Month: September 2021

Reference of 17289-26-8, These common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, 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 1-methyl-1H-imidazole-4-carboxaldehyde (0.71 g, 6.45 mmol) in THF (60 mL) was treated with acetic acid (738 jiL, 12.90 mmol) and dimethylamine (2 M in THF, 6.45 mL, 12.90 mmol) and stirred for 2 h. Sodium triacetoxyborohydride (2.74 g,12.90 mmol) was added and the mixture stirred overnight. The reaction was diluted with EtOAc and poured into saturated aqueous NaHCO3. The aqueous phase was concentrated in vacuo and the resultant residue suspended in MeOH-DCM. This was filtered and the filtrate concentrated in vacuo. The crude product was purified using an SCX-2 cartridge and the relevant eluent was concentrated in vacuo to give a residue which was furtherpurified by chromatography eluting from 0-10% (2M NH3 in MeOH) in DCM to afford the title compound as an amber oil (340 mg).?H NMR (300 MHz, DMSO): oe 7.44 (1H, s), 6.91 (1H, s), 3.60 (3H, s), 3.24 (2H, s), 2.11(6H, s).

Statistics shows that 1-Methyl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 17289-26-8.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; SUTTON, Jonathan Mark; CAPALDI, Carmelida; ARMANI, Elisabetta; WO2015/91281; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68892-07-9, name is Methyl 2-mercapto-1-methyl-1H-imidazole-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 68892-07-9, category: imidazoles-derivatives

428 g (2.49 mol) of the commercially available compound (XXIII) were stirred in 2.81 of 3 M aqueous sodium hydroxide solution at 15 C. for 30 mm. Using 6hydrochloride acid, the pH was then adjusted to 1-2 and the precipitate was filtered off with suction. Drying gave 363of the compound (XXIV). 1H-NMR (400 MHz, CD3OD): oe=3.82 (s, 3H),7.58 (s, 1H)

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, Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, REINER; HEIL, MARKUS; JANSEN, JOHANNES-RUDOLF; KUEBBELER, SUSANNE; WILCKE, DAVID; KOEHLER, ADELINE; WILLOT, MATTHIEU; EILMUS, SASCHA; ILG, KERSTIN; MALSAM, OLGA; LOESEL, PETER; PORTZ, DANIELA; ANDERSCH, WOLFRAM; (92 pag.)US2018/7900; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 88a: (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanol To a flask containing 5-bromo-l -methyl- lH-imidazole (650 mg, 4.04 mmol) was added THF (10 mL) and the clear homogeneous solution was stirred at room temperature as z’PrMgCl (2 M in diethylether, 2 mL, 4 mmol) was added. A whitish suspension resulted. The suspension was stirred at room temperature for 30 minutes, then a solution of 4-chloro-2-methoxy-3-(4- (trifluoiOmefhyl)benzyr)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (660 mg, 1.36 mmol, Intermediate 81 : step b) in THF (5 mL) containing LaCl3-LiCl complex (0.5 M solution THF, 5 mL, 2.5 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight at 35 C. After 14 hours, the reaction mixture was quenched with saturated aqueous NH4C1 solution. The aqueous portion was extracted with EtOAc (3 x 40 mL) and the combined organics were washed with brine and dried over MgS04. The brine portion was back-extracted with DCM (3 x 40 mL) and dried over MgS04. The organics were filtered and concentrated to dryness to afford a tan oil. The residue was purified by FCC (2% MeOH-DCM increasing to 10% MeOH) to provide the title compound as an off white solid.lH NMR (500 MHz, CDCI3) delta 8.13 (d, J = 2.0 Hz, 1H), 7.76 (d, J = 8.7 Hz, 1H), 7.50 (d, J = 8.2 Hz, 2H), 7.44 – 7.35 (m, 4H), 7.31 (d, J= 1 1.4 Hz, 1H), 7.05 (d, J= 8.0 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 6.19 (s, 1H), 4.67 (s, 1H), 4.32 (s, 2H), 4.07 (s, 3H), 3.46 (s, 3H), 2.52 (s, 3H), 2.45 – 2.33 (m, 3H); MS (ESI): mass calcd. Chemical Formula: C30H2CIF3N4O?, Exact Mass: 566.2, m/z found 567.1 [M+H]”.(4~Chk>ro~2~niethoxy~3-(4-(irifluQmethyl- lH-im.idazol-5-yl)methanol was purified by chiral SFC (Stationary phase: CHIRALPAK AD-H 5 muetaiota 250 x 20 mm, Mobile phase: 75% C02, 25% EtOH), to give two enantiomers. The first eluting enantiomer was Example 88b and the second eluting enantiomer was Example 88c.

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

1-hydroxybenzotriazole monohydrate (16 mg, 0.118 mmol), 3- (ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine (Hydrochloric Acid (1)) (35 mg, 0.183 mmol), and 1-methyl-1H-imidazole-4-carboxylic acid (15 mg, 0.119 mmol) were combined in DMF (0.2 mL) under nitrogen at room temperature and allowed to stir for 40 min. 4-(7-morpholinoquinazolin-5-yl)oxycyclohexanamine (25 mg, 0.0761 mmol) was added, and stirring was continued a further 30 min. Saturated sodium bicarbonate was added, an the mixture was extracted with EtOAc (2x). The combined organics were washed with water (2x), brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography over 4g silica gel using a 0-10% methanol / DCM gradient to yield 1- methyl-N-((1s,4s)-4-((7-morpholinoquinazolin-5-yl)oxy)cyclohexyl)-1H-imidazole-4- carboxamide (6 mg, 17%). 1H NMR (400 MHz, CDCl3) delta 9.44 (s, 1H), 9.10 (s, 1H), 7.51 (d, J = 1.3 Hz, 1H), 7.40 – 7.34 (m, 1H), 7.09 (d, J = 8.4 Hz, 1H), 6.78 (d, J = 1.9 Hz, 1H), 6.57 (d, J = 2.0 Hz, 1H), 4.74 (d, J = 3.9 Hz, 1H), 4.11 (tq, J = 9.9, 6.2, 5.3 Hz, 1H), 3.89 (dd, J = 5.9, 3.9 Hz, 4H), 3.73 (s, 3H), 3.43 – 3.33 (m, 4H), 2.29 – 2.17 (m, 2H), 2.04 – 1.73 (m, 6H). ESI-MS m/z = 433.05 (M+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; VERTEX PHARMACEUTICALS INCORPORATED; MAXWELL, John, Patrick; JACKSON, Katrina, Lee; TANG, Qing; MORRIS, Mark, A.; RONKIN, Steven, M.; XU, Jinwang; COTTRELL, Kevin, M.; CHARIFSON, Paul, S.; (280 pag.)WO2019/143678; (2019); 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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below., Safety of 6-Aminobenzimidazole

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
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. 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 147403-65-4

Example 17Methyl 2-ethoxy- l -((2′-(5-oxo-4,5-dihydro-l ,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- l H- benzo[£/]imidazole-7-carboxylate of formula la Solid triphosgene (0.12 g, 0.4 mmol) was added to a mixture of methyl 2-ethoxy-l -((2′- ((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)-lH-benzo[i/]imidazole-7-carboxylate (of formula Va; 0.44 g, 1 mmol), THF (10 ml) and triethylamine (0.5 g, 5 mmol) and the mixture was stirred in a closed pressure flask at the temperature of 80 C for 8 hours. After cooling water (20 ml) was added under stirring and, after stirring for 30 minutes, the mixture was acidified with acetic acid. The separated honey-like product was extracted with ethyl acetate, the extract was dried and evaporated to dryness. 0.45 g of a product was obtained, which contained 65.5 % of the compound of formula la according to HPLC. Double crystallization from ethyl acetate yielded 0.28 g (59.5 %) of a product, which contained 95.2 % of the compound of formula la.

According to the analysis of related databases, 147403-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; WO2012/139536; (2012); 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Isopropyl-1H-imidazole

A mixture of 4-chloro-1-fluoro-2-nitrobenzene 1.01 g, 2-isopropylimidazole 634 mg, N,N-diisopropylethylamine, 1.46 mL and acetonitrile 12 mL was heated under reflux for 15 hours. The solvent was distilled off and water was added to the residue which was then rendred acidic with diluted hydrochloric acid. After washing the same with diethyl ether, the aqueous layer was rendered alkaline with aqueous sodium hydroxide solution and extracted twice with chloroform. The organic layer was washed with water, dried over magnesium sulfate, and removed of the solvent by distillation to provide 0.98 g of the title compound. 1H-NMR(CDCl3, delta): 1.22(6H, d, J=6.9Hz), 2.5-2.8(1H, m), 6.81(1H, d, J=1.2Hz), 7.09(1H, d, J=1.5Hz), 7.39(1H, d, J=8.5Hz), 7.71(1H, dd, J=2.3, 8.5Hz), 8.05(1H, d, J=2.7Hz). MS(m/z): 267(M++2), 265(M+).

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; ASKA Pharmaceutical Co., Ltd.; EP2103613; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 41806-40-0, name is 1-Methylimidazole-5-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. Computed Properties of C5H6N2O2

[2514] Take crude (881) from Step A, and dissolve in DMF (60 ml), and add NH(OMe)Me(3.14 g), DEC(6.14 g), HOBT(2.16 g), NMM(11 ml), and stir at room temperature over night. Add 1.0 N HCL until acetic (pH=2), wash with diethyl ether. Add, while stirring, K2CO3 until basic pH=8, saturate with NaCl, and extract with (4×).CH2Cl2. Dry with MgSO4, filter and evaporate to obtain product (882) (3.23 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41806-40-0, its application will become more common.

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

Synthetic Route of 33529-02-1, 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. 33529-02-1, name is 1-Decyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

1-Decylimidazole was synthesized according to previous literature. 1-Decylimidazole (5.49 g, 26.3 mmol) and 3-bromopropene (3.1 g, 26.3 mmol) were added to a 100 mL round-bottom flask containing 30 mL ethanol with condenser. The reaction mixture was stirred for 24 h. Solvent was then removed under reduced pressure. The crude product was washed three times with ether and dried in a vacuum oven at 50 C for 24 h to give the 1-allyl-3-decylimidazolium bromide (ADIm). 1-Allyl-3-decylimidazolium bromide: This compound was obtained in 97% as a yellow viscous oil. 1H NMR (DMSO-d6, 400 MHz): delta 9.30 (s, 1H, -N-CH-N-), 7.87 (s, 1H, -N-CH-CH-N-), 7.78 (s, 1H, -N-CH-CH-N-), 6.07 (m, 1H, -CH=CH2), 5.32 (dd, 2H, =CH2), 4.87 (d, 2H, -CH2-CH=CH2), 4.19 (t, 2H, -N-CH2-), 1.79 (m, 2H, -CH2-CH2-), 1.24 (broad, 14H, -CH2-CH3), 0.85 (t, 3H, -CH3).

The chemical industry reduces the impact on the environment during synthesis 1-Decyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhou, Chuan; Li, Yi-He; Jiang, Zhen-Hua; Ahn, Kwang-Duk; Hu, Tian-Jiao; Wang, Qing-Hua; Wang, Chun-Hua; Chinese Chemical Letters; vol. 27; 5; (2016); p. 685 – 688;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 162356-38-9, These common heterocyclic compound, 162356-38-9, name is 2-(2-Bromophenyl)-1H-imidazole, 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: First, 100 mmol 2-phenylimidazole derivative introduced 400 ml of triethylamine. And continuously added with stirring 200 ml alkynyl, 6 mmol triphenylphosphine, 6 mmol of copper iodide (I) and 3 mmol of palladium acetate (II). The reaction mixture was then stirred for 20 hours at 80 . After cooling, the reaction mixture was diluted with 400 ml of methylene chloride, to separate a solid via filtration through a bed of salt C The filtrate was evaporated to dryness. The residue was dissolved in 300 ml of methylene chloride, 100 ml of concentrated aqueous ammonia with individual cleaning solution three times, and then washed three times with 100 ml of water, and dried over magnesium sulfate. After the solvent was removed in vacuo, the crude product was adsorbed onto silica gel (5 grams per gram of crude product silicone), and loaded into a silica gel column. First with dichloromethane to remove byproducts, but will be converted to THF solvent to elute the product. With spherical fractionating tube distillation or sublimation, resulting in the manipulation of the vacuum pump oil / solids release low-boiling components.

The synthetic route of 162356-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; HEIL, HOLGER; JOOSTEN, DOMINIK; PFLUMM, CHRISTOF; GERHARD, ANJA; BREUNING, ESTHER; (214 pag.)TWI520958; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem