Month: March 2021

These common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, 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. Quality Control of 1-Methyl-1H-imidazole-4-carbaldehyde

A 10 litre round bottomed flask fitted with an overhead stirrer with a large paddle was charged with 5- bromo-2-(4-chlorobenzoyl)-3-fluorobenzoic acid (178.25 g; 0.5 mol) and anhydrous THF (2610 mL) added. This solution was cooled to -5CPatent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, molecular formula is C12H9F3N2O2, 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. SDS of cas: 641571-13-3

PAL-resin 4-methyl-3-nitro-aniline (5g, 5mmol), bis (2-oxo-3-oxazolidinyl) phosphinic chloride (5.09g, 20mmol), DIEA (3. 5mL, 20mmol), and 3- (4-methyl-imidazol-1-yl)-5- trifluoromethyl-benzoic acid (2. 71g, 10.0mmol) are mixed in DMF (50mL) with shaking at room temperature for 18 hours. The resultant mixture is filtered and the resin is washed with DMF (3x50mL), CH2Cl2 (3x50mL), MeOH (3x50mL), and dried under vacuum. lOmgs of this resin is treated with TFA/CH2Cl2/H20 (45/50/5) (20011L) for 30 minutes. LC-MS shows only one peak: observed MS (M + H+) is 405.1 ; calculated MS (M + H+) is 405.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-13-3, its application will become more common.

Reference:
Patent; IRM LLC; WO2005/39486; (2005); A2;,
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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H6N2O2

To a solution of N-(2,3-dihydrobenzofuran-5-yl)-4-iodopyridin-2-amine (300 mg, 0.88 mmol) in DMF (3 mL) was added methyl 1H-imidazole-4-carboxylate (167 mg, 1.3 mmol), potassium phosphate (564 mg, 2.6 mmol) and L-Proline (20 mg, 0.17 mmol) under a nitrogen atmosphere. The reaction mixture was purged with nitrogen for 10 min, then copper iodide (33 mg, 0.17 mmol) was added, and then the reaction mixture was stirred for 15 h at 140 C. in a sealed glass tube. Reaction mixture was cooled and filtered through Celite, and the filtrate was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure, and the residue was purified by gradient column chromatography using ethyl acetate in n-hexane as eluent to afford methyl 1-(2-((2,3-dihydrobenzofuran-5-yl)amino)pyridin-4-yl)-1H-imidazole-4-carboxylate as a yellow semi-solid (0.10 g, 17%). LC-MS calcd exact mass 336.12, found m/z 337.2 [M+H]+.

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; 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

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. Product Details of 288-32-4

Step 4 4-(Imidazol-1-yl)nitrobenzene To a stirred solution of imidazole (34.1 g, 0.50 mol) in DMF (300 ml) under Ar, was added portionwise, over 23 minutes, 60% NaH in oil (20.02 g, 0.50 mol). The mixture was then stirred at room temperature for 18 minutes before adding dropwise, over 40 minutes, a solution of 1-fluoro-4-nitrobenzene (70.62 g, 0.50 mol) in DMF (60 ml). The mixture was then stirred at room temperature overnight. Water (600 ml) was then added and the solid was filtered off, washed with water, then stirred in boiling ethyl acetate (400 ml), allowed to cool and filtered, washing the solid with more ethyl acetate (50 ml), then petroleum ether (250 ml). The filtrate, now containing more solid, was refiltered and washed with petroleum ether. The combined solids were dried in a vacuum desiccator overnight to give 90.14 g (95%) of the title compound as a yellow solid. deltaH (360 MHz, DMSO-d6) 7.59 (1H, t, J=1.1 Hz), 7.97-8.03 (3H, m), 8.38 (2H, d, J=9.2 Hz), 8.52 (1H, t).

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:
Patent; Merck Sharp & Dohme Ltd.; US6150391; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-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. category: imidazoles-derivatives

In a 1000 ml three-necked flask, equipped with mechanical stirring, Ar gas protection, add 25. lg of the bromine synthesized in the third step (molecular weight 348, 0.072 mol 1), 300 ml of anhydrous THF, cooled to -78 C, stirred 35ml of BuLi (2 ¡¤ 4M, 0.084mol) was added dropwise, the temperature was maintained at _78 C, and after stirring for 10 min, 40 ml of B(0iPr) 3 (molecular weight 188.07, specific gravity 0.9574, 0.204 mol) was added dropwise at -78 C. After stirring to room temperature (with 3 hrs), dilute acid is added to hydrolyze, the aqueous layer is separated, neutralized to neutrality, sodium chloride is added, hydrazine HF dissolved in water is distilled off under reduced pressure, and a white solid is precipitated and filtered to obtain a product. 21 g of solid product, yield 93.41%.

The synthetic route of 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Beijing Weixinnuo Technology Co., Ltd.; Tsinghua University; Li Yinkui; Duan Lian; Fan Hongtao; (34 pag.)CN104513206; (2019); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 96797-15-8, 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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 40.a. (R,S) 4-(Hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl)-benzonitrile A solution of 1-trityl-4-iodoimidazole (3.53g, 8.10mmol) in CH2Cl2 (35ml) was cooled to about -3C under N2 and 3M EtMgBr in Et2O was added dropwise while maintaining reaction temperature at below about 0C. The solution was stirred for about one hour at about 0C and then 4-cyanobenzaldehyde (1.18g, 9.00mmol) was added in one portion and the reaction was allowed to warm to room temperature for about 1 hour.. The reaction mixture was then again cooled to about 0C and 5% HCl (30ml) was added.. The reaction mixture was stirred about 15 min. and then extracted with CH2Cl2 (2x25ml).. The combined CH2Cl2 layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and then concentrated under reduced pressure.. The residue was triturated with EtOAc (25ml) and the product filtered off (2.92g, 82%).. Mass spec. 442.3 MH+, NMR (300MHZ, DMSO-d6, 30C) 7.7-7.8 (2H, d), 7.5-7.6 (2H, d), 7.3-7.5 (9H, m), 7.25-7.3 (1H, s), 7.0-7.15 (6H, m), 6.75-6.8 (1H, s), 5.9-6.90 (1H, m), 5.6-5.7 (1H, m).

The synthetic route of 4-Iodo-1-trityl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.); EP1382607; (2004); A2;,
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. 25676-75-9, name is 4-Bromo-1-methylimidazole, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-methylimidazole

To a solution of compound 121-4 (700 mg, 1.74 mmol, 1.0 eq), compound 121-4a (308 mg, 1.91 mmol, 1.1 eq), Cs2C03 (1.13 g, 3.48 mmol, 2.0 eq) in Dioxane (8 mL) and H20 (2 mL) was added Pd(PPh3)4 (101 mg, 87.0 umol, 0.05 eq) under N2. The reaction mixture was stirred at 90 C for 16 hours. The reaction mixture was concentrated under reduced pressure. The mixture was diluted with water (20 mL) and the resultant mixture was extracted with EA (50 mL * 3). The combined organic layers were dried over Na2SC>4, filtered and concentrated to dryness under reduced pressure. The residue was purified by preparative high performance liquid chromatography. The pure fractions were collected and the volatiles were removed under vacuum. The resulting mixture was lyophilized to dryness to remove the solvent residue completely. The title compound 121-5 (180 mg, 28% yield) was obtained. LCMS (ESI): RT = 0.592 min, mass calcd. for C18H20N4O2S 356.13, m/z found 356.9 [M+H]+, lH NMR (400MHz, CDCI3) delta 9.09 (s, 1H), 7.86 (d, J = 2.3 Hz, 1H), 7.49 (dd, J= 2.3, 8.8 Hz, 1H), 7.46 (s, 1H), 7.41 – 7.30 (m, 4H), 7.29 – 7.26 (m, 2H), 6.62 (d, J = 8.8 Hz, 1H), 4.53 (s, 2H), 4.21 (q, J= 5.4 Hz, 1H), 3.75 (s, 3H), 2.61 (d, J = 5.5 Hz, 3H).

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; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); 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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(1H-Imidazol-1-yl)acetic acid

Example 1 – Zoledronic Acid; EPO A suspension of 1-imidazol-l-yl acetic acid (200 g) in methanesulfonic acid 98-99 % (240 ml) is added slowly and blending phosphorous trichloride (856 ml).The temperature is increased until reaching 55 0C, reflux is observed.Once the phosphorous trichloride aggregate is finished, the aggregate of water (171 ml) is started, thus increasing the exothermy, which is evidenced through a larger volume of reflux.During the reaction hydrogen chloride is released.The mass in suspension slowly dissolves and the solution turns very viscous, thus making the agitation difficult.After 12 hours reaction at 55-70 0C, water is slowly added (805 ml), in a period of 2-3 hours at a temperature between 8 and 25 0C, with which a fluid solution is achieved.It is then heated at 105 – 112 0C over 3 hours and the solution is filtered to eliminate impurities.The resulting solution is partially neutralized at a temperature of 30 – 40 0C with a sodium hydroxide aqueous solution 50 % (w/v) until obtaining a pH of 0.25 +/- 0.03It is then cooled down to 0-5 0C, maintaining this temperature over at least 2 hours the precipitate being filtered.The same is washed by resuspension once in water (500 ml) and twice in methanol (500 ml each time).The precipitate may be dried in a stove at 50 – 60 0C, thus obtaining the raw zoledronic acid with a potentiometric titre equal to or exceeding 98 %.It may also be used humid to prepare the trihydrate form.The output is 83 %.

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; GADOR S.A.; WO2007/16982; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

6-(trifluoromethyl)oxazolo[4,5-c]pyridin-2-amine 5-amino-2-(trifluoromethyl)pyridine-4-ol (220 mg, 1.24 mmol) was dissolved in anhydrous THF (7 mL). Di(1H-imidazol-1-yl)methanimine was then dissolved into the solution. The reaction was stirred at 65 C. for 24 hours. After cooling the solution to room temperature, the solution was taken up in ethyl acetate and washed with deionized water, saturated NH4Cl, and saturated NaCl. The organic layer was dried over MgSO4, filtered, and concentrated down to the crude material. Excess CH2Cl2 was added to the crude solid, which precipitated out. The pure solid was filtered and dried under vacuum. Yield: 91%. 1H NMR (400 MHz, DMSO): 8.58 (s, 1H), 8.17 (s, 2H), 8.02 (s, 1H). [M+1]+=204.1.

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

Reference:
Patent; Indiana University Research and Technology Corporation; The Brigham and Women’s Hospital, Inc.; Androphy, Elliot J.; Hodgetts, Kevin; Calder, Alyssa Nicole; (46 pag.)US2017/239225; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20970-50-7, name is 1-(1-Methyl-1H-imidazol-5-yl)ethanone, 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 20970-50-7, Safety of 1-(1-Methyl-1H-imidazol-5-yl)ethanone

EXAMPLE 3 2-Benzyl-4-(1′-methyl-5′-imidazolyl)thiazole hydrochloride A solution of 5-acetyl-1-methylimidazole (100 mg, 0.81 mmol) in 2.4 ml of acetic acid was stirred at 25 C. as 0.24 ml (0.30 g, 1.2 mmol) of 31% hydrobromic acid in acetic acid was added. Pyridinium bromide perbromide (0.29 g, 0.91 mmol) was added, giving an orange solution from which a yellow precipitate formed after 30 minutes. After 2.5 hours, ether (5 ml) was added. The supernatant was removed by pipet, and the precipitate was dried under a stream of nitrogen. Ethanol (6 ml) and benzylthioamide (137 mg, 0.91 mmol) were added, and the mixture was heated to reflux for 45 minutes. The reaction was cooled to 25 C., poured into 25 ml of ether, and washed with 50 ml of 1.25N aqueous sodium hydroxide. The aqueous layer was extracted with 2*25 ml of ether, and the organic extracts were combined, dried (sodium sulfate), filtered, and evaporated. The residue was purified by column chromatography on silica gel (5 g), eluted with 8% isopropanol in 4:1 dichloromethane/ethyl acetate, yielding 2-benzyl-4-(1′-methyl-5′-imidazolyl)thiazole (159 mg, 77% yield) as an almost colorless oil. The free base (159 mg, 0.62 mmol) was dissolved in 10 ml of methanol and treated with 0.32 ml (0.64 mmol) of 2.0N aqueous hydrochloric acid. Evaporation of the solution yielded 183 mg of pale yellow crystals. Recrystallization from 2:1 ethyl acetate/ethanol gave 2-benzyl-4-(1′-methyl-5′-imidazolyl)thiazole hydrochloride (111 mg, 61% recovery) as colorless plates, m.p. 191-194 C.

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, 1-(1-Methyl-1H-imidazol-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US4746669; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem