-2-carbonitrile and 235.2 g ofpotassium carbonate were charged in a four neck round bottom flask equippedwith a half moon shaped Teflon type blade. The reaction mixture was heated toabout 50-55°C and was maintained under stirring for about 3-4 hours. Cooled thereaction mixture to about 25-35°C. Charged 6 liters of water in a four neck roundflask followed by cooling to about 0-5°C.The reaction mass was added to thewater under stirring over about 10-30 minutes under stirring and was stirredfurther for about 1-2 hours. Separated solid was filtered and washed with 300 ml.of water. The wet compound was charged in a four neck round bottom flask followed by charging 2250 ml of ethyl acetate. Reaction suspension was heated toabout 70-75°C and was stirred for about 30-45 minutes. Reaction suspension wascooled to about 0-5°C and was stirred for about 1-2 hours. Separated solid wasfiltered and washed with 150 ml of ethyl acetate. Solid obtained was dried at about60-65°C for about 3-5 hours to yield 177 g of title compound of Formula (V);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150058-27-8, its application will become more common.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2006/15134; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem