Tag: M.W=100-200

2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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. Product Details of 2466-76-4

[00123] Methyl 2-(2-bromophenyl)-3-oxobutanoate: A round bottom flask was charged with a magnetic stir bar and methyl 2- (2-bromophenyl) acetate (25 g, 109 mmol) and THF (50 mL). This solution was cooled to -78 ¡ãC before drop wise addition of a 1M solution of LiHMDS in THF (218 ml, 218 mmol). The reaction was stirred for 30 min at -78 ¡ãC before addition of l-(lH-imidazol-l-yl)ethanone (14.42 g, 131 mmol) as a solution in a mixture of THF:DMF (112 mL THF, 24 mL DMF). The solution was stirred for 1 h before quenching with sat’d aqueous NH4C1 (-250 mL) and diluting with EtOAc. The layers were separated and the aqueous phase was extracted with additional EtOAc (~2 x 250 mL). The combined organic extract was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography using an eluent of ethyl acetate/hexanes (10: 1) to afford methyl 2-(2-bromophenyl)-3-oxobutanoate (32.5 g, 102 mmol, 93 percent ield).

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NASVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2015/23915; (2015); A1;,
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Related Products of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-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.

General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Luo, Yu; Xiao, Feng; Qian, Shijing; Lu, Wei; Yang, Bo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 417 – 422;,
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Synthetic Route of 3304-70-9,Some common heterocyclic compound, 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, molecular formula is C7H8N2O4, 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 dimethyl 1H-imidazole-4,5-dicarboxylate (1.58g) in water (15mL), was added bromine (4.11g). The mixture was stirred at 60C for Ihr.The solvent was evaporated in vacuo and the residue was triturated with ether to give the target compound (2.35g) as a solid.NMR (DMSO-d6) : d 3.81(6H, s).MASS m/z : 286 (M-l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 4,5-imidazoledicarboxylate, its application will become more common.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; WO2004/108730; (2004); A1;,
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Reference of 15813-08-8,Some common heterocyclic compound, 15813-08-8, name is 5-Bromo-4-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

PREPARATION 705-Bromo-1 ,4-dimethyl-1 H-imidazole To a cooled (0 C) suspension of sodium hydride (60% wt / wt in mineral oil, 149 mg, 3.73 mmol, 1.2 eq.) in anhydrous tetrahydrofuran (10 ml_), under an atmosphere of nitrogen, was added a solution of 5-bromo-4-methyl-1 H-imidazole (500 mg, 3.11 mmol) in tetrahydrofuran (5 ml_). The resulting mixture was stirred at room temperature for 30 min before adding methyl iodide (661 mg, 4.66 mmol, 1.5 eq.). The reaction mixture was stirred for 30 min before partitioning between ethyl acetate (100 ml_) and water (20 ml_). The organic phase was dried over magnesium sulphate and the resulting mixture filtered. The filtrate was evaporated under reduced pressure and the resulting residue purified by chromatography on silica gel (40 g) eluting with a gradient of methanol in dichloromethane (0:100 to 5:95) to give the title compound as a clear oil (80 mg, 15%). 1H NMR (400 MHz, CDCI3): delta = 2.10 (s, 3H), 3.59 (s, 3H), 7.53 (s, 1 H)MS: APCI+ m /z = 174, 176 [MH+]

The synthetic route of 15813-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
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Electric Literature of 10040-98-9, The chemical industry reduces the impact on the environment during synthesis 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, I believe this compound will play a more active role in future production and life.

A mixture of malonitrile (60.0 mg, 0.90 mmol) and 4-(1H-imidazol-1- yl)benzaldehyde (155.0 mg, 0.90 mmol) in anhydrous ethanol ( 4.0 mL) was charged with N- methylmorpholine (0.1 mL, 0.90 mmol) for 2 minutes. To the mixture was added 3-(4- methoxyphenyl)-1-methyl-1H-pyrazol-5(4H)-one (185.0 mg, 0.90 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 48 hrs. The suspension was filtered under vacuum and off white solid was obtained. The solid was gently washed with hexanes (20 mL) and chilled ethanol (10 mL) and further dried under high vacuum to provide compound 48 as an off white solid (360 mg, 94%).1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.18 (s, 1H), 7.68 (s, 1H), 7.52-7.46 (m, 4H), 7.27 (d, J = 8.0 Hz, 2H), 7.13 (s, 2H), 7.06 (s, 1H), 6.78 (d, J = 8.0 Hz, 2H), 5.06 (s, 1H), 3.77 (s, 3H), 3.69 (s, 3H). MS (ESI): Calcd for C24H20N6O2: 424, found: 424 (M+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, 4-Imidazol-1-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; YU, Chengzhi; POLAT, Tulay; YAN, Chao; RABIZADEH, Shahrooz; THEODORESCU, Daniel; (108 pag.)WO2016/205460; (2016); A1;,
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Application of 26832-08-6, These common heterocyclic compound, 26832-08-6, name is 1H-Imidazole-4-carboxamide, 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.

In a dried 125 mL, three-neck flask fitted with a magnetic stirrer, temperature probe, a reflux condenser, and a positive nitrogen atmosphere set-up was charged with 4-imidazole carboxamide 2.0 gm (18 mmol), acetonitrile 25 ml, and POCl3 6.6 gm (43.2 mmol). The brown slurry was agitated and heated to reflux. The reaction mixture was maintained at reflux for at least 15 hrs. Then the excess POCl3 was distilled under reduced pressure. After aqueous work up, the reaction mixture was adjusted to a pH of 9-11 using 25percent sodium hydroxide, and extracted with 4.x.70 ml ethyl acetate. The combine ethyl acetate extracts were treated with 20 gm silica gel, distilled under pressure to remove ethyl acetate and to afford 4-cyanoimidazole as a white solid. After drying the 4-cyanoimidazole weighed 1.1 gm (65.9percent yield): HPLC purity, >99.0 area percent; 1H NMR (300 MHz, DMSO-D6) delta 7.89 (s, 1H), 8.08 (s, 1H); 13C NMR (300 MHz, DMSO-D6) delta 111.8, 116.0, 127, 138.1.

Statistics shows that 1H-Imidazole-4-carboxamide is playing an increasingly important role. we look forward to future research findings about 26832-08-6.

Reference:
Patent; Ampac Fine Chemicals LLC; US2009/292122; (2009); A1;,
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Reference of 33468-69-8, The chemical industry reduces the impact on the environment during synthesis 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

0.6 g of intermediate 2-3, 4- (trifluoromethyl) imidazole 0.36 g and toluene 0.74 g of potassium carbonate,0.26 mL of trans-N, N’-dimethylcyclohexane-1,2-diamine and 0.15 g of copper iodide were added.The reaction mixture was stirred at 120 C. for 24 hours,After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate.The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 3: 2) to obtain 0.32 g of the active compound A-12 shown below.

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, 4-(Trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; MURAKAMI, SHINICHIRO; (291 pag.)JP2018/76354; (2018); A;,
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137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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: 137049-00-4

General procedure: 2-Aminoethyl amine (1 equiv.) and 2-trifluormethyl-4-fluoro benzonitrile(1 equiv.) were dissolved under argon in dry MeCN, followedby addition of Et3N (1.5 equiv). The resulting reaction mixture wasstirred at 50 C for 4 h. After cooling to room temperature water andCH2Cl2 were added, followed by thorough extraction. The combinedorganic layer was dried over Na2SO4, filtered and concentrated underreduced pressure to afford desired 4-[(2-aminoethyl)-amino]-2-(trifluormethyl)benzonitrile. 4-[(2-aminoethyl)-amino]-2-(trifluormethyl)benzonitrile (160 mg, 0.69 mmol) was dissolved in a flame-dried roundbottomedflask in CH2Cl2 (20 mL) under argon and diisopropylethylamine (0.37 mL, 2.09 mmol) was added. After stirring at room temperaturefor 5 min a solution of the corresponding aryl- or hetarylsulfonylchloride (0.69 mmol) in dry CH2Cl2 (5 mL) was added, andthe resulting reaction mixture was stirred at room temperature for20 h¡¤H2O and CH2Cl2 were added, followed by thorough extraction. Thecombined organic layer was dried over Na2SO4, filtered, concentratedunder reduced pressure and purified via column chromatography(heptane/EtOAc, gradient 10:0 to 1:1) to afford desired N-(2-{[4-cyano-3-(trifluormethyl)phenyl]amino}-ethyl)-aryl-/hetaryl sulfonamide 9i-z.

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Frackenpohl, Jens; Schneider, Linn; Decker, Luka J.B.; Dittgen, Jan; Fenkl, Franz; Fischer, Christian; Franke, Jana; Freigang, Joerg; Getachew, Rahel; Gonzalez Fernandez-Nino, Susana M.; Helmke, Hendrik; Hills, Martin J.; Hohmann, Sabine; Kleemann, Jochen; Kurowski, Karoline; Lange, Gudrun; Luemmen, Peter; Meyering, Nicole; Poree, Fabien; Schmutzler, Dirk; Wrede, Sebastian; Bioorganic and Medicinal Chemistry; vol. 27; 24; (2019);,
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Reference of 137049-00-4, 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 137049-00-4 as follows.

To a solution of 2-chloro-1-(1 /-/-indol-3-yl)-2-phenylethanone (0.200 g; 0.741 mmol) in DMF (5 mL) cooled to 0 C was added sodium hydride (60% dispersion in mineral oil; 0.053 g; 1.333 mmol). The reaction mixture was stirred at room temperature for 0.5 h. 1-Methyl-1 H- imidazole-4-sulfonyl chloride (0.268 g; 1.484 mmol) and DMAP (0.005 g; 0.037 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (30% to 100%) in heptane furnished 0.301 g (98%) of 2-chloro-1-(1-((1-methyl-1 /-/-imidazol-4-yl)sulfonyl)-1 H-indol- 3-yl)-2-phenylethanone as a solid. ESI/APCI(+): 414 (M+H); 436 (M+Na). ESI/APCI(-): 412 (M- H).

According to the analysis of related databases, 137049-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
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Synthetic Route of 3034-38-6, 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 3034-38-6 as follows.

4-nitroimidazole (25 g, 221 mmol), sodium bicarbonate (37.1 g, 442 mmol) and water (600 mL) for dilution and then bromine (30 mL, 620 mmol) the temperature at the dropwise addition and the reaction mixture was at 40 C and reacted for 12 hours. After filtering the solids level of the reaction mixture was washed with toluene three times and dried under reduced pressure to give a yield of 2,5-dibromo-4-nitroimidazole of 39.8 g (67%). Prepared 2,5-di-bromo-4-nitroimidazole (39.8 g, 149 mmol) and water (450 mL) and then diluted to sodium iodide (223 g, 1486 mmol) was added and stirring under reflux was 12 sigan. Lower the temperature to room temperature, then filtered washing the solids in the reaction mixture with water, dried under reduced pressure to yield 2-bromo-5-iodo of 37.6 g (80%) was obtained a 4-nitroimidazole. Prepared 2-bromo-5-iodo-4- nitroimidazole (20 g, 63 mmol) in ethanol (190 mL) and then diluted in triethylamine (26.5 mL, 190 mmol) and platinum oxide (108 mg, 0.47 mmol) to give the applied wave after reacting for 3 hours under a hydrogen pressure of 3 bar in the reactor was concentrated under a reduced pressure after filtration with a silica gel and celite. Yield of the reaction mixture with 2-ethyl acetate 10% washed with hydrochloric acid solution to remove the moisture of the obtained organic layer over anhydrous magnesium sulfate, and then the filtrate was concentrated under reduced pressure and isopropyl alcohol and hexane, to obtain 7.9 g (65%) and then diluted with to give a-bromo-4-nitroimidazole.

According to the analysis of related databases, 3034-38-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Research Institute of Chemical Technology; Kim, Phill Ho; Lee, Sang Ho; Kim, Soo Hyun; Lee, Ir Young; Yoon, Chang Soo; Oh, Tae Kwon; Cho, Sang Rae; (18 pag.)KR101650716; (2016); B1;,
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