Tag: M.W=100-200

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. 17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H8N2O

To a solution of intermediate 111 (400mg, 1. [02MMOL)] in DMF [(20ML)] was added portionwise sodium hydride (60percent in mineral oil, 101mg, 2. [55MMOL)] and the mixture was stirred at room temperature for 20 minutes. Intermediate 22 (173mg, 1. [32MMOL)] was then added and the mixture was heated at [60¡ãC] for 3 days and then poured into water. After extraction with [CH2CI2,] the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with [CH2CI2/MEOH] (90: 10). After trituration with diisopropyl oxide, the title compound was obtained as a yellow solid (130mg, 26percent); m. p. [217¡ãC] ; TOF MS ES + exact mass calculated for [C3OH26N6O] : 487.2246 (MH+). Found: [487. 2247] (MH+).

According to the analysis of related databases, 17289-25-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13135; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, molecular formula is C8H6N2O3, 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. HPLC of Formula: C8H6N2O3

To a stirred solution of 2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carboxylic acid56 150 mg) and methyl indoline-4-carboxylate114 (149 mg) in methanol (5 ml) was added 4-(4,6- dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride 115 (280 mg, DMTMM). The reaction muxture was stirred for 4 h at room temperature. LC/MS analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuo and the residue was purified by preparative reverse-phase HPLC (Gemini NX CI 8, 12 nm, 5mu, 100 x 30 mm, flow rate 40 ml/min, eluant: CH3CN/H2O containing formic acid) followed by lyophilisation in vacuo to afford methyl l-(2-oxo-2,3-dihydro-lH-benzo[d]imidazole-5-carbonyl)indoline-4-carboxylate (60 mg, 21%) as a white solid. MS (ISP): 338.1 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 23814-14-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 22884-10-2,Some common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, molecular formula is C5H6N2O2, 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 (3- { [(ethylimino)methylidene] amino } propyl)dimethylamine hydrochloride (EDC.HC1) (1.2 mmol), 1-hydroxybenzotriazole (HOBt) (1.2 mmol), N,N-diisopropylethylamine (0.35 ml, 2 mmol), 2-(1H-imidazol-1-yl)acetic acid (1.2 mmol), and 3-methyl-4-phenylaniline (1 mmol) in dimethylformamide (7 mL) was stirred for 36 hours at room temperature. Then the reaction mixture was treated withwater (35 mL), the crude product was filtered and purified by recrystallization from acetonitrile. Yield: 40%.The spectral data for Compound 30 is listed below: Compound 30:?HNMR(DMSO-d6): 5= 10.55 (s, 1H,NI]), 7.65 (s, 1H, CmidH), 7.45 (m, 4H, Cp,J]), 7.37 (m, 3H, CFhH) ,7. 17 (m, 2H, CFhH, CmiciH), 6.9 (d, 1H, CmiciH), 4.9 (s, 2H, CH2), 2.2 (s, 3H, CH3) ppm.LS-MS (m/z): calcd./found for [M+H] 292.16. 1/292.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Imidazol-1-yl)acetic acid, its application will become more common.

Reference:
Patent; MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH; SPRINGER, Wolfdieter; FIESEL, Fabienne C.; CAULFIELD, Thomas R.; (172 pag.)WO2018/23029; (2018); A1;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Starting from the o-phenylenediamine compound (1.0equiv) and glycolic acid (2.0equiv), the reaction was refluxed in the presence of a 4.0 mol/L aqueous hydrochloric acid solution, and the TLC was traced until the reaction of the starting material was complete, and the reaction solution was cooled. To room temperature,Adjusting the pH to 7 with 20% NaOH, standing to precipitate a solid, suction filtration, and drying to obtain compound 5; transferring compound 5 to a round bottom flask,Add NaOH aqueous solution,KMnO4 (2.5 equiv) was added in portions at 80 C with stirring, and the reaction was continued after the addition.After all the raw materials were completely reacted, the reaction solution was cooled to room temperature, and the filtrate was filtered by suction.Adjust the pH to neutral with 20% aqueous HCl solution to precipitate a solid.Drying by suction filtration to obtain compound 6;Compound 6 with DMF(1.0equiv) dissolved, then added 1-hydroxybenzotriazole (HOBt, 1.1equiv)And 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 equiv),The reaction was stirred at room temperature for 30 min, and then compound 4 (1.1 equiv) was added to the reaction solution.Continue to stir the reaction,The TLC traces to the completion of the reaction of the starting material, and the reaction solution is poured into ice water.It was then extracted with ethyl acetate and the organic layer was evaporated.The crude product was purified by column chromatography to give the allyl intermediates Sb.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Jiang Xiaoding; (74 pag.)CN109336887; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 25676-75-9, name is 4-Bromo-1-methylimidazole, 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 25676-75-9, Product Details of 25676-75-9

c) To a dry, N2 purged, 500 mL three neck flask equipped with a stir bar is added 200 mL of dry diethyl ether and 4-bromo-N-methylimidazole (50.0 g, 311 mmol). The flask is then cooled to -10 C. with an acetone/ice bath. A 2.0 M heptane/THF/ethylbenzene solution of lithium diisopropylamide (171 mL, 342 mmol) is then added via syringe while maintaining the reaction temperature at 0 C. or lower. After 1 hour, dimethylformamide (DMF) (36.1 mL, 466 mmol) is added dropwise over 5 minutes. The reaction mixture is allowed to stir for 45 minutes at or below 5 C. and then quenched with a saturated aqueous solution of citric acid. The resulting mixture is stirred vigorously until the two phases separate. The organic layer is recovered and washed (3*200 mL) with water. The solvent is removed in vacuo to give the desired product, 2-formyl-4-bromo-(1) N-methylimidazole, as a brown crystalline solid (yield: 55.7 g, 95 percent, 86 percent purity by GC). Additional purification may be achieved by elution through alumina using methylene chloride solvent.

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-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vosejpka, Paul C.; Boone, Harold W.; Frazier, Kevin A.; Iverson, Carl N.; US2009/69567; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5710171; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17286-47-4, 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. 17286-47-4, name is 2-(1H-Imidazol-2-yl)ethanamine dihydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-bromo-lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid(200 mg, 0.830 mmol) in DMF (15 mL) was added hydroxybenzotriazole (HOBt) (224 mg, 1.66 mmol), EDOHC1 (318 mg, 1.66 mmol), TEA (420 mg, 4.15 mmol, 0.58m), the reaction mixture was stirred at 50 C for 0.5 hour, then added 2-(lH-imidazol-2-yl) ethanamine (305 mg, 1.66 mmol, 2 HC1 salt) into it and continued stirred for another 2.5 h to give a pale yellow suspension. LCMS showed the purity of the desired product (Rt = 0.600 min; MS Calc?d: 333.0; MS Found: 333.9 [M+H]+). The mixture was diluted with water (15 mL), then extracted with EtOAc (20 mL x2), the combined extracts was washed with brine (25 mL x2), dried over Na2S04, filtered and concentrated under reduced pressure to give N-(2-(lH-imidazol-2- yl)ethyl)-4-bromo-lH-pynOlo[2,3-b]pyridine-2-carboxamide (250 mg, purity: 92%, yield: 83%) as an off-white solid NMR (400 MHz, DMSO-r e) d 2.86-2.95 (2H, m), 3.52-3.65 (2H, m), 6.85-6.98 (2H, m), 7.15 (1H, s), 7.42 (1H, d, J= 5.2 Hz), 8.19 (1H, d, J= 4.8 Hz), 8.83 (1H, br s), 11.82 (1H, br s), 12.56 (1H, br s).

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

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; RAVI, Kannan Karukurichi; LINDSTROeM, Johan; PERSSON, Lars Boukharta; LIVENDAHL, Madeleine; VIKLUND, Jenny; GINMAN, Tobias; FORSBLOM, Rickard; RAHM, Fredrik; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (478 pag.)WO2019/126733; (2019); 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. 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Amino-1H-imidazole-4-carboxamide hydrochloride

4-amino-5-imidazolecarboxamide hydrochloride was heated to reflux in phosphorus oxychloride for 3.5hs and after purification gave 4-amino-5-nitrile imidazole. This was resuspended in ethanol saturated with HCl overnight and purification gave 4-amino-5-ethylimino ester imidazole hydrochloride. This was combined with diphenylborinic acid ethanolamine ester in tetrahydrofuran (THF) overnight to yield the title compound.

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 72-40-2.

Reference:
Patent; The Penn State Research Foundation; EP1420021; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 137049-00-4, 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. 137049-00-4 name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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.

0.07 g (0.21 mmol) of (R,3r)-3-((7S,8R)-7-(azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclobutanamine were dissolved in dichloromethane, 0.05 g (0.41 mmol) dimethylaminopyridine were added, followed by 0.04 g (0.21 mmol) of 1-methyl-1H-imidazole-4-sulfonyl chloride. The mixture was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and aqueous bicarbonate solution. The aqueous phase was discarded and the organic phase was washed again with aqueous bicarbonate solution, then twice with aqueous ammoniumchloride solution (10%). The organic phase was dried over MgSO4 and evaporated to dryness. The desired product was obtained as a light brown resin (0.01 g, 0.01 mmol, 7%). ESI-MS [M+H+]=491 Calculated for C28H34N4O2S=490.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-4-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Amberg, Wilhelm; Pohlki, Frauke; Lange, Udo; Wang, Ying; Brewer, Jason; Vasudevan, Anil; Lao, Yanbin; Hutchins, Charles; Zhao, Hongyu; Li, Huan-Qiu; US2015/111875; (2015); A1;,
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. 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, A new synthetic method of this compound is introduced below., name: 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile

General procedure: 4.1.6. General procedure E: removal of SEM group To a solution of SEM-protected compound (1.0 equiv) in THFwas added TBAF (3.0 equiv, 1 M in THF). The mixture was reuxedfor 11-20 h, then cooled to room temperature, and concentratedunder reduced pressure. The residue was puried by silica gel col-umn chromatography or PTLC to afford the product.

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; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem