Month: May 2021

Synthetic Route of 68282-52-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 68282-52-0 name is 2,4-Dimethyl-1H-imidazole-5-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

94a) 2-(2-(1-benzyl-4-piperidinyl)ethyl)-5,7-dimethyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one To a solution of 2-(1-benzyl-4-piperidinyl)ethanamine (2.2 g), 2,5-dimethylimidazole-4-carbaldehyde (1.2 g) and acetic acid (0.3 ml) in 1,2-dichloroethane (25 ml) was added sodium triacetoxyborohydride (8.1 g) under ice-cooling. The reaction mixture was mixed at room temperature for 2 days, and then the reaction solution was washed with an aqueous potassium carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was dissolved in THF (50 ml). To the reaction solution were added N,N’-carbonyldiimidazole (1.6 g) and DBU (1.6 ml), and mixed at room temperature for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform. The reaction mixture was then washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate/methanol = 10/1). The product was recrystallized from ethyl acetate-hexane to obtain the title compound as colorless powder (1.3 g, 32%). NMR (CDCl3) delta:1.26-1.35 (2H, m), 1.53-1.59 (2H, m), 1.67-1.74 (2H, m), 1.88-1.97 (1H, m), 1.97 (2H, t, J=10.5), 2.15 (3H, s), 2.56 (3H, s), 2.84-2.90 (2H, m), 3.44-3.49 (2H, m), 3.48 (2H, s), 4.21 (2H, s), 7.20-7.30 (5H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dimethyl-1H-imidazole-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1695961; (2006); A1;,
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 914306-50-6 as follows. Computed Properties of C21H24N2

Synthesis of (OC-6-22)-bis{5-(9H-carbazol-9-yl)-2-[1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl-kappaN3]phenyl-kappaC}{2-[1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl-kappaN3]phenyl-kappaC}iridium(III) (abbreviation: [fac-Ir(iPrCzpim)2(iPrpim)]) (0430) First, 1.8 g (0.8 mmol) of [Ir(iPrCzpim)2Cl]2 and 150 mL of dichloromethane were put into a 200-mL three-neck flask. A solution obtained by dissolving 0.6 g (2.3 mmol) of silver trifluoromethanesulfonate in 62 mL of methanol in a dark place was put in a dropping funnel attached to the 200-mL three-neck flask in a dark place. This methanol solution of silver trifluoromethanesulfonate was added dropwise into the reaction solution, and stirring was performed at room temperature for 26 hours. After reaction for the predetermined time, the reaction solution was filtered through Celite and the solvent of the resulting filtrate was distilled off to give an ocher solid. Then, all of the obtained ocher solid, 0.94 g (3.1 mmol) of 1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole (abbreviation: HiPrpim), 15 mL of methanol, and 15 mL of ethanol were put in a 200-mL three-neck flask, and the mixture was refluxed for 36 hours. After reaction for the predetermined time, the solvent of the reaction solution was distilled off to give a yellow solid. A solution obtained by dissolving this yellow solid in tetrahydrofuran (THF) was filtered through a filter aid in which Celite, neutral silica, and Celite were stacked in this order, so that a yellow solution was obtained. The solvent in this yellow solution was distilled off to give a yellow solid. This yellow solid was purified by silica gel column chromatography. Toluene was used as a developing solvent. The solvent of the resulting fraction was distilled off, so that a yellow oily substance was obtained. This yellow oily substance was recrystallized with ethyl acetate and hexane to give a yellow solid. Purification by a train sublimation method was performed on this yellow solid, so that 240 mg (0.17 mmol) of a yellow solid was obtained in a yield of 11%. The synthesis scheme is shown in (c-1). (0431) Protons (1H) of the yellow solid obtained as described above were measured by nuclear magnetic resonance (NMR). The obtained values are shown below. The 1H-NMR chart is shown in FIG. 32. The results revealed that [fac-Ir(iPrCzpim)2(iPrpim)], which is the organometallic complex represented by Structural Formula (600), was obtained in Synthesis Example 2. (0432) 1H-NMR. delta (CD2Cl2): 0.57 (d, 3H), 0.70 (d, 3H), 0.92 (m, 18H), 1.14 (d, 3H), 1.19 (dd, 6H), 1.24 (d, 3H), 2.27 (m, 1H), 2.34 (m, 1H), 2.54 (m, 1H), 2.62 (m, 2H), 2.81 (m, 1H), 6.07 (d, 1H), 6.27 (t, 2H), 6.39 (d, 1H), 6.44 (dd, 1H), 6.52 (t, 1H), 6.67 (dd, 1H), 6.82 (d, 1H), 6.90 (m, 7H), 6.99 (m, 8H), 7.12 (d, 1H), 7.22 (d, 1H), 7.34 (m, 9H), 7.49 (m, 3H), 7.90 (d, 2H), 7.95 (m, 2H). (0433) Next, an ultraviolet-visible absorption spectrum (absorption spectrum) and an emission spectrum of a dichloromethane solution of [fac-Ir(iPrCzpim)2(iPrpim)] were measured. The measurement of the absorption spectrum was conducted at room temperature, for which an ultraviolet and visible spectrophotometer (V550 type manufactured by JASCO Corporation) was used and the dichloromethane solution (0.0100 mmol/L) was put in a quartz cell. In addition, the measurement of the emission spectrum was performed at room temperature in such a manner that an absolute PL quantum yield measurement system (C11347-01 manufactured by Hamamatsu Photonics K.K.) was used and the deoxidized dichloromethane solution (0.0100 mmol/L) was sealed in a quartz cell under a nitrogen atmosphere in a glove box (LABstar M13 (1250/780) manufactured by Bright Co., Ltd.). Measurement results of the obtained absorption and emission spectra are shown in FIG. 33, in which the horizontal axis represents wavelength and the vertical axes represent absorption intensity and emission intensity. Note that the absorption intensity is shown in FIG. 33 using the results obtained in such a way that the absorbance measured by putting only dichloromethane in a quartz cell was subtracted from the absorbance measured by putting the dichloromethane solution (0.0100 mmol/L) in a quartz cell. (0434) As shown in FIG. 33, the organometallic complex [fac-Ir(iPrCzpim)2(iPrpim)] has emission peaks at 479 nm and 514 nm, and blue-green light emission was observed from the dichloromethane solution. (0435) Next, [fac-Ir(iPrCzpim)2(iPrpim)] obtained in this example was analyzed by liquid chromatography-mass spectrometry (LC-MS). (0436) In the analysis by LC-MS, liquid chromatography (LC) separation was carried out with UltiMate 3000 produced by Thermo Fisher Scientific K.K., and the MS analysis was carried out with Q Exactive produced by Thermo Fisher Scientific K.K. (0437) In the LC separation, a given column was used at a column temperature of 40 C., and solution sending was performed in such a manner that an appropriate solvent was selected, the sample w…

According to the analysis of related databases, 914306-50-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; TSUNOI, Toshiaki; INOUE, Hideko; ISHISONE, Takahiro; WATABE, Takeyoshi; (129 pag.)US2017/213989; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 149520-94-5, name is Ethyl 2-amino-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 149520-94-5, HPLC of Formula: C6H9N3O2

a) Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylate Ethyl 2-amino-1H-imidazole-4-carboxylate (6.45 mmol, 1 g) and triethylamine (10.04 mmol, 1.016 g) were suspended in dry ACN (30 ml) and cooled to 0 C. Acryloyl chloride (9.67 mmol, 0.875 g) dissolved in dry ACN (4 ml) was added dropwise. The resulting mixture was slowly warmed to RT and subsequently heated to 50 C. for 16 h. The solvent was evaporated and the residue purified by flash chromatography. 0.358 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): delta 1.37 (t, 3H), 2.92 (t, 2H), 4.18 (t, 2H), 4.37 (q, 2H), 7.40 (s, 1H), 8.78 (bs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-amino-1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 380177-22-0, The chemical industry reduces the impact on the environment during synthesis 380177-22-0, name is (5-Chloro-1-methyl-1H-benzo[d]imidazol-2-yl)methanol, I believe this compound will play a more active role in future production and life.

A solution of (5-CHLORO-1-METHYL-1H-BENZIMIDAZOL-2-YL) METHANOL (1.5 g, 7.7 mmol) dissolved in CH2CI2 at room temperature was treated with Dess-Martin periodinane (4.9 g, 11.5 mmol). The reaction was stirred for 15 hours before the solvent was removed. The residue was purified by flash column chromatography (0-3% MeOH in CH2CI2) to give the product (1.0 g, 66% YIELD). 1H NMR (300 MHz, CDCI3) 6 : 4.16 (s, 3 H), 7.40-7. 47 (m, 2 H), 7.90-7. 93 (m, 1 H), 10.11 (s, 1 H).

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-Chloro-1-methyl-1H-benzo[d]imidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 60713-78-2, A common heterocyclic compound, 60713-78-2, name is 5-Chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H4ClN3O3, 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 5-chloro-6-nitro-1 ,3- dihydro-benzoimidazol-2-one (5.63 g, 26.35 mmol) was added phosphorus oxychloride (35 ml_) and the reaction mixture was heated to 85 0C for 36 h. The reaction mixture was concentrated and the residue triturated with cold saturated aqueous sodium bicarbonate (to pH 8, 0.8 L). The resulting precipitate was collected and dried to yield the titled compound (5.43 g, 89% yield). MS (ESI/CI): mass calcd. for C7H3CI2N3O2, 231.0; m/z found, 232.0 [M+H]+. Step C: 2,6-Dichloro-1 -(2-methoxy-ethoxymethyl)-5-nitro-1 /-/-benzoimidazole.

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; JANSSEN PHARMACEUTICA NV; WO2009/134750; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

53525-60-3, name is Ethyl 1-trityl-1H-imidazole-4-carboxylate, 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. Quality Control of Ethyl 1-trityl-1H-imidazole-4-carboxylate

To a stirred solution of compound LXIX (3 g; 8.87 mmol) and ethyl 1-trityl-1H-imidazole-4- carboxylate (XLV; 10 g; 26.62 mmol) in THF (50 ml) was added sodium bis(trimethylsilyl)amide (44 ml, 1 .OM in THF, 44.35 mmol) dropwise at 0C. Upon complete addition, the resultant solution was stirred at ambient temperature for 2 h. The reaction mixturewas diluted with a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine solution and dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to obtain 4-(tert-butyl)-N-(5-chloro-6-(2-oxo-2-(1- trityl- 1 H-imidazol-4-yl)ethyl)pyridin-2-yl)benzenesulfonamide LXXV, as a keto-enol tautomeric mixture. MS (M+1): 675.12. The crude material was carried forward to next stepwithout purification.

The synthetic route of 53525-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORGINE B.V.; BAKTHAVATCHALAM, Rajagopal; BASU, Manas Kumar; BEHERA, Ajit Kumar; VENKATESHAPPA, Chandregowda; HEWSON, Christopher Alexander; KADNUR, Sanjay Venkatachalapathi; KALINDJIAN, Sarkis Barret; KULKARNI, Bheemashankar; SAXENA, Rohit; SURESH, Juluri; VISWANATHAN, Vellarkad; ZAINUDDIN, Mohd; DHARSHINIS, Akila Parvathy; KRISTAM, Rajenda; WO2015/97122; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 19485-38-2, name is 1-Methylimidazole-4,5-dicarboxylic Acid, 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 19485-38-2, category: imidazoles-derivatives

In a 100 mL round bottom flask was added 1 mmol4,5-dicarboxy-1-methyl-1H-imidazole,1 mmol HOBT, dissolved in 20 mL ethyl acetate and stirred at 0 C for 30 min. Join 1mmol DCC, 0 reaction 2.5h, magnetic stirring.Dropping 1mmol dehydroabiety amine ethyl acetate solution 5mL,Reaction overnight. TLC followed the reaction until the reaction was complete. Then ice bath for half an hour, making DCU precipitation. DCU was removed by filtration and the filtrate was diluted to 200 mL and washed with 5% NaHCO3 (10 mL * 3), 10% citric acid (10 mL * 3) 2-3 times and saturated brine (10 mL * 3). The ethyl acetate layer was dried over anhydrous sodium sulfate. Filtration, the filtrate point plate, two points, the two points separated by the column to give compound L1 and compound L2, respectively, characterized.The L1 yield was 34.7% and the L2 yield was 35.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylimidazole-4,5-dicarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Forestry University; Xu Li; Zhao Fengyi; Lu Wen; Xu Yuanyuan; Wang Luna; Xue Huayu; Cao Fuliang; (9 pag.)CN106220570; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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.

Intermediate 23; 2-Chloro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyridor2,3-dlpyrimidin-4-amine1 -Methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 167 mg, 1.72 mmol), 2,4- dichloropyrido[2,3-d]pyrimidine (500 mg, 2.50 mmol) were suspended in ethanol (10 mL) and TEA (0.24mL, 1.72 mmol) was added. The reaction mixture was heated at 700C overnight and the title product was obtained after filtration (421mg).1H NMR (300 MHz, DMSO-d6) delta ppm 11.33 (s, 1 H) 9.16 (d, 1 H) 9.01 (s, 1 H) 7.54-7.72(m, 3H) 3.75 (s, 3 H). 103496-1PLCMS: 261 [M+H]4

The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); 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. 16931-35-4, name is 7-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16931-35-4

General procedure: To a solution of aryl halide (1.0 equivalence) and boronic acid (1.1 equivalence) in 1,4-Dioxane (1.0 M), was added potassium carbonate (2.0 equivalence, 2.0 M aqueous solution) followed by palladium catalyst [1,1?-bis(diphenylphoshphino)ferrocene]-dichloropalladium (II) 1:1 complex with dichloromethane (0.10 equivalence). The reaction mixture was degassed for 5 minutes by bubbling nitrogen gas directly into the solution using syringe needle. The reaction vessel was closed tightly and stirred at 100 oC for overnight or until the completion of reaction as judged by TLC. The reaction mixture was filtered through a pad of silica/celite to remove the catalyst, poured into water (25 mL) and extracted with ethyl acetate (3 x 25 mL), the organic layer was washed with water (20 mL), dried over Na2SO4 and concentrated and purified by chromatography.

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; Kashyap, Sudhir; Sandler, Joel; Peters, Ulf; Martinez, Eduardo J.; Kapoor, Tarun M.; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2253 – 2260;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10394-39-5, These common heterocyclic compound, 10394-39-5, name is 5-Methoxy-1-methyl-1H-benzo[d]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.

To a solution of 198 5-methoxy-1-methyl-1H-benzo[d]imidazole (500 mg, 3.08 mmol) in 200 CH2Cl2 (6 ml) was added 201 BBr3 (3.1 g, 12.33 mmol) dropwise at 0 C. After addition, the mixture was stirred for 2 h at 0 C. The mixture was then quenched by slow addition to 202 ice water (50 mL). The resulting mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the 203 title compound (100 mg, 21.9%) as a white solid which was used in next step without further purification. LCMS (m/z): 149.1 (M+1).

The synthetic route of 10394-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Duncan, Kenneth W.; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Munchhof, Michael John; Jin, Lei; (118 pag.)US2019/83482; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem