Tag: M.W=100-200

The chemical industry reduces the impact on the environment during synthesis 872-49-1, name is 5-Chloro-1-methylimidazole, I believe this compound will play a more active role in future production and life. 872-49-1

General procedure: 2-Chloropyrazine(0.64 g, 5.56 mmol), tetrakis(triphenylphosphine) palladium(0)(96 mg, 0.083 mmol), and potassium carbonate (0.77 g,5.56 mmol) were added to a solution of 22 (1.16 g, 2.78 mmol)in a mixed solvent of DMF-EtOH (2 : 1, 18 mL), and the mixturewas stirred at 90C for 2 h. The reaction solution was partitionedbetween water and EtOAc, and the organic layer waswashed with water and brine, dried over anhydrous MgSO4,filtered, and concentrated in vacuo. The residue was purifiedusing silica gel column chromatography (33-67% EtOAc inhexane) to yield 23a (0.79 g, 77%) as a colorless amorphous.

The chemical industry reduces the impact on the environment during synthesis 872-49-1. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yamamoto, Shuji; Shibata, Tsuyoshi; Abe, Kumi; Oda, Koji; Aoki, Takeshi; Kawakita, Yasunori; Kawamoto, Hiroshi; Chemical and Pharmaceutical Bulletin; vol. 64; 9; (2016); p. 1321 – 1337;,
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33468-69-8, name is 4-(Trifluoromethyl)-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. 33468-69-8

Production Example 58 A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-1H-imidazole, 0,55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2-{3-[4-(trifluoromethyl)imidazole-1-yl]pyridin-4-yl}-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 57”). [Show Image] 1H-NMR (CDCl3) delta: 9.00 (d, J=5.2 Hz, 1H), 8,84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8,06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

Statistics shows that 33468-69-8 is playing an increasingly important role. we look forward to future research findings about 4-(Trifluoromethyl)-1H-imidazole.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2274983; (2011); A1;,
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46006-36-4, name is 1H-Benzimidazole-7-carboxylic 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. 46006-36-4

. [148] Into a 50-mL round-bottom flask, was placed lH-l,3-benzodiazole-4-carboxylic acid (42 mg, 0.26 mmol, 1.00 equiv), HATU (164 mg, 0.43 mmol, 1.50 equiv), DIEA (111 mg, 0.86 mmol, 3.00 equiv), 4,5,6,7-tetrahydro-2H-indazol-3-amine dihydrochloride (60.6 mg, 0.29 mmol, 1.10 equiv), N,N- dimethylformamide (5 mL). The resulting solution was stirred overnight at 25 C. The reaction mixture was diluted with DCM (50 mL), washed with H2O (50 mL x 3) and brine (50 mL x 3) and dried with Na2SC>4. After filtration, the filtrate was concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (Analyse HPLC-SHIMADZU): Column: XBridge Shield RP18 OBD Column, 5um, 19* 150mm; Mobile Phase A: water (0.1%FA), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 3% B to 20% B in 17 min; 254 nm. The collected fraction was lyophilized to give 18.5 mg (25%) of (3-amino-4,5,6,7-tetrahydroindazol-2-yl)(lH-benzo[d]imidazol-4-yl)methanone (Example 48) as an off-white solid. Rt= 15.5 min; MS (ES, m/z) [M+H]+: 282; 1HNMR (DMSO- 6, 400MHz, ppm): delta 11.57(s, 1H); 8.71(s, 1H); 8.02(d, J=7.6, 1H); 7.87(d, J=8.0, 1H); 7.47-7.43(m, 1H); 2.61-2.58(m, 2H); 2.45-2.46(m, 2H); 1.76-1.67(m, 4H).

Statistics shows that 46006-36-4 is playing an increasingly important role. we look forward to future research findings about 1H-Benzimidazole-7-carboxylic acid.

Reference:
Patent; THE ROCKEFELLER UNIVERSITY; PONDA, Manish, P.; BRESLOW, Jan, L.; SELNICK, Harold; EGBERTSON, Melissa; (207 pag.)WO2017/205296; (2017); A1;,
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2849-93-6, 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below.

The bispyridine ester amine compound (168 , 0.83 mmol) in Example 1 and benzoimidazole-2-carboxylic acid (190 , 1.17 mmol) were dissolved in DMF (5 ), HBTU (402 , 1.25 mmol) and triethylamine (0.58 , 4.17 mmol) were added to the solution, and the mixture was stirred at room temperature for 24 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a white solid (247 , 86 %) by chromatography (methanol : dichloromethane = 1:30).

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; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/125923; (2009); A2;,
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Adding some certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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 1003-21-0. 1003-21-0

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1.3 M in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C.) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C. in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 2: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C.) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C. with an ice bath and carefully quenched with 2 N aqueous HCl to pH=7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phases split and the organic layer was washed with brine (2*200 mL), dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and suspension was filtered to provide the title compound as a solid.

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 5-Bromo-1-methyl-1H-imidazole.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; US2015/105404; (2015); A1;,
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68282-53-1, 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Example 20 (0253) (rac)-2,4-bis((jE)-2-(4-methyl-lH-imidazo-5-yl)vinyl)-6,7 0 i-tetrahydro- dipyrido[2,l- a:l’,2T-k][2,9]phenanthroHne-5,12-diium trifluoromethanesulfonate, HTA-C5-11Starting racemic helquat O (10.0 mg, 16.3 mupiiotaomicron), 1 -methyl- lH-pyrrole-2-carbaldehyde (57 mg, 522 mupiiotaomicron), pyrrolidine (22 mu, 261 mupiiotaomicron) and dry methanol (0.5 ml) were placed into a 10 ml flask and the resulting mixture was stirred under argon for 1 h at room temperature. Progress of the reaction was monitored by thin layer chromatography. The crude product was precipitated from the reaction mixture by addition of diethylether (5 ml). The suspension was centrifuged and the supernatant was separated from the solid pellet. The solids were dissolved in methanol (0.5 ml) and the pure product was precipitated by addition of diethylether (5 ml). The same procedure was repeated with tetrahydrofuran (0.5 ml) – diethylether (5 ml) and acetonitrile (0.3 ml) – diethylether (5 ml). Then, centrifugation of this suspension, removal of the supernatant and drying of the solid part under vacuum of an oil pump led to 10.1 mg (12.7 muiotaetaomicron, 78 % yield) of dark-yellow solid HTA-C5-1 1. (0255) (0256) NMR (400 MHz, acetonitrile-d3): 2.32 (s, 3H), 2.46 (s, 3H)5 3.12-3.43 (m, 4H), 4.27-4.31 (m, 1H), 4.80-4.88 (m, 2H), 5.05 (m, 1H), 7.01 (d, J= 16.04 Hz, 1H), 7.44-7.52 (m, 4H)} 7.62-7.76 (m, 4H), 7.83-7.96 (m, 2H), 8.13-8.17 (m, 1H), 8.026 (d, J= 1.96 Hz, 1H), 8.77 (dd, J= 2.12, 6.32 Hz, 1H), 10.38 (broad s, 2H for -NH).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; VYSOKA SKOLA CHEMICKO-TECHNOLOGICKA V PRAZE; TEPLY, Filip; HAJEK, Miroslav; KUZMOVA, Erika; KOZAK, Jaroslav; KOMARKOVA, Veronika; HUBALKOVA, Pavla; REYES-GUTIERREZ, Paul Eduardo; JIRASEK, Michael; SONAWANE, Monoj R.; JOSHI, Vishwas D.; SEVERA, Lukas; NOVOTNA, Jana; WO2015/180701; (2015); A1;,
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The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life. 71759-89-2

[0294] Sodium hydride (15.3 g, 385 mmol) was added to a mixture of 4-iodo-lH- imidazole (50 g, 257 mmol) in THF (150 mL) at 0 C. After stirring for 0.5 h, iodomethane (40.0 g, 282 mmol) was added to the solution and the resulting mixture was stirred at room temperature overnight under N2. TLC (DCM / EtOAc = 2/1, v/v) indicated that starting material was consumed and two new spots were formed. The reaction was quenched with MeOH (50 mL), then concentrated to dryness, the residue was purified by silica gel column (DCM / EtOAc = 10/1, v/v) to afford the desired product (higher Rf) (28 g, 52%) as a yellow solid. [0295] 1H NMR (400 MHz, CDCl3) d (ppm): 7.32 (s, 1H), 6.96 (d, 7= 1.2 Hz, 1H), 3.68 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 71759-89-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EPIZYME, INC.; HARVEY, Darren Martin; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; (246 pag.)WO2019/108824; (2019); A1;,
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Imidazole | C3H4N2 – PubChem

872-82-2, 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. 872-82-2 name is 2-(1H-Imidazol-5-yl)ethanol, 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.

4-lmidazoleacetic acid hydrochloride (5.93 g, 36.47 mmol) in methanol (125 mL) was saturated with HCI gas and stirred at room temperature for 5.5 h, then concentrated to give a quantitative yield of 4-imidazoleacetic acid methyl ester hydrochloride as a white solid which had NMR (MeOH- d4) delta 8.87 (d, J = 1.2 Hz, 1H), 7.46 (s, 1 H), 3.89 (s, 2H) 3.72 Patent; PFIZER PRODUCTS INC.; WO2007/34277; (2007); A1;,
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3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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.

Typical procedure for the preparation of Benzimidazolyl-benzimidazole; A solution of benzimidazole-2-aldehyde 1 (0.5 mmol) and diamine 2 (0.5 mmol) in dimethylacetamide (4mL) was stirred at 100 0C for 12h. Solvent was evaporated and residue was purified by preparative HPLC to give benzimidazole derivative 3. 1H NMR (300 MHz, MeOH-doe : S 2.52 (s, 3H), 2.85 (brs, 4H)5 3.25 (brs, 4H)5 7.05-7.15 (m, 2 H), 7.25-7.35 (s overlapped with m, 2 H)5 7.60-7.75 (m, 4H); LCMS mlz 333 (M + H+), ELSD 99percent.

The synthetic route of 3314-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMBRIDGE RESEARCH LABORATORIES, INC.; WO2007/56155; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life. 1003-21-0

Pd(PPh3)4 (55.9 mg, 48.4 mumol) was added to a mixture of 6 (300 mg, 0.484 mmol) and 5-bromo-1-methylimidazole (312 mg, 1.94 mmol) in aqueous Na2CO3 (2 M, 1.0 mL, 2.0 mmol) and anhydrous THF (9.0 mL), and the solution was stirred at room temperature for 15 min. The resulting two-phase system was refluxed under stirring overnight, and was then allowed to cool to room temperature. To this was added water (25 mL), and the mixture was extracted with CHCl3 (50 mL¡Á3). The organic layer was washed with water (25 mL), dried over anhydrous MgSO4, and filtered. After the solvent was removed by evaporation, the residue was subjected to SEC fractionation to obtain 1 (150 mg, 59%) as a bluish white solid. Mp: 188.7-189.1 C. IR (KBr, cm-1): 1339, 1276, 1185, 1110, 1055, 989. 1H NMR (500 MHz, CDCl3): delta 7.51 (s, br, 2H, ArH), 7.15 (d, J=1.1Hz, 2H, ArH), 7.00 (s, 2H, ArH), 3.68 (s, 6H, NCH3), 2.02 (s, 6H, CH3). 13C NMR (125 MHz, CDCl3): delta 142.1, 139.8, 129.7, 129.3, 125.7, 125.6, 125.4, 32.7, 14.4. MS (ESI+): m/z=529 [M+H]+. Anal. Calcd for C23H18F6N4S2: C, 52.27; H, 3.43; N, 10.60. Found: C, 52.03; H, 3.46; N, 10.54.

The chemical industry reduces the impact on the environment during synthesis 1003-21-0. I believe this compound will play a more active role in future production and life.

Reference:
Article; Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji; Tetrahedron; vol. 69; 52; (2013); p. 11064 – 11069;,
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Imidazole | C3H4N2 – PubChem