Month: January 2021

Reference of 2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A dried pressure tube was charged with 4-bromo-1H-imidazole (100 mg, 667 mumol), tetrahydrofuran (3 ml), N,N-dimethylformamide (2 ml), 2-(methylsulfonyl)-5-(trifluoromethyl)pyridine (150 mg, 667 mumol), and cesium carbonate (261 mg, 800 mumol). The tube was sealed and heated at 105 C. for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 60:30 as the eluent. The 2-(4-bromo-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine (167 mg, 86% yield) was obtained as a crystalline white solid. MS (ISP): m/z=292.0 [M+H]+ and 294.2 [M+2+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-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Narquizian, Robert; Woltering, Thomas; Wostl, Wolfgang; US2012/253035; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13739-48-5, 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. 13739-48-5, name is 2-Methyl-4-phenyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Charged, imidazole (V) (2.529 m. moles), cesium carbonate (3.54 m. moles), cuprous oxide (0.152 m. moles), PEG (2.549 m. moles), 5-bromo-thiophen-2- carboxylic acid amide (1.947 m. moles), 4,7-dimethoxy-l,10-phenanthrolein (0.354 m. moles) to the DMSO (50 ml) in RB flask, and the reaction mixture was heated to 115-1200C and the temperature was maintained for 20 hrs. (Reaction is monitored by TLC). After completion of reaction, cooled to RT, diluted with DCM (250 ml) and filtered on hyflo bed. DCM was evaporated under reduced pressure. To the residue ammonia solution was added and extracted with ethyl acetate (250 ml X 3 times), which was then washed with water and dried over sodium sulfate. Ethyl acetate was evaporated under reduced pressure to get the crude product, which was purified by silica gel column chromatography using DCM: methanol 100 – 5% to get the desired compound (89) in 25 % yield.

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-4-phenyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; GENZYME CORPORATION; WO2009/137081; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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 29043-48-9, COA of Formula: C8H9N3

Example No. 252Preparation of N- (2 -methyl-lH-benzo [d] imidazol-5-yl) -5- (3- (methylsulfonyl) henyl) -IH-pyrazolo [4 , 3-d] pyrimidin-7-amine7-chloro-2- (4-methoxybenzyl) -5- (3- (methylsulfonyl) phenyl) -2H- pyrazolo [4 , 3-d] pyrimidine (0.16 mmol) and 2-methyl-lH- benzo [d] imidazol-5-amine (0.3 mmol 2 eq. , ) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HCl in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 419.1378 g/molHPLC-MS: analytical method Lrt: 3.21 min – found mass: 420 (m/z+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, 2-Methyl-1H-benzoimidazol-5-ylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 18075-64-4,Some common heterocyclic compound, 18075-64-4, name is 1-Phenyl-1H-imidazole-4-carboxylic acid, molecular formula is C10H8N2O2, 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 suspension of (S)-1-([1,2,4]triazolo[4,3-a]pyrazin-8-yl)pyrrolidin-3-amine hydrochloride salt (109 mg, 0.4 mmol) and 1-phenyl-1H-imidazole-4-carboxylic acid (76 mg, 04 mmol) in DMF (5 mL) was added diethylisopropyl amine (650 mg, 5 mmol), followed by HATU (160 mg, 0.41 mmol). The resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 100 mg of the title compound (67% yield) as a white solid. MS: (ES) m/z found 375.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Phenyl-1H-imidazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3314-30-5,Some common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 3-amino-N-({[(3-fluoropyridin-2- yl)methyl]carbamoyl}methyl)propanamide (422) (300 mg , 1 .13 mmol), 1 H-benzimidazole-2-carbaldehyde (214 mg , 1 .47 mmol) and DIPEA (393 muIota, 2.26 mmol) in MeOH (15 ml) at room temperature for 16 h, followed by addition of NaBH4 (64 mg, 1 .69 mmol) gave the title compound (167 mg, 37percent) as a yellow solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.14 (br s, 1 H), 8.44 (t, J = 5.5 Hz, 1 H), 8.36- 8.34 (m, 1 H), 8.32 (t, J = 5.8 Hz, 1 H), 7.69 – 7.63 (m, 1 H), 7.54 – 7.39 (br m, 2H), 7.39 – 7.35 (m, 1 H), 7.14 – 7.08 (m, 2H), 4.46 (dd , J = 5.6, 1 .6 Hz, 2H), 3.90 (s, 2H), 3.77 (d , J = 5.8 Hz, 2H), 2.78 (t, J = 6.6 Hz, 2H), 2.33 (t, J = 6.6 Hz, 2H) HPLCMS (Method G): [m/z]: 385.2 [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 1H-Benzo[d]imidazole-2-carbaldehyde, its application will become more common.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 87233-54-3, name is 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole, 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 87233-54-3, Quality Control of 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole

Combine 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole (22.3 g, 99.4 mmol), 1-methyl[1,4]diazepane (19 mL, 152.8 mmol), and triethylamine (75 mL). Heat to 70 C. After 18 hours, add 1-methyl[1,4]diazepane (10 mL) and continue to heat at reflux. After 96 hours, cool to ambient temperature and partition the reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluding sequentially with 50% ethyl acetate/hexane and then 10% methanol/dichloromethane to give 1-methyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.52 (silica gel, dichloromethane/methanol/concentrated aqueous ammonia, 90/10/0.1).

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; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;,
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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

To 400 mL of N-methyl-2-pyrrolidone, 80.0 g (261 mmol) of compound [1] and 0.43 g (5.2 mmol) of cyclohexene were added, and 43.5 g (366 mmol) of thionyl chloride was added dropwise at 20 to 40 C., followed by 60 C. The temperature was raised and the reaction was carried out for 1 hour. After confirming the reaction end point, a solution prepared by dissolving 63.0 g (261 mmol) of compound [3] in 400 mL of N-methyl-2-pyrrolidone was added dropwise to the reaction mass, and the mixture was reacted at 60 C. for 3 hours. After 400 mL of water was introduced into the reaction mass, the temperature was raised to 80 C, 83.0 g of a 20% KOH aqueous solution was added dropwise, and the temperature was kept at 80 C for 3 hours or more.Subsequently, 112.3 g of a 20% KOH aqueous solution was added dropwise over 1 h. After cooling to 60 C., 45.2 g of a 40% K 2 CO 3 aqueous solution was added dropwise, and the mixture was cooled to 40 C. over about 2 hours. The obtained crystals were dried under reduced pressure to obtain 128.6 g of compound [4] (nilotinib) (yield 93.0%). The area percentage of the peak of the target substance in the LC chromatogram was 99.96% (nuclear chlorinated product was not detected).

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; Sumitomo Chemical Co., Ltd.; Kumazawa, Hiroharu; Akiyama, Masaki; (8 pag.)JP2020/7240; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 693-98-1, 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 693-98-1 as follows.

EXAMPLE 42 2-Methyl-1-(p-nitrophenyl)imidazole A mixture of 50.0 g of p-fluoronitrobenzene, 85.93 g of 2-methylimidazole and 44.9 g of potassium carbonate in 860 ml of dimethylsulfoxide is heated at 120¡ã C. for 24 hours. The mixture is poured into 2.5 liter of water and stored in a refrigerator for two days. The mixture is filtered and cake washed with copious volumes of water and vacuum dried. The cake is dissolved in 1500 ml of ethyl acetate, filtered through hydrous magnesium silicate and the filtrate reduced to about 500 ml, cooled and the resulting solid, filtered, and air dried to give 81.0 g of the desired product as brown crystals, m.p. 135¡ã-137¡ã C.

According to the analysis of related databases, 693-98-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US5128351; (1992); A;; ; Patent; American Cyanamid Company; US5077409; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 72-40-2, 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. 72-40-2 name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, 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.

To a stirred suspension of 5-amino-I H-imidazole-4-carboxamide hydrochloride (1 Og, 0.061 5 mol) in acetonitrile (80 mL) was added diisopropylethylamine [DIPEA (12g. 0.0958 mol)] at room temperature. The reaction mixture was stirred at room temperature for 1 0mm followed by 4-nitrophenyl methylcarbamate (25g, 0.1270 mol) was added. The reaction mixture was stirred at room temperature for 24h. After consumption of starting material, the reaction mixture was filtered and the cake washed with acetonitrile (20 mL). The obtained solid was slurried in acetonitrile (80 mL), filtered and cake washed with acetonitrile (20 mE). The obtained solid dried at room temperature for 24h to afford 5-amino-NI-methyl-i H-imidazole1, 4-dicarboxamide (10 g) as an off white solid.?HNMR (DMSO-d6): 8.41 (q, 1H), 7.59 (s, 1H), 6.86 (bs, IH), 6.77 (bs, 1H), 6.35 (s, 2H), 2.78 (d, J 3.2 Hz. 3H);Mass (ni/z): 183.9 (M+); HPLC purity: 98.13%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-1H-imidazole-4-carboxamide hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; GRANULES INDIA LIMITED; VETUKURI, Prasada Raju VNKV; RAPOLU, Rajesh Kumar; NARAYANA, Rama Krishna Reddy; CHIGURUPATI, Krishna Prasad; CHATURVEDI, Akshay Kant; (20 pag.)WO2018/122724; (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. 73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Iodo-2-methyl-1H-imidazole

PREPARATION 73 1-(3-Methyl-4-nitrophenyl)-4-iodo-2-methylimidazole, m.p. 146-148, was prepared similarly to Preparation 20 using using 4-fluoro-2-methylnitrobenzene, 4-iodo-2-methylimidazole and sodium carbonate as the starting materials with dimethylformamide as the solvent. Analysis %: Found: C, 38.5; H, 3.1; N, 12.4; Calculated for C11 H10 N3 O2 I: C, 38.5; H, 2.9; N, 12.2;

The synthetic route of 73746-45-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4728653; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem