Category: imidazoles-derivatives

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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 1H-imidazole-5-carboxylate

To a stirred solution of methyl 4-imidazolecarboxylate (CAS Number 17325-26-7; 0.500 g,3.97 mmol) and 1,10-phenanthroline (1.400 g, 7.94 mmol) in DMSO (5 ml) was added iodobenzene(1.600 g, 7.94 mmol), Cs2CO3 (3.800 g, 11.9 mmol) and Cu20 (0.567 g, 3.97 mmol) at rt in a microwave tube. The reaction mixture was heated at 100C for 15 mm in microwave. The resulting reaction mixture was cooled to rt and filtered. The obtained filtrate was diluted with water (60 ml) and extracted with EtOAc (3 x 60 ml). The combined organic layer was dried over Na2SO4, filtered andconcentrated under reduced pressure yielding methyl 1 -phenyl- 1H-imidazole-4-carboxylate (0.450 g,2.23 mmol). This material was directly used for next step without any further purification. LCMS:Method C, 2.066 mi MS: ES+ 203.00.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark Ian; STOCKLEY, Martin Lee; MADIN, Andrew; (95 pag.)WO2017/103614; (2017); 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 7098-07-9 as follows. 7098-07-9

General procedure: To a vigorously stirred solution of imidazole derivatives (23.39mmol) in dry toluene (10mL) at room temperature was added the solution of chloromethyl-salicylaldehydes 2a, b (19.50mmol) in dry toluene (10mL), drop-wise, under nitrogen atmosphere. The resulting solution was further stirred at 60°C for 24h. The product separated out was washed twice with toluene (2×5mL) and several times with ether (5×10mL), to remove the unreacted materials, and dried under vacuum to give pale yellow solid which used for the following preparations without further purification. Samples of the products were nevertheless isolated and fully characterized, as described below.

According to the analysis of related databases, 7098-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elshaarawy, Reda F.M.; Janiak, Christoph; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 31 – 42;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 60-56-0, 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: {2-[4-(1-Methyl-imidazol-2-ylsulfanylmethyl)-benzoylamino]-phenyl}-carbamic acid tert-butyl ester (Compound 138) To a solution of N-methyl-2-mercaptoimidazole (28 mg, 0.25 mmol) in THF (1 mL), at r.t. under N2 atmosphere were successively added 137 (70 mg, 0.20 mmol), triphenylphosphine (70 mg, 0.27 mmol) followed by dropwise addition of diethyl azodicarboxylate (48 muL, 0.31 mmol). The mixture was stirred for 2 h and the solvent was removed in vacuo. Purification by flash chromatography using MeOH/CHCl3 (5:95) as the eluent afforded the title compound 138 (81 mg), in 91% yield, which was found to contain some diethyl hydrazodicarboxylate residus. The compound was used as is without further purification.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-2(3H)-thione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MethylGene, Inc.; US6897220; (2005); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[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. Formula: C19H20N4

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, 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 288-32-4 as follows.

General procedure: This compound was synthesized using a variation of the procedure previously reported [32]. Sodium hydride (60% dispersion in mineral oil, 1.56 g, 39.0 mmol) was suspended in dry THF (50 mL) under Ar at 0 C. Imidazole (2.16 g, 31.7 mmol) was dissolved in dry THF (20 mL) and added drop-wise. After 30 min, 1-bromodecane (5.41 g, 24.5 mmol) was added. The resulting reaction mixture was then stirred at room temperature overnight. After careful addition of a few drops of water to quench the remaining sodium hydride, the organic solvent was removed in vacuo, and diethyl ether (50 mL) was added. This solution was then washed with water (3 × 50 mL), dried over anhydrous MgSO4, filtered, concentrated, and then purified by flash chromatography (ethyl acetate/hexanes = 10/1 (v/v)) to give the product as a light yellow oil (yield: 4.38 g, 86%). Spectroscopic and purity data matched those reported for this compound [32].

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shi, Zhangxing; Newell, Brian S.; Bailey, Travis S.; Gin, Douglas L.; Polymer; vol. 55; 26; (2014); p. 6664 – 6671;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 864076-05-1, These common heterocyclic compound, 864076-05-1, name is Methyl 4-bromo-1-methyl-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.

A solution of (3^)-3-hydroxy-l-methyl-3-[2-[3-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)phenyl]ethynyl]pyrrolidin-2-one (73 mg., 0.21 mmol), methyl 4-bromo-l- methyl-lh-imidazole-2-carboxylate (40 mg, 0.18 mmol), cesium fluoride (54 mg, 0.36 mmol) and bis(triphenylphosphine)palladium(II) dichloride (12.5 mg, 0.018 mmol) in ethanol (1.5 mL) and water (1.0 mL) was degassed. The reaction mixture was heated in microwave at 100 °C for 45 min. The reaction was filtered through celite. The crude product was purified by flash chromatography (MeOH/DCM) then submitted for rHPLC to give product (27 mg, 42.7percent). LC-MS (ES, m/z): 354 [M+H]+.

The synthetic route of 864076-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, A common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, molecular formula is C8H7ClN2O, 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 33 2-Chloro-5-methoxy-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole 2-Chloro-5-methoxy-1H-benzimidazole (0.661 g, 3.6 mmol) was coupled to 1,2,3-tri-O-acetyl-5deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (9:1 methylene chloride/ether) to yield the title compound (0.900 g, 65%) as a ~1:1 mix of regioisomers (1H NMR); MS (AP): m/z 405 (M+Na); 1H NMR (DMSO-d6) delta: 7.65-7.54 (two d, 1H), 7.21 (s, 1H), 6.97 (m, 1H), 6.18-6.11 (two d, 1H), 5.70-5.59 (m, 1H), 5.21 (q, 1H), 4.27 (m, 1H), 3.83 (two s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.51 (t, 3H).

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Glaxo Wellcome Inc.; US6413938; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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. Application In Synthesis of 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

The synthetic route of 1,1′-Sulfonyldiimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 144690-33-5, The chemical industry reduces the impact on the environment during synthesis 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

In the equipped with electric stirrer, condenser and a thermometer of the 500 ml three-necked flask, add 20.00g (27.93mmol) intermediate I, 3.13g (55.87mmol) KOH and 80g acetone, for 55 C stirring for 3 hours (TLC monitoring), after the stop of the reaction, to cool down to 20 – 30 C, concentrated to no longer under the dripped, for 1M hydrochloric acid to adjust the pH=3, a large number of white solid precipitated, stirring at the room temperature 1 – 2h, filtering, the filter cake drying added 60 ml ethyl acetate at room temperature beating, filtering, the filter cake is dried to obtain the 11.50g impurities (see Figure 3) F, HPLC: 98.55%, yield: 59.77%.

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, Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsingtao Yellow Sea Pharmaceutical Co., Ltd.; Liu Chuanfei; Chen Xiaotao; Li Yanshun; Wang Jiahui; Liu Ningning; Yang Kebao; (15 pag.)CN106831727; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-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.

EXAMPLE 15 Ethyl 1-[(2′-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (Compound No. 1-119) Following a procedure similar to that described in Example 1(a), but using 0.845 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) and 1.22 g of t-butyl 4′-bromomethylbiphenyl-2-carboxylate, 1.31 g of the title compound were obtained as a gum. This compound was allowed to stand at room temperature, which caused it to crystallize. It was then recrystallized from a mixture of diisopropyl ether and hexane, to give pure title compound, melting at 90-91 C. Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.97 (3H, triplet, J=7 Hz); 1.23 (3H, triplet, J=7 Hz); 1.25 (9H, singlet); 1.60 (6H, singlet); 1.82 (2H, sextet, J=7 Hz); 2.67 (2H, triplet, J=7 Hz); 4.24 (2H, quartet, J=7 Hz); 5.51 (2H, singlet); 5.72 (1H, singlet); 6.87-7.85 (8H, multiplet).

Statistics shows that Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 144689-93-0.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem