Tag: M.W=100-200

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

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

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

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

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

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

Related Products of 17325-26-7, These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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.

Preparation 121 1-Trityl- 1H-imidazole-4-carboxylic acid methyl ester Add triethylamine (1.88 mL, 13.48 mmol) to a mixture of methyl-4-imidazolecarboxylate (1.0 g, 7.93 mmol) and triphenylmethyl chloride (2.43 g, 8.72 mmol) in anhydrous acetonitrile (25 mL) over 10 min at room temperature and stir overnight. Quench with water and extract with ethyl acetate (3*). Combine the organic layers, wash with 1N hydrochloride solution, water, saturated aqueous sodium bicarbonate solution and brine sequentially, dry over sodium sulfate, and concentrate to provide the title compound 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol).

Statistics shows that Methyl 1H-imidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 17325-26-7.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2849-93-6, These common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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.

0.064 mmol of BENZIMIDAZOLECARBOXYLIC acid 41 was dissolved in DMF together with 0.064 MMOL of the amine 5d, a solution of TBTU (0.096 MMOL) in DMF, HOBT (0.026 MMOL) in DMF and 0.32 MMOL of DIPEA were added successively, and the mixture was stirred at room temperature. After 2.5 hours, 0.2 eq. of acid was added, and the mixture was stirred overnight. After further addition of 0.2 eq. of acid, the reaction mixture was diluted with water after 3 hours, and the resulting precipitate was filtered off with suction, washed with water and digested with diethyl ether. Yield : 76%, pale-beige solid

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

Reference:
Patent; MERCK PATENT GmbH; WO2005/4863; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 54624-57-6, A common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Step 2. 2-(lH-Benzoimidazol-2-yl)-3-cyclohexyl-lH-indole-6-carboxylic acid methyl ester (10.3)A reaction flask was charged with 100 mg (0.26 mmol) 10.2, 64 mg (0.33 mmol, 1.25 eq) 2-bromobenzimidazole and 15 mg (0.013 mmol, 0.05 eq) Pd(PPh3 )4. To this was added 4 mL dioxane and 1 mL NaHCO3 (sat., aq.). The reaction mixture was degassed and purged with Argon (2x), and then gently heated to 90 0C for 4 h. HPLC and LC-MS analysis confirmed complete consumption of 10.2. The reaction mixture was allowed to cool to room temperature and then concentrated. The desired methyl ester was precipitated by addition of cold H2O and collected by centrifuge. 10.3 was dried under vacuum and used without further purification. MS: 374.1 (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; GENELABS TECHNOLOGIES, INC.; WO2008/11521; (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. 35203-44-2, name is 1-Propyl-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Propyl-1H-imidazole

General procedure: A solution of N-alkylimidazole (10 mmol, 2 equivalents) and Dibromoalkane (5 mmol, 1 equivalent) was refluxed in toluene (20 mL) for 24?30 h. The reaction mixture was allowed to cool and toluene was decanted leaving a sticky solid behind. The sticky solid was washed three times with dry THF and finally with diethyl ether once. Solvent was removed under vacuum to get a white amorphous hygroscopic powder (88?94 percent yield). NMR spectra were recorded in D2O and/or DMSO-d6.

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; Aher, Sainath Babaji; Bhagat, Pundlik Rambhau; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5587 – 5596;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem