Imidazoles-derivatives

Related Products of 693-98-1, 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 693-98-1 as follows.

Step 3aIodine (18.5 g, 73.1 mmol) was dissolved in 90 mL of chloroform. 2-Methylimidazole (3.0 g, 36.5 mmol) in 90 mL of 2M NaOH solution was added slowly.The cloudy mixture cleared to two phases by 2.5 h.The layers were separated and acetic acid (10.5 mL, 183 mmol) was added to the organic layer to neutralize the reaction (to pH~5-6).A solid appeared which was filtered off and recrystallized from warm acetonitrile to afford 8.5 g (69percent) of 4,5-diiodo-2-methyl-1H-imidazole. (M+H)+=334.

According to the analysis of related databases, 693-98-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5805-57-2, A common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, molecular formula is C8H9N3, 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 mixture of 6,9-dichloro-2-methoyl-anzacridine (278 mg,1 mmol) and benzimidazoles (220 mg, 1 mmol) was heated in phenolunder 120 C for 2 h with nitrogen protection. Then the mixturewas poured into ethyl acetate to give yellow precipitates,which were purified by washing with ethyl acetate twice. 4.1.2.1. 6-Chloro-2methyl-9-((1H-benzo[d]imidazol-2-yl)methyl)-azaacridine (9). Yield 73%; mp: 289-291 C; 1H NMR (400 MHz,DMSO-d6) d 8.51-8.48 (d, J = 14.4 Hz 1H), 8.37 (s, 1H), 8.13-8.11(d, 1H), 7.92 (s, 1H), 7.47-7.42 (m, 3H), 7.22-7.20 (d, J = 8.8 Hz,1H), 7.12-7.10 (m, 2H), 3.81 (s, 3H). 13C NMR (101 MHz, DMSOd6)d 157.82, 153.67, 147.62, 146.32, 143.49, 140.36, 140.33, 140.28, 133.72, 127.24, 126.19, 125.45, 123.24, 118.35, 115.08,53.37, 44.72. HRMS (ESI): [M+H]+ 390.1043; found 390.1115.

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, Dan; Yuan, Zigao; Chen, Shaopeng; Zhang, Cunlong; Song, Lu; Gao, Chunmei; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3437 – 3446;,
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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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(Trifluoromethyl)-1H-imidazole

EXAMPLE 1 2-(2,4-Dichlorophenyl)-1-(1,2,4-triazol-1-yl)-3-(5-trifluoromethylimidazol-1-yl)-propan-2-ol A mixture of 4-trifluoromethylimidazole (0.7 g, 5 mmole), 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-oxirane mesylate salt (1.88 g, 5 mmole) and anhydrous potassium carbonate (2.0 g, 14 mmole) in dry N,N-dimethylformamide (20 ml) was heated at 75-80 C. for 18 hours. The solvent was evaporated under vacuum and the residue was partitioned between water (20 ml) and methylene chloride (50 ml). The aqueous layer was separated and extracted twice with methylene chloride (30 ml). The organic layers were combined, dried over magnesium sulphate and evaporated to yield the crude product containing the 4- and 5-trifluoromethyl-imidazolyl isomers. The residue was chromatographed on silica eluding with a mixture of hexane, isopropyl alcohol and concentrated ammonium hydroxide (80:20:1.5); fractions containing the minor component were evaporated and the product recrystallized from a mixture of acetone and water to give the desired title compound (0.02 g, 1%), m.p. 190-192 C. C14 H12 Cl2 F3 N5 O requires C, 44.3; H, 3.0; N, 17.2%. Found: C, 44.5; H, 3.1; N, 17.3%.

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; Pfizer Inc.; US4554286; (1985); A;,
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;,
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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 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

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 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

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

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. 918321-20-7, name is Methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate

A solution of Pd(OAc)2 (0.777 g, 3.46 mmol, 0.04 equiv.) and Xantphos (3.0 g, 5.19 mmol, 0.06 equiv.) in toluene (300 mL), under N2 was stirred for 20 minutes and then added to a slurry of 6-amino-7-fluoro-3-methyl-5H-benzoimidazole-5-carboxylic acid methyl ester (6) (19.3 g, 86.5 mmol, 1 equiv.), bromochloroiodobenzene (30.2 g, 95.1 mmol, 1.1 equiv.) and Cs2CO3 (particle size = 20 microns or less; 51 g, 156 mmol, 1.8 equiv.) in toluene (200 mL), over 15 minutes at about 50 0C. The mixture was then heated at reflux for 29 hours, after which no starting material remained by HPLC analysis. After allowing the mixture to cool to ambient it was filtered through an M frit and the solid was washed with toluene (95 mL), then dried in a vacuum oven at 50 0C overnight. The solid was then suspended in water (784 mL) and 2N aqueous HCl (174 mL) was added slowly, over about 15 minutes to control bubbling. The resultant slurry was stirred at room temperature for 2 hours, then filtered through an M frit funnel (150 mL). The solid product was washed with water (3 x 87 mL) and dried in a vacuum oven at 45 0C, to provide 6-(4-bromo-2- EPO chlorophenylaminoj-V-fluoro-S-metliyl-SH-benzoimidazole-S-carboxylic acid methyl ester (11) 25.6 g (92 wt % by HPLC, corrected mass = 23.6 g, 66% yield). 1H NMR (400 MHz, d6 DMSO) delta 3.84 (3H, s, NMe), 3.93 (3H, s, OMe), 6.44 (IH, dd, J 8.8, 5.1, Ar-H), 7.28 (IH, dd, J 2, 9.8, Ar-H), 7.64 (IH, d J2.1, Ar-H), 8.1 (IH, s, NH) 8.14 ( IH, s, Ar-H), 8.5 (IH5 s, Ar-H); delta 19F (376 MHz, d6 DMSO) -133; 13C NMR (100 MHz, d6 DMSO) delta 32 (MeN), 52 (MeO), 109.4 (C), 109.7 (CH), 115.7 (CH), 119.1 (C), 120.7 (C), 122.5 (C, d, J 10), 130.4 (CH), 131.0 (CH), 133.4 (C, d, J 10), 135.5 (C, d, J 16), 140.8 (C), 146.0 (C-F, d, J 252), 148.6 (CH), 166.7 (COO); v^/cm”1 3401, 1700, 1506, 1274; m/z 412 and 414 (M+ and M+2) detected with MS APCI (+).

According to the analysis of related databases, 918321-20-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; ASTRAZENECA AB; WO2007/2157; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem