Month: March 2021

Related Products of 53316-51-1,Some common heterocyclic compound, 53316-51-1, name is 4,5-Dimethyl-1H-imidazole hydrochloride, molecular formula is C5H9ClN2, 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 4,5-dimethyl-1H-imidazole hydrochloride (2.0 g, 15.08 mmol) in DMF (20 mL) was added NaH (60 wt %, 908 mg, 22.63 mmol) in portions at 0 C. under N2. The resulting mixture was stirred for 0.5 h at 0 C. under N2, To the above mixture was added SEM-Cl (3.77 g, 22.63 mmol) dropwise at 0 C. The resulting mixture was stirred for additional 1 h. The reaction was quenched with water (50 mL) at 0 C., then extracted with EtOAc (100 mL¡Á2), washed with brine (50 mL¡Á2), dried and concentrated. The crude residue was purified by reverse phase C18 column chromatography (MeCN/H2O) to give the desired compound (5.12 g, 81.1%) as a yellow oil. ESI-MS m/z 227.10 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dimethyl-1H-imidazole hydrochloride, its application will become more common.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Yu, Jianming; Negretti-Emmanuelli, Solymar; Kim, In Jong; Or, Yat Sun; (89 pag.)US2019/315766; (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. 1467-16-9, name is 1H-Imidazole hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Imidazole hydrochloride

EXAMPLE 12 N-Cyano-N’-[2-(4-imidazolylmethoxy)ethyl]-N”-methylguanidine A stirred suspension of 4-(2-chloroethoxymethyl(imidazole hydrochloride (14.7 g.) and sodium azide (9.8 g.) in dry dimethylformamide (103 ml.) was maintained at 95 for 5 hours and then set aside overnight at room temperature. Following dilution with water and filtration, the filtrate was concentrated and the residue purified by chromatography on a dry column of alumina using ethanol. The product was basified with potassium carbonate (6.5 g.) in water (3 ml.) and the anhydrous residue was extracted with isopropyl alcohol (3 * 50 ml.). Concentration of the extracts afforded 4-(2-azidoethoxymethyl)imidazole (7.2 g.).

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; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33543-78-1, These common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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.

Reference example 1 2-hydrazinocarbonylimidazole 2-ethoxycarbonylimidazole was prepared according to the method given in the literature, J. Org. Chem., Vol.43, No.22, 4381 Kenneth L. kirk. 80percent hydrazine hydrate (4.6g, 75mmol) was added dropwise to a solution of 2-ethoxycarbonylimidazole (2.1g, 15mmol) in ethanol (20ml) at room temperature and stirring was continued for 2 h. The precipitate was filtered, washed with water and dried to give the title compound (1.7g, 90.0percent).

Statistics shows that Ethyl 1H-imidazole-2-carboxylate is playing an increasingly important role. we look forward to future research findings about 33543-78-1.

Reference:
Patent; Wakamoto Pharmaceutical Co., Ltd.; EP713876; (1996); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3584-66-5, name is 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole, 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. Formula: C8H4Cl4N2

To a suspension [OF 5-CHLORO-2-TRICHLOROMETHYL-1H-BENZOIMIDAZOLE] (100 mg, 0.37 mmol) in acetonitrile (4 mL) was added N-methylpiperazine (0.04 mL, 0.4 [MMOL).] The mixture was stirred for 10 min then ammonium acetate (29 mg, 0.38 [MMOL)] was added. After 18 h the reaction mixture was diluted with satd aq [NAHCO3] (10 mL), and then extracted with [DICHLOROMETHANE] [(3 X 10] mL). The combined extracts were dried [(NA2SO4)] and then concentrated under reduced pressure. The crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/dichloromethane) to afford 23 mg (22%) of the title compound. MS [(ESI)] : mass calculated for [C13H16N40,] 277.11 ; [M/Z] found, 278.2 [M+H] [+. 1H] NMR (400 MHz, CD30D) : 7.79-7. 74 [(M,] 2H), 7.45 (dd, [J =] 8.6, 2.0 Hz, [1H),] 4.23-4. 17 (m, 4H), 3.63-3. 58 (m, 4H), 3.01 (s, 3H).

The synthetic route of 3584-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/22060; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 28890-99-5, 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(3-bromophenyl)(9,9-dimethyl-9H-xanthen-4-yl)diphenylsilane (2, 300 mg, 0.55 mmol), 5H-benzo [d]benzo[4,5]imidazo[1,2-a]imidazole (3, 125 mg, 0.603 mg),cBRIDP (19.3 mg. 0.055 mmol) and tBuONa (132 mg, 1.37mmol) were dissolved in xylene (5 mL). The mixture wasdegassed by bubbling nitrogen through for 15 min. Alkylpalladiumchloride dimer (6 mg, 0.016 mmol) was added,and the mixture was again degassed by bubbling nitrogenthrough for another 15 min before being heated to 120 C.for 2 h. The reaction was quenched with water. The organicphase was separated and the aqueous phase was extractedwith dichloromethane. The combined organics was dried onMgS04 , filtered, and concentrated in vacuo. The crudeproduct was purified using reverse phase chromatography(20:80 to 70:30 THF:water, 1CV, 70:30 to 100:0 THF:water,10 CV, then THF). The crude product was then re-purifiedusing reverse phase chromatography (20:80 to 40:60 THF:water, 1 CV, 40:60 to 70:30 THF:water, 10 CV, then 70:30THF:water). The product was purified using normal phaseflash colunm chromatography (silica, 1:99 to 100:0 dichloromethane:heptane ). It was retained on the silica before 1:1THF:dichloromethane was used. This material was purifiedagain by normal phase chromatography (silica, 50:50 to100:0 dichloromethane:heptane) to afford Compound A aswhite solid.

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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universal Display Corporation; Wolohan, Peter; Feldman, Jerald; (128 pag.)US2018/287079; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6, A common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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 B8 a) A microwave vessel was charged with intermediate 15 (1 g, 4.63 mmol), l-[3- (trifluoromethyl)phenyl] -propane- 1,2-dione (1 g, 4.63 mmol), NH4(OAc) (3.57 g, 46.3 mmol) and AcOH (10 ml). The r.m. was stirred and heated at 160 0C for 7 min. under microwave irradiation. The r.m. was cooled and poured into a sat. aq. Na2Ctheta3 sol. The mixture was extracted with DCM. The o.l. was washed with H2O and dried (MgStheta4). Filtration and concentration under reduced pressure gave the crude product which was purified by flash chromatography over silicagel (eluent, 100: 0 to 90: 10 DCM/MeOH, gradient elution). The product fractions were collected and evaporated. The residue was purified further by preparative SFC (Chiralpak Diacel AD 20 mm, mobile phase:isocratic 80 % CO2, 20 % MeOH with 0.2 % isopropylamine). The product fractions were collected and worked up to yield 463 mg of compound 12 after trituration with DIPE (24 %).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1122-28-7, 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. 1122-28-7, name is 4,5-Dicyanoimidazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 34 16-(4,5-Bis(5-tetrazolyl)imidazol-1 -yl)hexadecanoic acidA mixture of 16-bromohexadecanoic acid methyl ester (3.50 g, 10.02 mmol), 4,5- dicyanoimidazole (1.52 g, 12.87 mmol), MeCN (30 ml), and K2CO3 (1.95 g, 14.1 mmol) was stirred at 80 0C for 66 h. Water (100 ml) and 1 N HCI (40 ml) were added, and the product was extracted twice with AcOEt. The combined extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. Recrystallization from MeOH (10 ml) yielded 3.41 g (88%) of 16-(4,5-dicyanoimidazol-1 -yl)hexadecanoic acid methyl ester as a colorless solid.

The chemical industry reduces the impact on the environment during synthesis 4,5-Dicyanoimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVO NORDISK A/S; WO2006/5667; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 39070-14-9 as follows. Safety of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

General procedure: To a solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (6) (1 eq.) in freshly distilled anhydrous THF (10?mL for 3?mmol of alcohol 6) was added dropwise lithium bis(trimethylsilyl)amide (1?M in THF, 1.1 eq.) at -78?C under an inert atmosphere. The reaction mixture was stirred around 5?min?at -78?C, and a solution of bis(2-chloroethyl)phosphoramidic dichloride (8) (1.1 eq.) in THF (3.3?mmol in 10?mL), previously cooled at -78?C, was added all at once at the same temperature (T0). The reaction mixture was stirred for 15-80?min, before the addition of a solution of the appropriate amine 18-22 (2-2.2 eq.) in THF (3?mL for 5?mmol of amine) and stirring was maintained at -78?C for 5?min to 75?min. These reaction times were determined by 31P NMR monitoring for each compound. The reaction was stopped by addition of water (20?mL for 3?mmol of alcohol 6), concentrated in vacuum and then extracted with EtOAc (3?*?50?mL for 3?mmol of alcohol 6). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using an eluent gradient (EtOAc/EtOH with TEA or NH4OH) to afford compounds 23-27 as yellow to orange oils.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-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 33468-67-6, Quality Control of 2-Methyl-4-(trifluoromethyl)-1H-imidazole

Compound 16.3. 2-Methyl-lH-imidazole-4-carbonitrile. Into a 100-mL round- bottom flask, was placed a solution of 2-methyl-4-(trifluoromethyl)- lH-imidazole (compound 16.2, 300 mg, 2.00 mmol) in 5% ammonium hydroxide (35 mL). The resulting solution was stirred for 4 days at room temperature, then the pH of the solution was adjusted to 7 with acetic acid. The aqueous phase was extracted with of ethyl acetate (3 x 10 mL) and the combined organic layers were dried ( a2S04), filtered, and concentrated under reduced pressur ompound as a light yellow solid.

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, 2-Methyl-4-(trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem