Month: May 2021

These common heterocyclic compound, 5098-11-3, name is 5-Amino-1H-imidazole-4-carbonitrile, 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. Formula: C4H4N4

Example 1 : General procedure for the preparation of cyano-imidazo[1 ,5- a]pyrimidines of general formula (I) following Scheme 1N-[3-(8-cyano-imidazo[1 ,5-a]pyrimidin-4-yl)-phenyl]-N-ethyl- ethanesulfonamide0.035 g (0.32 mmol) of delta-amino-I H-imidazole^-carbonitrile and 0.1 g (0.32 mmol) of N-[3-[3-(dimethylamino)-1 -oxo-2-propenyl]phenyl]-N-ethyl- ethanesulfonamide were dissolved in 10 ml of glacial acetic acid. After refluxing for 4 hours, the solvent was removed by reduced pressure distillation. To the resultant residue 10 ml of dichloromethane and 10 ml of a saturated solution of sodium bicarbonate were added. The two layers were separated, and the aqueous layer was washed with 10 ml of dichloromethane. The organic layers were washed with 10 ml of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate gave a yellow solid, 58 mg (yield 51%) of N-[3-(8-cyano-imidazo[1 ,5-a]pyrimidin-4-yl)-phenyl]-N-ethyl- ethanesulfonamide1H NMR (400 MHz, CDCI3): delta 1.2 (3H, t, J= 7.2 Hz), 1.41 (3H, t, J= 7.6 Hz), 3.08 (2H, q, J= 7.6 Hz), 3.84 (2H, q, J= 7.6 Hz), 6.85 (1 H, d, J= 4 Hz), 7.58- 7.71 (3H, m), 7.76-7.77 (1 H, m), 8.25 (1 H, s), 8.56 (1 H, d, J= 4 Hz). MS (ES) m/z = 356 (MH+) HPLC = 94.2%

The synthetic route of 5-Amino-1H-imidazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRER INTERNACIONAL, S. A.; WO2006/84835; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6232-92-4, name is 6-Nitro-1H-benzo[d]imidazol-2-amine, 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. COA of Formula: C7H6N4O2

VIII-1 7-nitropyrimido[1,2-a]benzimidazole hydrochloride and 8-nitropyrimido[1,2-a]benzimidazole hydrochloride (Compounds No. XXVI)A mixture of 2 g (11.2 mmol) of 2-amino-5-nitro-benzimidazole (J. Med. Chem., 1995, 38(20), 4098-4105) and of 3.6 ml (15 mmol) of 1,1,3,3-tetraethoxypropane in 50 ml of ethanol and 2 ml of concentrated hydrochloric acid is refluxed for 12 hours. 1.97 g of a beige precipitate is recovered by filtration and is dried under reduced pressure. A mixture of isomers is obtained, which is used as it is in the subsequent step.

The synthetic route of 6-Nitro-1H-benzo[d]imidazol-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2009/42873; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 887571-32-6, These common heterocyclic compound, 887571-32-6, name is N-Methyl-1-(5-methyl-1H-benzo[d]imidazol-2-yl)methanamine, 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: Approximately 0.5 mmol of 2 and 0.5 mmol of HATU were dispensed in 24 reaction wells (MiniBlock XT) using a dispensing spatula and funnel. To each well were added 10 mL of anhydrous MeCN, (0.5 mmol) of the appropriate amine in MeCN, and then 0.13 mL of DIPEA (0.75 mmol) through the septa sheet. The reaction block was covered and shaken at room temperature for 180 minutes (TLC monitored). Two grams of silica gel were added to each well and the reaction block was placed on a parallel centrifugal evaporator. After automated flash chromatography, the obtained pure intermediate (0.25 mmol) and 4 mL of formic acid (50%) were dispensed in 24 reaction wells (MiniBlock XT), heated to 70 C and shaken vigorously for 2 h whereupon TLC showed no remaining starting material. Silica gel (1 g) was added to each well and the mixture was evaporated, dried on a parallel centrifugal evaporator and the dry solid was chromatographed to give the desired product.

Statistics shows that N-Methyl-1-(5-methyl-1H-benzo[d]imidazol-2-yl)methanamine is playing an increasingly important role. we look forward to future research findings about 887571-32-6.

Reference:
Article; Moukha-Chafiq, Omar; Reynolds, Robert C.; Nucleosides, nucleotides and nucleic acids; vol. 33; 11; (2014); p. 709 – 729;,
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. 10394-39-5, name is 5-Methoxy-1-methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxy-1-methyl-1H-benzo[d]imidazole

To a solution of 5-methoxy-l-methyl-lH-benzo[d]imidazole (500 mg, 3.08 mmol) in CH2C12 (6 ml) was added BBr3 (3.1 g, 12.33 mmol) dropwise at 0C. After addition, the mixture was stirred for 2 h at 0C. The mixture was then quenched by slow addition to ice water (50 mL). The resulting mixture was extracted with CH2C12 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the 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+l).

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; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100730; (2014); 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. 177760-04-2, name is Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 177760-04-2

A solution of the amino ester (36.94 g, 0.218 mol) in 200 ml of acetic acid was added drop wise to a solution of sodium nitrite (100 g, 1.449 mol) and water (300 ml) cooled in an ice-water bath, and stirred. The temperature of the reaction mixture, which was measured to be around -5 – 1O0C was raised to rt and and the reaction mixture stirred overnight. The reaction mixture was extracted with DCM (3 x 150 mL). The combined DCM layers were dried and evaporated to yield a reddish residue which was separated by column chromatography on silica gel employing as eluent EA/hexane (30%) to yield 1-N- methyl-2-nitroimidazole-5-carboxylic acid ethyl ester (“nitro ester”) as a light brown solid (27 g, yield 62%).

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 177760-04-2.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2007/2931; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 914306-50-6, 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. 914306-50-6 name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, 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.

Step 3: Synthesis of (OC-6-21)-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(I II) (abbreviation: [mer-Ir(iPrCzpim)2(iPrpim)]) (0417) Into a 100-mL three-neck flask were put 2.8 g (2.3 mmol) of [Ir(iPrCzpim)2(acac)] (abbreviation) obtained in Step 2, 1 g (3.3 mmol) of 1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole (abbreviation: HiPrpim), and 20 mL of glycerol, and the mixture was heated and stirred at 150 C. for 12 hours. After reaction for the predetermined time, the reaction solution was filtered and a precipitate was washed with methanol to give a yellow solid. This yellow solid was recrystallized with tetrahydrofuran (THF) to give a yellow solid. The yield was 2.1 g (1.5 mmol) and 64%. Purification by a train sublimation method was performed on 1.0 g of this yellow solid, so that 790 mg (0.52 mmol) of a yellow solid was obtained. The synthesis scheme of Step 3 is shown in (b-3). (0418) Protons (1H) of the yellow solid obtained through Step 3 described above were measured by nuclear magnetic resonance (NMR). The obtained values are shown below. The 1H-NMR chart is shown in FIG. 29. The results revealed that [mer-Ir(iPrCzpim)2(iPrpim)], which is the organometallic complex represented by Structural Formula (600), was obtained in Synthesis Example 2. (0419) 1H-NMR. delta (CD2Cl2): 0.26 (dd, 6H), 0.32 (d, 6H), 1.00 (m, 18H), 1.13 (d, 3H), 1.26 (d, 3H), 2.10 (m, 2H), 2.23 (m, 1H), 2.38 (m, 2H), 2.86 (m, 1H), 6.25 (dd, 2H), 6.32 (d, 1H), 6.48 (d, 1H), 6.56 (m, 2H), 6.63 (dd, 1H), 6.69 (dd, 1H), 6.70 (d, 1H), 6.76 (d, 1H), 6.84 (m, 2H), 6.88 (d, 1H), 7.07 (d, 1H), 7.16 (m, 8H), 7.28 (m, 8H), 7.41 (m, 6H), 7.56 (t, 1), 8.06 (dd, 4H). (0420) Next, an ultraviolet-visible absorption spectrum (absorption spectrum) and an emission spectrum of a dichloromethane solution of [mer-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. 30, 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. 30 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. (0421) As shown in FIG. 30, the organometallic complex [mer-Ir(iPrCzpim)2(iPrpim)] has emission peaks at 481 nm and 515 nm, and blue-green light emission was observed from the dichloromethane solution. (0422) Next, [mer-Ir(iPrCzpim)2(iPrpim)] obtained in this example was analyzed by liquid chromatography-mass spectrometry (LC-MS). (0423) 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. (0424) 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 was prepared by dissolving [mer-Ir(iPrCzpim)2(iPrpim)] in an organic solvent at an arbitrary concentration, and the injection amount was 5.0 muL. (0425) A component with m/z of 1432.64, which is an ion derived from [mer-Ir(iPrCzpim)2(iPrpim)], was subjected to the MS2 analysis by a Targeted-MS2 method. For the Targeted-MS2 analysis, the mass range of a target ion was set to m/z=1432.64±2.0 (isolation window=4) and detection was performed in a positive mode. Measurement was performed with energy (normalized collision energy: NCE) for accelerating a target ion in a collision cell set to 30. The obtained MS spectrum is shown in FIG. 31. (0426) FIG. 31 shows that product ions of [mer-Ir(iPrCzpim)2(iPrpim)] are mainly detected around m/z=1129 and m/z=964. The results in FIG. 31 show characteristics derived from [mer-Ir(iPrCzpim)2(iPrpim)] and therefore can be regarded as important data for identifying [mer-Ir(iPrCzpim)2(iPrpim)] contained in a mixture. (0427) It is presumed that the product ion around m/z=1129 is a cation in a state where the ligand HiPrpim (abbreviation) is …

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, and friends who are interested can also refer to it.

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

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. 169770-25-6, name is Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Methyl-4-nitro-imidazole-2- carboxylate 40 (5 g, 27 mmol) was dissolved in 1 : 1 mixture of MeOH and EtOAc (150 mL). A slurry of moist 10% PdVC in EtOAc was added and the contents were stirred vigorously under hydrogen (70 psi) for 14 h. The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as green solid. The crude amine without any further purification was taken up in CH3CN (150 mL). Contents were cooled to 0 0C and DIEA (6.9 mL, 37.7 mmol) was added. A solution of 1- methyl-4-nitro-2-trichloroacetylpyrrole 23 (7.6 g, 28.2 mmol) in CH3CN (20 mL) was added and the reaction mixture was allowed to stir at ambient temperature for 14 h, EPO during which solid precipitated out. The reaction mixture was filtered to furnish 42 as yellow solid (5 g, 60%). The filtrate was concentrated and the residue was taken up in MeOH. Et2O was added to furnish a second crop of 42 (1 g, 12%). 1H-NMR (DMSO-d6) 611.14 (s, exch, IH, NH), 8.19 (d, IH, J = 1.2 Hz, Py-CH), 7.80 (d, IH, J = 1.2 Hz, Py-CH), 7.68 (s, IH, Im-CH), 3.96 (s, 3H, CH3), 3.94 (s, 3H, CH3), 3.82 (s, 3H, CH3). 13C-NMR (75 MHz, DMSO-d6) 6158.9 (+, s, CO), 157.4 (+, s, CO), 137.1 (+, s, Im-C2), 134.1 (+, s, Py-C4), 131.2 (+, s, Im-C2), 128.2 (-, d, Py-C5), 125.4 (+, s, Py-C2), 1 15.2 (-, d, Im-C5), 1 10.2 (-, d, Py-C3), 52.0 (-, q, OCH3), 37.9 (-, q, CH3), 35.2 (-, q, CH3). EI-HRMS: m/z calcd for Ci3Hi5N5O5 321.1073; found 321.1094 (M+, 20%), 279.0997 (100%), 194.0830 (72%), 153.0317 (35%).

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 169770-25-6.

Reference:
Patent; UNIVERSITY OF SASKATCHEWAN; WO2007/45096; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

19485-38-2, name is 1-Methylimidazole-4,5-dicarboxylic Acid, 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: 19485-38-2

Example 238 HATU (83 mg, 0.22 mmol) was added to a mixutre of l-methyl-lH-imidazole-4,5- dicarboxylic acid (17.8 mg, 0.10 mmol) and an HCl salt of Intermediate 32 (80 mg, 0.21 mmol) in DMF (1 mL) and DIPEA (0.091 mL, 0.52 mmol) and the reaction mixture was stirred at rt for 16 h. The reaction was filtered and purified by preparative HPLC to afford the title compound (10.5 mg). LC-MS retention time = 2.85 min; m/z = 827.2 [M+H]+. (Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0- 100% B over 3 minutes, then a 0.75-minute hold at 100% B; Flow: 1.0 mL/min;

The synthetic route of 19485-38-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

857070-66-7, name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, 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. name: (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol

A mixture of u-7 (0.0085 mol) and u-6 (0.0255 mol) was stirred at 120C for 4 hours. A 10% solution of K2C03 in water was added. The aqueous layer was saturated with K2C03 (powder). The mixture was extracted with CH2Cl2. The organic layer was separated, dried (over MgS04), filtered and the solvent was evaporated. The residue (4.1 g) was purified by column chromatography over silica gel (eluent: CH2C12/ CH30H/NH4OH 90/10/1; 15-40um). The pure fractions were collected and the solvent was evaporated, yielding 1.6 g of intermediate u-8 (59%).

The synthetic route of 857070-66-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10394-40-8, 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 10394-40-8 as follows.

STR44 An aqueous solution (100 ml) of 3.95 g of 1,6-dimethylbenzimidazole and 10 g of potassium permanganate was stirred at 50 C. for 2 hours and 2 g of potassium permanganate was further added to the mixture. The mixture was stirred at 80 C. for further 2 hours. After insoluble matters were filtered off, the filtrate was rendered pH 4 with 1 N hydrochloric acid and concentrated under reduced pressure to give 7.33 g of 1-methylbenzimidazole-6-carboxylic acid as the mixture with potassium chloride. The above compound was heated to reflux in 150 ml of methanol overnight in the presence of 3 ml of conc. sulfuric acid. The reaction solution was concentrated under reduced pressure and water was added to the concentrate.

According to the analysis of related databases, 10394-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4977175; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem