Month: October 2020

144689-93-0, Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 144689-93-0.

A mixture of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (5.0 g), potassium carbonate (5.75 g), and toluene (50 mL) is stirred at 45-500C for 45 minutes. N-(triphenylmethyl)-5-[4′-(bromomethyl)biphenyl-2- yl]tetrazole (13.2 g) and tetrabutylammonium bromide (1.3 g) are added and the mixture is stirred at 60-70 0C for 10 hours. The insoluble material is removed by filtration and the filtrate is washed with water (2*50 mL) at 60-700C. The filtrate is distilled under vacuum to produce a syrup. Methanol (25 mL) is added to the residue and stirred for 15 minutes at 25-35C. The mass is cooled to 0-5 0C and stirred at that temperature for 45 minutes. The precipitated solid is collected by filtration, washed with methanol (10 mL), and dried at 50-600C for 6 hours (yield 13.3 g).

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, Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below.

Synthesis of Ethyl 1~((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2- carboxylate (lnt~1a) ciInMa2-(Trimethylsilyl)ethoxymethyi chloride (12.8 g, 0.077 mol) was added to a stirred solution of ethyl imidazole-2-carboxylate (9.0 g, 0.064 mol) and potassium carbonate (17.7 g, 0.128 mol) in NtN-dimethylformamide (50 mL) at 0 ¡ãC. The mixture was allowed to stir from 0 ¡ãC to r.t. overnight. Water and ethyl acetate were added and the layers were separated. The separated aqueous layer was extracted with ethyl acetate (X2). The combined organic layers were washed with water (X2). The separated organic layer was dried (MgS04) and filtered. The solvents were removed in vacuo andchromatographic purification (ethyl acetate – hexane) of the residue gave imidazole InMa (12 g, 70percent) as a colorless oil. LCMS m/e (M + H+) – 271.1.

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:
Patent; SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang; WO2011/149874; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

492-98-8, These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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.

Synthetic example 7: yl)pyridin-2-amine)7A mixture of 1H,17-/-2,2′-biimidazole (840 mg, 6.3 mmol), A/-(4-bromophenyl)-A/- (pyridin-2-yl)pyridin-2-amine (6.59 g, 20.3 mmol) and Cs2C03 (10.14 g, 31.2 mmol) in DMF (70 mL) was degassed (N2 bubbling, 15 min). Cu20 (360 mg, 2.5 mmol) was added and the mixture was heated (140 “C, 72h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H20 and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc/CH2CI2/MeOH 35:60:5 then 32:60:8 then 28:60:12) to give Lambda/,Lambda ¡¤(4,4′-(1Eta, 1 “H^’-biimidazoie-l , 1 ‘-diyl)bis(4, 1 -phenylene))bis(A/-(pyridin- 2-yl)pyridin-2-amine) (1.36 g, 35%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/EtOAc/petrol) and then by distillation (sublimation apparatus 260 C, 10~6 mBar): m.p. 218 – 222 C (DSC); ‘H NMR (CDCI3l 400 MHz) delta 6.75 – 6.80 (m, 4H), 6.90 (ddd, J 0.8, 4.9, 7.3 Hz, 4H), 6.93 – 7.00 (m, 8H), 7.09 (d, J 1.0 Hz, 2H), 7.26 (s, 2H), 7.52 (ddd, J 2.0, 7.3, 8.3 Hz, 4H), 8.24 (ddd, J 0.7, 1.9, 4.9 Hz, 4H); 13C NMR (CDCI3, 100 MHz) delta 117.0, 118.6, 121.1 , 125.2, 127.5, 130.0, 133.7, 137.6, 144.3, 148.6, 157.7; HRMS (El) m/z 623.2420 C38H27 10 [M – H]+’ requires 623.2415.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 492-98-8.

Reference:
Patent; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; MACDONALD, James Matthew; BOWN, Mark; UENO, Kazunori; WEBER, Karl Peter; O’CONNELL, Jenny Lee; HIRAI, Tadahiko; WO2012/51666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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 2-(3 ,4-dimethoxyphenyl)-3 -i sopropyl -5 -(piperidin-4-yl)- 1 H-indole, HC1 (25 mg, 0.060 mmol) in DCM (0.5 mL) was neutralized by adding triethylamine drop wise (checked by pH paper). The solution was added to a vial containing i-methyliH-imidazole-5-carbaldehyde (9.95 mg, 0.090 mmol), acetic acid (0.01 ml, 0.175 mmol) at room temperature. The mixture was stirred at room temperature for 16 h. Sodium triacetoxyborohydride (19.15 mg, 0.090 mmol) was added to the reaction mixture and the mixture was stirred for another 6 h at room temperature. The reaction mixture was purified by reverse phase prep LCMS to provide 2-(3,4-dimethoxyphenyl)-3-isopropyl-5-(1 -((1 -methyl- 1H-imidazol-5-yl)methyl)piperidin-4-yl)- 1H-indole (1.27 mg, 4.34% yield,97.2% purity) as a pale solid. LC retention time = 1.734 mm [E]. MS (E) m/z: 473.2 (M+H).

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; HAQUE, Tasir S.; POSS, Michael A.; LOMBARDO, Louis J.; MACOR, John E.; PASUNOORI, Laxman; KUMAR, Sreekantha Ratna; (296 pag.)WO2018/26620; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, A common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 mixture of 10 (1.03 g, 10.7 mmol) and TrCl (3.29 g, 11.8 mmol, 1.1 eq) in MeCN (45 mL) was added Et3N (2.5 mL, 18.0 mmol, 1.7 eq) at rt. After stirring for 2 h, hexane (3 mL) and H2O (40 mL) were added and the mixture was filtered. The resultant cake was washed with water three times and dried in a house vacuumoven at 50 C to afford 18 (3.42 g, 95%) as a white powder.1H NMR (500 MHz, CDCl3) delta 7.10-7.13 (m, 5H), 7.35-7.38 (m, 10H), 7.53 (d, J = 1.1 Hz, 1H), 7.61 (d, J =1.7 Hz, 1H), 9.88 (s, 1H)

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

Reference:
Article; Yamashita, Megumi; Shimizu, Keita; Koizumi, Yasuaki; Wakimoto, Toshiyuki; Hamashima, Yoshitaka; Asakawa, Tomohiro; Inai, Makoto; Kan, Toshiyuki; Synlett; vol. 27; 19; (2016); p. 2734 – 2736;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1849-01-0, The chemical industry reduces the impact on the environment during synthesis 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, I believe this compound will play a more active role in future production and life.

General procedure: One equivalent of appropriate heterocyclic derivative was dissolved in DMF. Three equivalents of potassium carbonate and 1.2 equivalent of the appropriate 3-chloropropan-1-amine derivative were added. The resulting mixture was heated at 70C until disappearance of the starting material. The reaction was monitored by TLC. After 24-96 h, the solvent was removed under reduced pressure, and water added to the residue. The crude product was extracted with dichloromethane. The combined organic fractions were washed with water and dried over magnesium sulphate. Purification by thick layer chromatography or column chromatography was performed.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-benzo[d]imidazol-2(3H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, A common compound: 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

:[0172]A suspension of aminoguanidinium nitrate (150 mg, 1.09 mmol) and K2CO3(150 mg, 1.09 mmol) in N, N-dimethylformamide (DMF) (3 mL) was stirred at room temperature for 1 h. A solution of 1H-benzo [d] imidazole-2-carboxylic acid (162 mg, 1.0mmol) in N, N-dimethylformamide (DMF) (5 mL) was treated with N, N’-carbonyldiimidazole (CDI) (180 mg, 1.1 mmol) at 0. The solution was stirred at room temperature for 1 h. Then it was added to the suspension. The resulting mixture was stirred at room temperature for 3 h , then it was heated to 100 for 3 h. The mixture was cooled to room temperature, filtered and concentrated to give crude 3- (1H-benzo [d] imidazol-2-yl) -1H-1, 2, 4-triazol-5-amine (Intermediate 1) as white solid (290mg, 40purity) which was used in next step directly. Mass spectrum (ESI) m/z calc. for C9H8N6[M+H]+201.08, found 201.20.

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-Benzimidazole-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; HUANG, Niu; QI, Xiangbing; WANG, Yanli; SUN, Yuze; (56 pag.)WO2017/152842; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below.

Toluene (180 L) is placed into a reactor and water (3.17 L) is added, followed by addition of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (18.0 Kg). The mass is stirred for about 10 minutes, heated to about 45C, and potassium carbonate (25.85 Kg) is added. The temperature of the mass is raised to about 65C and maintained for about 45 minutes. N-(triphenylmethyl)- 5-[4′-(bromomethyl)biphenyl-2-yl]tetrazole (48.9 Kg) and tetrabutylammonium bromide (4.82 Kg) are added at the same temperature and the mixture is stirred at 60-700C for 10 hours. Reaction completion is verified using thin layerchromatography (TLC). After the reaction is complete, the mass is washed with water (3*120 L) at about 500C. The mass is cooled to about 25C and toluene (468 L) and potassium tertiary-butoxide (12.6 Kg) is added, then the mass is maintained at the same temperature for about 1 hour. Water (0.85 L) is added and the mass is maintained at the same temperature for about 2 hours. Reaction completion is verified using TLC, then 5-methyl-2-oxo-(1 ,3-dioxolene-4-yl)methyl chloride (20 Kg), tetrabutylammonium bromide (4.82 Kg), and sodium carbonate (3.96 Kg) are added at 40-450C. The mass is stirred at about 55C for about 11 hours. After the reaction is complete, the mass is cooled to about 20C, water (540 L) is added and the pH is adjusted to about 6-7 by adding 10% aqueous HCI. The layers are separated. The aqueous layer is extracted with toluene (240 L). The organic layers are combined and washed with water (270 L). The solvent is distilled under reduced pressure. Acetone (189 L) is added to the residue and the mixture is heated to about 45C to produce a solution, then the solution is cooled to about 300C and maintained for about 20 minutes, followed by cooling to about 2C and maintaining for about 3 hours. The formed solid is filtered, washed with acetone (54 L), and dried for about 4 hours. The material obtained is re- crystallized from acetonitrile to yield 34.0 Kg of the title compound.

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; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below.

l-Beiuothiazol-6->l-imidazolidm-2-one lL-_84b: 15Umg, 0.6849mmol) was reacted with 5>br¡ãnkappa>-. -methyl- U l-imidazole (12l.3mg, O.753mmol).1.4’diox?nie (SmL). copper iodide ( 12.99mg, 0.0684mmol). trans N.N’-diim’th^l-cyclohexane- 1 ,2-diamine (2l>.176mg.0.20Smiotanol) and potassium phosphate (435.0 ling, 2.05mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOl ) in CIlCI.? ) afforded 85mg of the product (4l.o4% >ield).1I I NMR (300 MH/. CDCh): o 8.9 (?, HIV 8.35 (d.1 M).8. l(d. III).7.7 (dd. III). 7.5-7.4(brs, IH),7.0(brs, HH.4.1 (t, 211), 3.9 (t.211), 3.6 (s.311).I CMS: 100%,inV 299.8 (M+ 1)HPLC: 98.52%

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; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2010/149755; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 98873-55-3

A 10 mL schienk tube was charged with powdered KOH (116 mg, 2.07 mmol), DMSO (1 mL), purged with Argon and cooled at 18CC with a water bath. A solution of 2-imidazol-1- ylacetonitrile (104 mg, 0.97 mmol) and CS2 (117 pL, 1.9408 mmol) in DMSO (500 pL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 30 minutes. Then a solution of freshly prepared (2-bromo-5-fluoro-indan-1-yl)methanesulfonate (step 3) in DMSO is added dropwise. After 30 minutes stirring at room temperature, the reaction is poured into H20 (20 mL). The aqueous phase is extracted with AcOEt (3 x 5 mL), the combined organic phases were washed with H20 (10 mL), brine (10 mL), dried with Mg504, filtered and evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes/ethylacetate 2:1-1:3) afford2-(6-fluoro-4,8b-dihydro-3aH-indeno[1 ,2-d][1 ,3]dithiol-2-ylidene)-2-imidazol-1 -yl-acetonitrile as an inseparable (2:1) mixture of E/Z-isomers.

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, 98873-55-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien, Daniel; BONVALOT, Damien; JEANMART, Stephane, Andre, Marie; WO2015/11194; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem