Tag: M.W=200-300

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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H24N2

(2) Add 50 mL of ethanol to a four-neck round bottom flask.Further added 19.35 g (0.05 mol) of N,N-dimethyl(1-bromopropyl)decyl ammonium bromide, 10.42 g (0.05 mol)N-decylimidazole and1 g of tetrabutylammonium bromide,The mixture was heated to 70 C with stirring, and the reaction was stirred for 36 hours, and then ethanol was distilled off under reduced pressure.The solid was washed three times with chloroform.The filter cake was vacuum dried at 60 C for 5 hours to obtain a crude product;The crude product is recrystallized three times in acetone to obtain the product.1-(N,N-dimethylammonium alkylammonium) propyl-3-hydrazinium imidazolium dibromide,The yield was 85.8%.

The synthetic route of 33529-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University of Light Industry; Yang Xuzhao; Wang Jun; Li Yakun; Ping Dan; Zhang Yingying; Wu Shide; (8 pag.)CN109970657; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-16-5, 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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 13 (210 mg, 0.63 mmol), 5-bromothiazole (156 mg, 0.95 mmol), SPhos (26.0 mg, 0.06 mmol), SPhos-Pd-G2 (45.7 mg, 0.06 mmol) and 2 M aq. Cs2CO3 solution (0.793 ml, 1.59 mmol) in DME (4 mL) was heated at 130 °C for 1 h under microwave irradiation. The mixture was diluted with EtOAc (10 mL), dried over MgSO4, and solvent removed under vacuum. The residue was purified by column chromatography (NH silica gel, eluted with 5?17percent EtOAc/hexane) to yield (E)-tert-butyl 3-(4-(thiazol-5-yl)pyridin-3-yl)acrylate (14a tBu ester, 102 mg, 56percent) as a pale yellow solid. This compound was dissolved in TFA (2.0 ml) and stirred at rt for 2 h. After removal of solvent under reduced pressure, the residue was triturated with EtOAc/hexane (1:1) (3 mL) and the resulting precipitate collected by filtation to yield 14a TFA salt (79 mg, 36percent overall) as a colorless solid

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-1-methyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Fujimoto, Jun; Hirayama, Takaharu; Hirata, Yasuhiro; Hikichi, Yukiko; Murai, Saomi; Hasegawa, Maki; Hasegawa, Yuka; Yonemori, Kazuko; Hata, Akito; Aoyama, Kazunobu; Cary, Douglas R.; Bioorganic and Medicinal Chemistry; vol. 25; 12; (2017); p. 3018 – 3033;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Method B, Step 3: (7aS,12a1R)-10-fluoro-3-(3-methoxy-4-(4-methyl-1 H- imidazol-1 -yl)styryl)-6,7,7a,8-tetrahydro-5H-indeno[1 ,2- b][1,2,4]oxadiazolo[4,5-a]pyridine (B3, R9 = 4-(4-Methylimidazol-1-yl), R10 = 3- MeO-Phenyl) B2 (0.24g, 0.63mmole) was dissolved in THF and the reaction was cooled to -78C. n-Butyllithium (2.5ml in Hexane, 0.28ml) was added and the reaction was stirred at -78C for 30 minutes. 3-methoxy-4-(4-methyl-1 H-imidazol-1- yl)benzaldehyde (0.136g, 0.63mmole) in 10 ml THF (Pre-cooled to -78C) was added. The reaction was stirred at -78C for 1 hour, then at room temperature for one hour. THF was removed and the residue was partitioned between 100ml EtOAc and 100ml water. The organic layer was washed with water (2x100ml), dried with Na2SO4 and concentrated. The residue was purified by column (EtOAc/hexane from 25/75 to 100/0 in 45 minutes, 12Og silica). Yield: 0.19g, 68%. 1H NMR (CDCI3400 MHz): 7.73 (s, 1 H), 7.50 (dd, J = 8.1 , 5.12 Hz, 1 H), 7.43 (d, J = 16.8 Hz, 1 H), 7.27 (m, 1 H), 7.18 (d, J = 8.1 Hz, 1 H), 7.13 (s, 1 H), 7.00 (m, 3H), 6.52 (d, J =16.1 Hz, 1 H), 3.90 (s, 3H), 3.71 (m, 1 H), 3.30 (dd, J = 16.1 and 5.9 Hz, 1 H), 2.91 (m, 1 H), 2.64 (m, 1 H), 2.38 (d, J = 16.1 Hz, 1 H), 2.30 (s, 3H), 2.06, (m, 1 H), 1.51 (m, 2H), 1.10 (m, 1 H). MS (M+1 ): 445.2.

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2008/153792; (2008); 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. 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

To a solution of methyl 2-ethoxy-lH-benzo[d]imidazole-7-carboxylate (55.5 mg, 0.252 mmol) in DMF (2 mL) was added sodium hydride (60percent) (16.78 mg, 0.420 mmol) at RT. The reaction mixture was stirred for 10 min at RT before methyl 4″-(bromomethyl)- [l,l’:3′, l”-terphenyl]-4′-carboxylate (Intermediate 400b, 80 mg, 0.210 mmol) was added in its own solution of DMF (1 niL). After 50 min of stirring at RT the reaction mixture was diluted with EtOAc and washed with 10percent LiCl (aq). The organic phase was dried over MgS04, filtered over celite, and concentrated. The residue was dissolved DMF and purified by ISCO (0-100percent EtOAc/Hexanes) to afford the title compound (Intermediate 314a, 48 mg, 0.069 mmol, 33.0 percent yield). LC-MS Retention time (Method A2) = 1.20 min. Found m/z: 520.1 (M+H)+. H NMR (400MHz, CDC13) delta 7.89 (d, 7=8.1 Hz, 1H), 7.66 – 7.57 (m, 4H), 7.55 – 7.49 (m, 2H), 7.49 – 7.31 (m, 4H), 7.22 (d, 7=8.4 Hz, 2H), 7.01 (d, 7=8.1 Hz, 2H), 5.66 (s, 2H), 4.68 (q, 7=7.1 Hz, 2H), 3.78 (s, 3H), 3.57 (s, 3H), 1.54 – 1.48 (m, 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; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3,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.

(VII) (10 g), t-butanol (300 mL), triethylamine (7.9 g) and diphenylphosphoryl azide (11.2 g) were added to a 500 mL reaction flask. The mixture was heated to reflux and refluxed for 16 hours then cooled to room temperature. The solvent was removed by evaporation under reduced pressure. The residue was treated with water (150 mL) and extracted with ethyl acetate (2 x 150 mL). The extracts were combined, washed with brine (150 mL), dried over sodium sulfate and evaporated to remove the solvent under reduced pressure to give the crude product (12.5 g).The above crude product (12.5 g), n-propanol (125 mL), p-xylene (125 mL) and solid sodium hydroxide (7.3 g) were added to a 500 mL reaction flask. The mixture was stirred and the mixture was heated to reflux and refluxed for 30 hours. Stirring was stopped, water (162 mL) was added and the azeotrope was distilled off under reduced pressure. The residue was diluted with water (20 mL), cooled to 0 & lt; 0 & gt; C, stirred slowly for 1 h and filtered. The filter cake was washed with water (2 x 30 mL) and dried in vacuo at 55 C to give 7.1 g of the solid compound (I). The HPLC purity was 98.7% and the overall yield of the two-step reaction was 79.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, its application will become more common.

Reference:
Patent; Esteve Huayi Pharmaceutical Co., Ltd; Zhao, Liqiang; Wang, Zhao; Jiang, Hong; Dong, Jin; Xu, Xiaofei; Zheng, Guorong; (9 pag.)CN105985293; (2016); A;,
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. 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 95470-42-1

Ethyl 2-bromo-1-(cyclopropylmethyl)-4-methyl-1H-imidazole-5-carboxylate (EV-AT8650-001)? Step 2 To ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (EV-AT8648-001, 550 mg, 2.36 mmol) in DMF (10 ml), was added potassium carbonate (652 mg, 4.72 mmol) followed by (bromomethyl)cyclopropane (0.25 ml, 2.60 mmol) and the reaction mixture stirred at room temperature for 16h. Saturated aqueous ammonium chloride (150 ml) was added to the reaction mixture and the aqueous layer was extracted with ethyl acetate (2×150 ml). The combined organics were then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (0-100percent ethyl acetate/heptane) to afford 543 mg (80percent) of ethyl 2-bromo-1-(cyclopropylmethyl)-4-methyl-1H-imidazole-5-carboxylate (EV- AT8650-001) as a colourless oil. LCMS (method D): retention time 1.23 min, M/z = 287/289 (M + 1).

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; PADLOCK THERAPEUTICS, INC.; DEVRAJ, Rajesh; KUMARAVEL, Gnanasambandam; ATTON, Holly; BEAUMONT, Edward; GADOULEAU, Elise; GLEAVE, Laura; KERRY, Philip Stephen; LECCI, Cristina; MENICONI, Mirco; MONCK, Nat; PALFREY, Jordan; PAPADOPOULOS, Kostas; TYE, Heather; WOODS, Philip A.; (158 pag.)WO2017/147102; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. Computed Properties of C11H10F3N3

Methyl 3-((tert-butoxycarbonyl)amino)-4-methylbenzoate (Intermediate A, 39.8 g, 0.15 mol, 1.5 eq.),3-(4-Methyl-1-1H-imidazole)-5-trifluoromethylaniline (starting material SM2, 24.1 g, 0.1 mol, 1.0 eq.) and N,N-dimethylformamide (250 ML).The reaction mixture was cooled to -10 to 0 C, and potassium t-butoxide (56.1 g, 0.5 mol, 5.0 eq.) was added to the reaction mixture and stirred for 2 to 3 hours.The reaction was monitored by high performance liquid chromatography, and water (100 mL) was added to the reaction mixture.A 3N aqueous hydrochloric acid solution was added to the system to adjust the pH to 7-8. filter,The filter cake is dried to give 2-methyl-5-((3-(4-methyl-1-1H-imidazole)-5-(trifluoromethylphenyl)carbamoylphenyl)carbamic acid tert-butyl 45.1 g of ester (intermediate B),A crude white to yellow solid with a purity of 94.8% and a molar yield of 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-11-1, its application will become more common.

Reference:
Patent; Shanghai Fu Xingxing Tai Pharmaceutical Technology Co., Ltd.; Liu Xuejun; Chen Xiaodong; Hao Lu; Wu Feng; (23 pag.)CN109666023; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 870837-18-6, These common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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.

To a THF (40 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (4.00 g) obtained in Example 1, diethylphosphonoacetic acid ethyl ester (4.00 mL) and lithium hydroxide monohydrate (932 mg) were added one by one, and the reaction solution was agitated overnight at room temperature. 2N sodium hydroxide solution (30 mL) and ethanol (5 mL) were added to the reaction solution after confirming disappearance of the starting materials, and the reaction solution was agitated at room temperature overnight. The reaction solution was cooled to 0 C., 2N hydrochloric acid (30 mL) was added to the reaction solution, and the precipitation consequently deposited was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.61 g of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.81 (s, 1H), 7.60 (d, J=16 Hz, 1H), 7.56 (s, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.16 (s, 1H), 6.66 (d, J=16 Hz, 1H), 3.88 (s, 3H), 2.15 (s, 3H).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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: C13H9N3

5/-/-Benzo[c/]benzo[4,5]imidazo[1 ,2-a] imidazole (15.0 g, 72.4 mmol), 4-iodo- 1 ,1 ‘-biphenyl (20.3 g, 72.4 mmol), K3P04 (46.1 g, 217 mmol) and copper(l) iodide (2.76 g, 14.5 mmol) are suspended in 1 ,4-dioxane (750 ml) under argon. The mixture is degassed and heated up to 100 C while stirring. trans- 1 ,2-Diaminocyclohexane (75 ml) is added and stirring at 100 C is continued for four days. Then, the reaction mixture is cooled to room temperature and 5% ammonia in water (600 ml) is added. The precipitate is filtered off. The solid is washed with 5% ammonia in water, pure water, ethanol and heptane. The crude product is dried in vacuo. A grey powder (23 g, 64.0 mmol, 88%) is obtained. (0201) GC-MS (El, 70 eV) = 359 (100%) Synthesized accordingly are the following products using the respective starting materials (SM):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28890-99-5, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; STENGEL, Ilona; MAIER-FLAIG, Florian; HARBACH, Philipp; MONTENEGRO, Elvira; LUDEMANN, Aurelie; (0 pag.)WO2019/170691; (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. 864076-05-1, name is Methyl 4-bromo-1-methyl-1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 864076-05-1

To a suspension of methylamine hydrochloride (78.6 mg, 1.16 mmol, Eq: 3) in dioxane (3.88 ml) was added dropwise 2 M trimethylaluminum in toluene (582 mu, 1.16 mmol, Eq: 3) (slight gas evolution) and the mixture was stirred for 30 minutes at room temperature. Then methyl 4- bromo-1 -methyl-1H-imidazole-2-carboxylate (0.085 g, 388 muiotaetaomicron, Eq: 1) was added and the mixture was heated to reflux overnight. The reaction mixture was quenched with 120 ul of water (strong gas evolution) and the mixture was stirred for 15 minutes at room temperature. Then sodium sulfate was added and the stirring was continued for 1 hour. The suspension was filtered and washed with dichloromethane and dichloromethane/methanol 9: 1. The obtained solution was concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the desired product as a white solid (51 mg, 60 percent). MS (m/z) = 218.1, 220.1 [(M+H)+].

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GAUFRETEAU, Delphine; KOLCZEWSKI, Sabine; PLANCHER, Jean-Marc; STOLL, Theodor; HALM, Remy; (85 pag.)WO2017/76852; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem