Category: imidazoles-derivatives

Application of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 soluiton of 1H-imidazole-4-carbonitrile (300 mg, 3.2 mmol) in THF (50 mL) was added LiA1H4 (365 mg, 9.6 mmol). After stirred at reflux overnight, the reaction mixture was quenched by H20 (2 mL). And the mixture was dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated in vacuum. The residue was used for next step without further purification.

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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; Preparation of olmesartan medoxomilTo dimethyl acetamide (300 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (50 gms) and powdered sodium hydroxide (26 gms). To this, 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (135 gms) was charged at 45-500C. The contents were stirred for 5 hours at 45-500C. Diisopropylethyl amine (100 ml) was charged to the reaction mass at 40-450C. A solution of 5-methyl-2-oxo-1 , 3-dioxane-4-yl)methyl chloride (80 gms) diluted with dimethyl acetamide (160 ml) was slowly added to the reaction mass at 40-450C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganic impurities, charcoalized using charcoal (10 gms) andstirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (100 ml) slowly at 25-30C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-5C and filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500ml), neutralized with base and extracted in dichloromethane (500 ml). The clear dichloromethane extract was then concentrated under reduced pressure and stripped off with acetone. The residue thus obtained was isolated from acetone (250 ml) to give 55 gms of the title compound. Chromatographic purity- > 99%

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., COA of Formula: C4H5ClN2O2S

General procedure: The amino phenyl derivative (0.4 mmol, 1 equiv) was dissolvedin pyridine absolute (3 mL) and was spiked with sulfonyl chloride/acid chloride (1.5 equiv). The reaction mixture was stirred overnightat rt (refluxed in case of amide coupling). The reaction wasquenched by adding 10 mL of 2 N HCl and extracted with ethylacetate (3 50 mL). The organic layers werewashed with saturatedNaHCO3 (50 mL) and brine (50 mL), dried over magnesium sulfate,filtered and concentrated to dryness. The product was purified byCC. The title compound was prepared by reaction of (5-(3-aminophenyl)thiophene-2-yl)(2,6-difluoro-3-hydroxyphenyl)methanone (30)(100 mg, 0.30 mmol) and 1-methyl-1H-imidazole-4-sulfonyl chloride (81 mg, 0.45mmol) according to Method C. The product was purified by CC (dichloromethane/methanol95:5); yield: 72% (103 mg). 1H NMR (500 MHz, acetone-d6)delta 9.17 (s, 1H), 9.01 (s, 1H), 7.75-7.72 (m, 2H), 7.64-7.61 (m, 2H), 7.54 (d, J= 4.1 Hz, 1H), 7.50-7.43 (m, 1H),7.39-7.34 (m, 2H), 7.21 (td, J= 9.4, 5.5 Hz, 1H), 7.04 (td, J= 8.8, 1.9Hz, 1H), 3.76 (s, 3H);13C NMR (125 MHz, acetone-d6) delta 180.7, 155.1, 153.6,151.6, 149.5, 147.5, 143.3, 142.7, 140.7, 140.1, 138.3, 134.5, 130.9, 126.2,122.5, 121.9, 120.4, 118.4, 112.6, 112.4, 34.2; MS (ESI): 476.21 (M+H)+)+; HPLC purity ? 98% (Rt = 12.54 min).

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; Abdelsamie, Ahmed S.; Bey, Emmanuel; Gargano, Emanuele M.; Van Koppen, Chris J.; Empting, Martin; Frotscher, Martin; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 56 – 68;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2,Some common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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 1. 4-Iodo-l-methyl-lH-imidazole and 5-iodo-l-methyl-lH-imidazole (1205) [00394] Under an atmosphere of nitrogen at 0 C, a solution of 4-iodo-lH-imidazole (5.82 g, 30.00 mmol) in THF (50 mL) was treated with portionwise addition of sodium hydride (60% dispersion in mineral oil, 1.44 g, 36.00 mmol). After stirring for 30 min at 0 C, iodomethane was added (2.8 mL, 45.00 mmol) and the mixture was stirred for 1 h at 0 C. The reaction mixture was poured into water (100 mL) and was extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 6.24 g (90%) of a -3 : 1 mixture of 4-iodo-l-methyl-lH-imidazole and 5- iodo-1 -methyl- lH-imidazole as a light yellow solid. MS (ESI) m/z 209 [M+H]+. Step 2. terf-Butyl 4-(l-methyl-lH-imidazol-4-yl)-3,6-dihydropyridine-l(2H)-carboxylate and terf-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6-dihydropyridine-l(2H)-carboxylate (1207) [00395] A -3 : 1 mixture of 4-iodo-l -methyl- lH-imidazole and 5-iodo-l-methyl-lH-imidazole (6.24 g, 30.00 mmol), fert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5,6- dihydropyridine-l(2H)-carboxylate (1 1.1 g, 36.00 mmol), Pd(dppf)Cl2 CH2Cl2 (2.45 g, 3.00 mmol) and sodium carbonate (6.36 g, 60.00 mmol) in water (60 mL) and 1,4-dioxane (300 mL) was stirred under an atmosphere of nitrogen for 3 h at 80 C. After cooling to ambient temperature, the reaction mixture was poured into EtOAc (100 mL) and was washed with water (2 x 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (eluting with a gradient of 1-5% DCM/MeOH) to afford 5 g (57%) of a -3 : 1 mixture of tert-butyl 4-(l-methyl-lH-imidazol-4-yl)- 3,6-dihydropyridine-l(2H)-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6- dihydropyridine-l(2H)-carboxylate as a yellow oil. MS (ESI) m/z 264 [M+H]+. Step 3. tert-But l 4-(l-methyl-lH-imidazol-4-yl)piperidine-l-carboxylate and tert-butyl 4-(l- methyl-lH-imidazol-5-yl)piperidine-l-carboxylate (1209) [00396] A -3 : 1 mixture of tert-butyl 4-(l-methyl-lH-imidazol-4-yl)-3,6-dihydropyridine- l(2H)-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6-dihydropyridine-l(2H)- carboxylate (5 g, 19.01 mmol) and palladium on carbon (10 wt. %, 5 g) in MeOH (100 mL) was evacuated and backfilled with hydrogen several times and was then charged with hydrogen. The resulting mixture was stirred for 1 h at ambient temperature before being filtered and concentrated under vacuum, resulting in 1.7 g (34%) of a -3 : 1 mixture of tert-butyl 4-(l-methyl- lH-imidazol-4-yl)piperidine-l-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5- yl)piperidine-l-carboxylate as a yellow oil. MS (ESI) m/z 266 [M+H]+.

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

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); 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. 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, A new synthetic method of this compound is introduced below., Recommanded Product: 939-70-8

General procedure: To a solution of 2-acetylbenzimidazole 3 (0.800 g, 5.00 mmol) in ethanol (50 mL) were added 60% aqueous potassium hydroxide (15 mL) and 4-fluorobenzaldehyde (0.620 g, 5 mmol) at 0 C with stirring. The reaction mixture was stirred at room temperature until complete consumption of starting material (monitored by TLC, petroleum ether/chloroform, 1/3, V/V). The crushed ice and diluted hydrochloric acid solution were added for total precipitation of the yellow solid (0.846 g), which were obtained by vacuum filtration and then recrystallized in ethanol.

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; Liu, Han-Bo; Gao, Wei-Wei; Tangadanchu, Vijai Kumar Reddy; Zhou, Cheng-He; Geng, Rong-Xia; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 66 – 84;,
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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, A new synthetic method of this compound is introduced below., Recommanded Product: 60-56-0

2-Mercapto-l-methylimidazole (84 mg, 0.73 mmol) was added neat to a solution of 2- bromo-l-[l-(4-chloro-phenyl)-cyclopropyl]-ethanone (200.5 mg, 0.73 mmol) in CH3CN (5 mL) at room temperature, then Et3N (0.203 mL, 1.46 mmol) was added neat to the mixture and the reaction was stirred over night. The reaction was then quenched by addition of a small spatula of resin 2-chlorotrityl chloride, stirred for IH then the mixture was filtered and concentrated under vacuum. The crude mixture was purified by flash chromatography (hexane/EtOAc gradient 0-50%) to afford the title compound (216.5 mg, 97%) as cream-yellow solid. TLC single spot at R/ 0.13 (hexane/EtOAc 7:3); Mp = [95.5- 97.0 0C]; 1H NMR (270 MHz, CDCl3): delta 1.19 (q, J = 3.7 Hz, 2H), 1.63 (q, J = 3.2 Hz, 2H), 3.62 (s, 3H), 3.86 (s, 2H), 6.87 (d, J = 1.2 Hz, IH), 6.98 (d, J = 1.2 Hz, IH), 7.32 (d, J = 0.7 Hz, 4H); LC/MS (APCI) m/z 307 (M++H); HPLC tr = 1.88 min (100%) in 10% water-acetonitrile.

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

Synthetic Route of 2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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 500 mL four-neck round-bottomed flask (RBF) equipped with an overhead stirrer, a nitrogen inlet, a 125 mL addition funnel, and a thermocouple was purged with anhydrous nitrogen for 10 min. The flask was charged with 2- (4-bromophenyl) -1-phenyl-1 H-benzo [d] imidazole (25.0 g, 71.59 mmol) and THF (250.0 mL) , and then cooled to -71? of internal temperature. 1.6 M n-butyl lithium solution (67.0 mL, 107.2 mmol) in hexane was added dropwise into the flask via an addition funnel for 30 min, and the mixture was further stirred at an internal temperature of -72oC of for 30 min. 2-Isopropoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (32.0 mL, 171.99 mmol) was added to the resulting dark red solution via an addition funnel for 30 min while maintaining the temperature of below -70oC. After removing a cooling bath, the brown slurry was warmed to room temperature and stirred for 16 hrs. The reactants were concentrated by using a rotary evaporator, dissolved in dichloromethane (350.0 mL) , and washed with water (200.0 mL) to obtain a cloudy mixture. The aqueous layer was extracted with dichloromethane (2 X 150.0 mL) , and the combined organic layers were dried with MgSO4, filtered, and concentrated by using a rotary evaporator. The resulting yellow solid was washed with hexane (100.0 mL) and tan colored solids (22.2 g) were obtained by mostly removing the color. The solids were divided into two crops and recrystallized from acetonitrile (? 180.0 mL per crop) to obtain pale orange crystalline solids as a title compound (16.5 g, 41.6 mmol, 58percent) .

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; CHO, Sang Hee; NA, Hong Yeop; TANG, Zhengming; FENG, Shaoguang; MOON, Doo-Hyeon; (43 pag.)WO2017/156698; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9, 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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step F Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in dry DMF (250 ml) at ambient temperature was added Et3 N (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step.

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, 4-Imidazolemethanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5817678; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 7098-07-9, A common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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.

In a 100 mL three-necked flask, TMEDA (2.86 g, 3.72 ml, 24.7 mmol, Eq: 2.37) was combined with pentane (10 ml) to give a colorless solution. N-BuLi 1.6M in hexane (15.6 ml, 25.0 mmol, Eq: 2.4), followed by 1-ethyl-1H-imidazole (1 g, 10.4 mmol, Eq: 1.00) were added dropwise at -25° C. for 30 min. The reaction mixture was stirred at RT for 1 h (light yellow suspension). Afterwards, the suspension was cooled to -65° C. and THF anhydrous (30 ml) was added (-65° C. to -48° C.). A solution of iodine (3.83 g, 15.1 mmol, Eq: 1.45) in THF anhydrous (20 ml) was added dropwise to the reaction mixture (internal temperature remained below -55° C.)=>brown suspension. Stirring was continued as the reaction was gradually warmed to 0° C. during 1.3 hours (brown milky solution). Eventually, the reaction was quenched by adding 4 mL of methanol. Work up: The reaction mixture was poured into 50 mL sat. Na2SO3 and extracted with EtOAc (2*100 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated i. V. Purification: The crude material was purified by flash chromatography (silica gel, 50 g, 20percent to 100percent EtOAc in heptane) to provide in the more polar fractions 417 mg of the desired title compound as yellow oil. MS (ESI): 222.9 [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; HOFFMANN-LA ROCHE INC.; Aebi, Johannes; Amrein, Kurt; Hornsperger, Benoit; Kuhn, Bernd; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; US2014/128429; (2014); 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 1H-Benzimidazole-7-carboxylic acid

Example 144 : N-(5-((5-(4-(dimethylcarbamoyl)phenyl)pyridin-2-yl)amino)pyridin-3- yl)-1H-benzo[d]imidazole-4-carboxamide. [0711] To a mixture of 4-(6-((5-aminopyridin-3-yl)amino)pyridin-3-yl)-N,N- dimethylbenzamide (80 mg, 0.24 mmol) in pyridine (2 mL) was added lH-benzo[d]imidazole-4-carboxybc acid (58 mg, 0.36 mmol) and EDOHC1 (92 mg, 0.48 mmol), the reaction mixture was stirred at 50 C for 2 h to give a brown suspension. LCMS (Rt = 0.660 min; MS Calc’d: 477.2; MS Found: 478.1 [M+H]+). The mixture was concentrated under reduced pressure to give a residue. The residue was purified by washing with MeOH (5 mL) to give a crude product. Then further purified by prep-HPLC (0.225% FA as an additive) to give N-(5-((5-(4- (dimethylcarbamoyl)phenyl)pyridin-2-yl)amino)pyridin-3-yl)-1H-benzo[d]imidazole-4- carboxamide (7.9 mg, yield: 7%) as a white solid. LCMS (Agilent LCMS 1200-6140 A, mobile phase: from 99% [water + 0.1% FA] and 1% [MeCN + 0.1% FA] to 95% [water + 0.1% FA] and 5% [MeCN + 0.1% FA] in 0.6 min, then changed to 100% [MeCN + 0.1% FA] under this condition for 3.4 min, finally back to 99% [water + 0.1% FA] and 1 % [MeCN + 0.1% FA] and under this condition for 0.5 min.) purity is 97.48%, Rt = 2.126 min; MS Calc’d: 477.2; MS Found: 478.3 [M+H]+. NMR (400 MHz, DMSO-rie) d 2.91-3.05 (6H, m), 7.04 (1H, d, J = 8.8 Hz), 7.45-7.53 (3H, m), 7.76 (2H, d, J = 8.4 Hz), 7.85-7.94 (1H, m), 8.00-8.07 (2H, m), 8.61-8.72 (3H, m), 8.74-8.80 (1H, m), 8.83-8.92 (1H, m), 9.75 (1H, br s).

The synthetic route of 46006-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETRA PHARMA CORPORATION; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; KESICKI, Edward A.; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (450 pag.)WO2019/126731; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem