Tag: M.W=100-200

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. 857070-66-7, name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol

A mixture of b-3 (0.069 mol) and N-propylamino-morpholine (0.207 mol) was stirred at 125C for 4 hours, and then taken up in CH2C12/CH3OH. The organic layer was washed with a 10% solution OfK2CO3 in water, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (37 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 90/10/0.5; 20-45mum). The pure fractions were collected and the solvent was evaporated, yielding 16.5g of intermediate b-4 (82%).

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; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5465-29-2, These common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, 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 50 ml of water, 450 ml of concentrated sulfuric acid (i.e., 90% concentration) was added dropwise, 50.0 g of 2-propylbenzimidazole was added, and 300 ml of a 30% aqueous solution of hydrogen peroxide was added dropwise. The reaction was exothermic to reflux and the dropping speed was maintained to keep the reaction solution boiling.After completion, the reaction was continued for 3 hours.Add water 400ml, cold to room temperature.The solid was precipitated and stirred at 0-5 C for 3 hours, filtered, washed with water, washed with 100% of 5% sodium sulfite aqueous solution and dried to constant weight to give 2-propylimidazole-4,5-dicarboxylic acid as a white solid (21.7 g, 35%), HPLC purity 89.4%,

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huanggang LUBAN Pharmaceutical Co.,Ltd. (LUBAN); YANG, XIAOLONG; LIU, XIANGQUN; LI, QIANG; CHEN, QIAN; YANG, TIEBO; (17 pag.)CN104262260; (2016); B;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-1-methyl-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

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:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-38-6, The chemical industry reduces the impact on the environment during synthesis 3034-38-6, name is 5-Nitro-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-nitro-1H- imidazole (260 mg, 2.299 mmol) in DMF (5 mL) was added 1.0 M NaHMDS/THF (2.53 mL, 2.53 mmol) dropwise at rt. After stirring at rt for 20 min, 1-bromopropan-2-one (315 mg, 2.299 mmol) was added very slowly. The mixture was stirred at rt for ON. Water was added and extracted with EtOAc (4 x 50 mL). The organic layer was concentrated. The residue was purified via silica gel chromatography (12g, DCM-10%MeOH) to give 1-(4-nitro-1H-imidazol-1-yl)propan-2-one (180 mg, 1.064 mmol, 46 % yield). (2333) MS ESI m/z 170.0 (M+H)+ (2334) 1H NMR (499 MHz, CD3OD) delta 8.06 – 8.04 (m, 1H), 7.66 – 7.62 (m, 1H), 5.17 – 5.12 (m, 1H), 2.28 (s, 3H).

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-Nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); A1;,
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. 93-84-5, name is 5-Nitro-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Nitro-1H-benzo[d]imidazol-2(3H)-one

Intermediate 301 was prepared from 5-nitro-1,3-dihydro-2H-benzo[d]imidazol-2-one 10 (CAS: 984-5) and bromoacetamide (CAS: 683-57-8) by the method indicated in the scheme below:

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 93-84-5.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1003-21-0, 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 1003-21-0 as follows.

lntermediate 1: step b (1-Methyl-lH-imidazol-5-yl)(tetrahydro-2H-pyran-4-yl)methanone A clear colorless solution of 5-bromo-l-methyl-lH-imidazole (1.12 g, 6.93 mmol) in THF (10 mL) was placed in an ice bath and ethylmagnesium bromide (3.0 M in Et20, 2.31 mL, 6.93 mmol) was added via syringe. The reaction mixture was stirred for 20 minutes at room temperature. N-Methoxy~N-methyltetrahydro-2H~pyran-4~ca.rboxamide (1.0 g, 5.8 mmol. Intermediate 1 : step a. Procedure A) was added neat by syringe (using 1 mL THF rinse to quantitate transfer), and the resulting white suspension was stirred at room temperature for 2 days. The mixture was diluted with saturated aqueous NH4C1 followed by water, then was extracted with EtOAc (3 x). The organic phase was dried (Na2S04), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography two times (1 -4% MeOH-DCM first column; 40-60% CH CN-DCM second column) to provide the title compound as a white crystalline solid.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, Adding some certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0.

To 10 mL of Acetonitrile were added 3 mmol (1.05 g) of methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate (WO 2012/018635) 3.3 mmol (376 mg) of 2-mercapto-1-methylimidazole and 6.6 mmol (910 mg) of K2C03. The solution was stirred at room temperature overnight. When TLC showed no remaining methyl 4-chloro-3-[(E)- dimethylaminomethyleneamino]sulfonyl-5-nitro-benzoate the reaction mixture was diluted with 10 mL of water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried with Na2S04 and evaporated under reduced pressure. The crude product was then purified by recrystallization from ethanol to yield 1.04 g of yellow crystals (81 % yield). 1H NMR (200 MHz, DMSO-cf6) d 8.66 (d, J = 1.9 Hz, 1 H), d 8.34 (d, J = 1.8 Hz, 2H), d 7.28 (s, 1 H), d 6.87 (s, 1 H), d 3.91 (s, 3H), 3.51 (s, 3H), d 3.10 (s, 3H), d 2.92 (s, 3H). MS m/z: not found

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 60-56-0.

Reference:
Patent; UNIVERSITAeT WIEN; ERKER, Thomas; SCHREPPEL, Philipp; (235 pag.)WO2019/193159; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 670-96-2, name is 2-Phenyl-1H-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 670-96-2, Safety of 2-Phenyl-1H-imidazole

General procedure: A mixture of Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand II (21.6 mg, 0.020 mmol), and F-PEG (0.25 g, 0.10 mmol) in MeOH (1 mL) was heated to dissolve all the reagents added completely and MeOH was removed under the reduced pressure. H2O (6 mL) was added to the residue and then 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol) and imidazole (2a, 13.6 mg, 0.20 mmol) were added. The whole reaction mixture was stirred under an O2 atmosphere at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL×3). The organic layer was washed with H2O (10 mL×3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (26.4 mg, 78%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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. Recommanded Product: (1H-Benzo[d]imidazol-2-yl)methanamine

(R/5)-2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)- l,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-V, 20 mg, 0.046 mmol), (1H- benzo[d]imidazol-2-yl)methanamine (10.24 mg, 0.070 mmol), HATU (22.92 mg, 0.060 mmol), and 4-methylmorpholine (18.76 mg, 0.185 mmol) were added to DMF (1 mL). This was stirred for 1 h before it was purified via preparative LCMS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge CI 8, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 methanohwater with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanol: water with 10-mM ammonium acetate; Gradient: 45-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give (R/5)-N- ((lH-benzo[d]imidazol-2-yl)methyl)-2-hydroxy-2-(4-(5-(3-phenyl-4- (trifluoromethyl)isoxazol-5-yl)-l,2,4-oxadiazol-3-yl)phenyl)acetamide (12.8 mg, 0.023 mmol, 49.3 % yield): LCMS = 561.1 [M+H]+; ‘H NMR (400 MHz, methanol- cU) 5 ppm 8.19 (2 H, d, J=8.58 Hz), 7.51-7.79 (10 H, m), 7.34 (2 H, dd, J=6.05, 3.19 Hz), 5.27 (1 H, s), 4.76-4.94 (2 H, m); HPLC peak RT = 2.6 min (Method E).

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; ZHANG, Yanlei; WO2011/133734; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-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 51605-32-4, HPLC of Formula: C7H10N2O2

[2757] To a stirred solution of 964 (Ethyl 4-methyl-5-imidazole carboxylate, 7.7 g, 50 mmol) in 100 ml of acetone at room temperature, was added K2CO3 (6.9 g, 50 mmol) portionwise. Stirred at room temperature for 25 minutes, added in MeI (5 ml, 80 mmol) stirred for 21/2 h, (monitored reaction by TLC). Additional K2CO3 (3.09 g, 22 mmol) and MeI (3 ml) were added. Stirred reaction for 16 h, then filtered reaction mixture and rinsed with acetone (80 ml). A clear filtrate obtained. Filtrate was evaporated and the residue was chromatographed (eluent methylene chloride/methanol (60:1) to afford 1.8 g of solid. This solid was purified by Prep Plate chromatography ((20:1) CH2Cl2:MeOH NH3), compound still impure. Another column chromatography ((50:1) CH2Cl2:MeOH.NH3) was done to afford 383 mg of the desired product, compound 965.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-methyl-1H-imidazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Schering Corporation; US2004/122018; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem