Tag: M.W=100-200

Synthetic Route of 71759-89-2,Some common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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: Method B: In a20 mL microwave Biotage tube, a 1M Na2CO3 aqueous solution(5 mL) purged with argon were introduced into a mixture purged with argon of 4-iodo-1H-imidazole (1a) (0.194 g, 1.0 mmol), a boronicacid 2 (1.6 mmol) and Pd(PPh3)4 (0.80 g, 0.05 mmol) in DMF (15 mL). The mixture washeated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3j and 3p-3u in yields ranging from 30 to 95%. Time and temperaturereactions were collected in Table 1.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
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. 90871-47-9, name is 2-Amino-1-isopropylbenzimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-1-isopropylbenzimidazole

General procedure: Sodium (0.29 g, 12.5 mmol) was dissolved in 15 mL of anhydrous ethanol and this solution was concentrated to a small volume (2-3 mL), then 5.0 mmol of the proper 1-substituted 1H-benzimidazol-2-amine 8 and 50.0 mmol (8.00 g) of diethyl malonate were added and the resulting mixture was heated at 150 C (under reflux) with stirring for 3 h. After cooling, the sodium salt of compound 9, which precipitated as a whitish solid during the reaction, was collected, crushed in a mortar, suspended in Et2O, filtered and dried. This solid was then dissolved in water and the resulting solution was acidified with an excess of 6 N aq HCl (or carefully acidified with 6 N aq HCl down to pH 4, in the case of the pyridyl derivatives compounds 9h-k): this way compounds 9a-k separated out as white or whitish solids that were collected by filtration, washed with water, dried and crystallized from the proper solvent. Only in the case of compounds 9l-o (bearing a tertiary amino group on the side chain), the aqueous solution of sodium salt was treated with an excess of 70% aq. HClO4 to get the precipitation of compounds 9l-o as water-insoluble perchlorates which were collected by filtration, washed with water, dried and crystallized from ethanol. According to this procedure the following compounds 9 were obtained (IR and 1H NMR data are reported only for the new compounds).

The synthetic route of 90871-47-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Di Braccio, Mario; Grossi, Giancarlo; Signorello, Maria Grazia; Leoncini, Giuliana; Cichero, Elena; Fossa, Paola; Alfei, Silvana; Damonte, Gianluca; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 564 – 578;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2466-76-4, 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. 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 3; Preparation of N-I (lS, 2R)-l- (3, 5-difluorobenzyl) -2- hydroxy-3- [ (6-iodo-3, 4-dihydro-2H-chromen-4- yl) amino] propyl} acetamide; Tert-butyl (1S, 2R)-1- (3, 5-difluorobenzyl)-2-hydroxy-3- [ (6-iodo- 3,4-dihydro-2H-chromen-4-yl) amino] propylcarbamate (3.0 g, 5.2 mmol) was dissolved in 30 mL of 25percent TFA/CH2Cl2 and stirred at room temperature for 30 min. The mixture was diluted with CH2Cl2 50 mL and washed with NaHC03 (2 x 30 mL). The organic layer was washed with brine (1 x 50 mL) and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue dissolved in 52 mL of CH2Cl2. The mixture was chilled to 0¡ãC followed by the addition of Et3N (1. mL, 11.9 mmol) and acetyl imidazole (0.68 g, 6.2 mmol). The mixture was warm spontaneously over night. The CH2Cl2 was removed in vacuo and the residue dissolved in EtOAc (100 mL) and washed with 1N HC1 (2 x 30 mL), NaHC03 (1 x 30 mL), brine, dried over Na2SO4, and conc. in vacuo to yield 2. 5 g (92percent) of the title compound as a light yellow solid.

The synthetic route of 1-(1H-Imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7, A common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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.

To a solution of 2,4-dichloro-5-methylpyridine (1.285 g, 7.93 mmol) in DMF (15 mL) were added methyl 1H-imidazole-4-carboxylate (1 g, 7. 93 mmol) and K2CO3 (5.476 g, 39.68 mmol), and then the mixture was stirred at 100 C. for 6 h. The mixture was cooled and diluted with water, and the solid that formed was removed by filtration and dried to obtain crude product. The crude product was purified by Biotage Isolera (using 50% ethyl acetate in hexane as eluent) to obtain methyl 1-(2-chloro-5-methylpyridin-4-yl)-1H-imidazole-4-carboxylate (0.670 g, 34%). 1HNMR (400 MHz, CDCl3): delta 8.44 (s, 1H), 7.79 (s, 1H), 7.69 (s, 1H), 7.27 1H), 3.94 (s, 3H), 2.28 (s, 3H). LC-MS calcd exact mass 251.05, found m/z 252.1 [M+H]+.

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asana Biosciences, LLC; Venkatesan, Aranapakam M.; Thompson, Scott K.; Smith, Roger A.; Reddy, Sanjeeva P.; (166 pag.)US2016/362407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1074-59-5, 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 1074-59-5 as follows.

(S)-N-(l-(5-chloro-4-(4-hydroxy-2-oxo-l,2-dihydroquinolin-6-yl)-lH-imidazol-2- yl)-2-phenylethyl)-3-(lH-imidazol-4-yl)propanamide, trifluoroacetic acid salt [00286] To a solution of 65G (50 mg, 0.131 mmol) in DMF (5 mL) were added3-(lH-imidazol-4-yl)propanoic acid (18.40 mg, 0.131 mmol), DIEA (0.115 mL, 0.656 mmol) and BOP reagent (69.7 mg, 0.158 mmol). The reaction mixture was stirred under N2 at rt. for 2 h. The crude product was purified by reverse phase HPLC(MeOHTH2O with 0.1% TFA). Most of the solvent was removed from the desired fraction, and the product was lyophilized to afford Example 79 as a white solid ((7.6 mg, 7.92%). 1HNMR (400 MHz, CD3OD) delta: 2.55 – 2.66 (m, 2 H), 2.95 (m, 2 H), 3.08 – 3.19 (m, 1 H), 3.21 – 3.27 (m, 1 H), 5.21 (t, /=7.69 Hz, 1 H), 5.93 (s, 1 H), 7.14 (s, 1 H), 7.17 – 7.28 (m, 5 H), 7.39 (d, /=8.79 Hz, 1 H), 7.85 (dd, /=8.57, 1.98 Hz, 1 H), 8.22 (d, /=1.76 Hz, 1 H), 8.73 (s, 1 H). LCMS m/z 502.99 (M+H)+.

According to the analysis of related databases, 1074-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/70826; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 89532-38-7, name is 2-Cyclopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Cyclopropyl-1H-imidazole

Synthesis of ethyl 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-(2-cyclopropyl-1H-imidazol-1-yl)phenyl)-1H-pyrrol-2-yl)propanoate (34B, Ar1-X=4-bromophenyl, Ar2 is 2-cyclopropyl-1H-imidazol-1-yl, R1=4-carbamoyl-2-methylphenyl To a mixture of 34A (Ar2=4-bromophenyl) (455 mg, 1.0 mmol) and 2-cyclopropyl-1H-imidazole (see Method 14 for synthesis) (324 mg, 3.0 mmol, 3.0 eq) in NMP (4 mL) was added 8-hydroxyquinoline (22 mg, 0.15 mmol, 0.15 eq), Cu2O (282 mg, 0.1 mmol) and K2CO3 (166 mg, 1.2 mmol) and PEG-2000 (50 mg). The resultant mixture under N2 was irradiated under microwave at 128 C. for 6.0 h, cooled to room temperature and diluted with THF (10 mL) and water (10 mL). The mixture was filtered and the resultant aqueous layer was extracted with EA (30 mL*5). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, concentrated and purified by silica gel column chromatography (MeOH:CH2Cl2=1:15) to afford the desired compound as a yellow solid (190 mg, yield 39%).

The synthetic route of 89532-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 167487-83-4, These common heterocyclic compound, 167487-83-4, name is Ethyl 1H-benzo[d]imidazole-7-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.

Step 2: ethyl 1-(3-tert-butoxycarbonylamino-3-methyl-butyl)-1H-benzimidazole-4-carboxylate; 0.502 g (12.6 mmol) sodium hydride (60% in mineral oil) are added batchwise at 5 C. to 3.09 g (13.9 mmol) ethyl 1H-benzimidazole-4-carboxylate in 15 mL dimethylformamide and stirred for 30 minutes at ambient temperature. The reaction mixture is then combined with 1.75 g (9.20 mmol) tert-butyl (3-chloro-1,1-dimethyl-propyl)-carbamate and 0.310 g (0.840 mmol) tetraabutylammonium iodide and stirred for 24 hours at 60 C. The reaction mixture is poured into ice water and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried on sodium sulphate and concentrated by evaporation in the rotary evaporator. The residue is purified by reversed-phase flash column chromatography {Varian Microsorb C18-reverse-phase [acetonitrile (0.1% trifluoroacetic acid)/water (0.13% trifluoroacetic acid)=10:90?100:0]}, thus obtaining 0.850 g (2.26 mmol, 16%) ethyl 1-(3-tert-butoxycarbonylamino-3-methyl-butyl)-1H-benzim idazole-4-carboxylate. Rf=0.48 [silica gel, dichloromethane/methanol/ammonia (95/5/0.1)]MS [ESI (M+H)+]=376

Statistics shows that Ethyl 1H-benzo[d]imidazole-7-carboxylate is playing an increasingly important role. we look forward to future research findings about 167487-83-4.

Reference:
Patent; Trieselmann, Thomas; Walter, Rainer; Netherton, Matthew R.; Santagostino, Marco; Hamilton, Bradford S.; US2007/112033; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-31-8, name is 5-Chloro-1H-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. COA of Formula: C3H3ClN2

Example 11 : Preparation of 3-f5-(4-chloroimidazol-1-yl)-2-ethylphenyllbicvclo[3.2.1loctane-2.4- dione and 3-f5-(5-chloroimidazol-1-yl)-2-ethylphenyllbicvclor3.2,Hoctane-2,4-dione3-(5-Bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione (100mg, 0.31 mmol), 4-chloroimidazole (47mg, 0.46mmol), potassium phosphate (264mg, 1.24mmol), L-proline (36mg, 0.31 mmol) and copper (I) iodide (60mg, 0.31 mmol) are combined in a microwave vial, suspended in DMSO and heated under microwave irradiation at 1600C for 45 minutes. The mixture is filtered and purified by preparative reverse-phase HPLC to give a mixture of 3-[5-(4-chloroimidazol-1-yl)-2- ethylphenyl]bicyclo[3.2.1]octane-2,4-dione and 3-[5-(5-chloroimidazol-1-yl)-2-ethylphenyl]- bicyclo[3.2.1 ]octane-2,4-dione.

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA LIMITED; WO2008/145336; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 22884-10-2, A common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic 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.

To a 50 mL flask was added 4-chloro-orthozide 1b (1 mmol), alpha-bromo-tert-butyl ketone (1.2 mmol), and potassium carbonate (1.5 mmol), which was reacted at 45 C, and the reaction solvent was chloroform ( 20mL), after 2 hours of reaction, Further, diphenylmethylphosphine (1.5 mmol) was added, and the reaction was carried out at 30 C. After the reaction was continued for 3 hours, the solvent chloroform was removed under reduced pressure, and the residue was transferred to triphenylphosphine (2.5 mmol) and iodine. (2.5 mmol) in chloroform (15 mL), Then, imidazoleacetic acid (1.5 mmol) was added, and the reaction was carried out at 45 C for 2 hours. After the reaction was completed, the solvent chloroform was removed under reduced pressure. Column chromatography on residue gave 0.228 g of the title compound 2b.

The synthetic route of 22884-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Three Gorges University; Wang Long; Yang Qingqing; Li Yongshuang; Li Dejiang; (8 pag.)CN109265448; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic 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 22884-10-2, Computed Properties of C5H6N2O2

Imidazol-1-ylacetic acid (50 gm), phosphorous acid (150 gm) and n-octane (1000 mL) were taken in a four necked round bottom flask fitted with an addition funnel, mechanical stirrer, condenser and thermometer pocket and allowed to stir at 90-95 C. Phosphorus trichloride (250 gm) was then added to the reaction mixture and allowed to heat at 90-95 C.The reaction mixture was cooled and distilled water (500 mL) was added to it. The reaction mixture was further heated to 90-95 C. and then cooled to room temperature, filtered through celite bed. Aqueous layer was separated and methanol (2000 mL) was added to it. The solution was cooled to 0-5 C. and stirred for 4-5 hrs. he precipitated solid was filtered, washed with methanol and dried under vacuum yielding 70 gm of product.

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-(1H-Imidazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pandey, Satish Chandra; Haider, Hussain; Saxena, Sudhanshu; Singh, Manoj Kumar; Thaper, Rajesh Kumar; Dubey, Sushil Kumar; US2009/312551; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem