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. 253453-91-7, name is 2-Chloro-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 253453-91-7

To a solution of 2-chloro-1-methyl-1H-imidazole (92.8 g, 796 mmol) (see the Supporting Information for the synthesis) in anhydrous THF (1.8 L) was added dropwise a solution of t-BuLi (336 mL, 2.5 M, 840 mmol) in hexane at -60 C with stirring over 2 h. After the addition, a solution of (SS)-4 (221.6 g, 799 mmol) in anhydrous THF (1.0 L) was added dropwise to the above solution over 1 h at the same temperature. The resulting mixture was warmed from -60 C to r.t. with stirring overnight. TLC (PE-EtOAc, 1:1) showed the expected spot (Rf = 0.3). The mixture was poured into sat. aq NH4Cl (1 L) and extracted with EtOAc (3 × 0.8 L). The organic layers were combined, washed with brine (1 L), dried (Na2SO4), and concentrated. The crude product was purified by flash column chromatography on silica gel (PE-EtOAc, 10:1 ? 2:1) to give the title compound; yield: 189.9 g (60%); yellow solid; Rf = 0.3 (EtOAc-PE, 1:1).

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 253453-91-7.

Reference:
Article; Chen, Yantao; Goldberg, Frederick W.; Xiong, Jian; Wang, Shujun; Synthesis; vol. 47; 5; (2015); p. 679 – 691;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 253453-91-7, The chemical industry reduces the impact on the environment during synthesis 253453-91-7, name is 2-Chloro-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

Example XXIV Preparation of 2-Chloro-3-methyl-3H-imidazole-4-carboxylic acid To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel is added 2-chloro-1-methyl-1H-imidazole (1 equiv.) and THF (0.5 M). The reaction mixture is cooled to -78 C. and n-BuLi (2.5 M in hexanes, 1.05 equiv.) is added. The resulting mixture is stirred for 1 h and a solution of CO2 is bubbled into the solution. After the addition is complete, the cooling bath is removed and the reaction is allowed to warm to rt. The reaction mixture is quenched with satd. aq. NH4Cl, transferred to a separatory funnel, and extracted with EtOAc. The organic layer is washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents are evaporated under reduced pressure to yield the product. The material is purified by recrystallization or column chromatography.

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-Chloro-1-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10394-40-8, 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 10394-40-8 as follows.

STR44 An aqueous solution (100 ml) of 3.95 g of 1,6-dimethylbenzimidazole and 10 g of potassium permanganate was stirred at 50 C. for 2 hours and 2 g of potassium permanganate was further added to the mixture. The mixture was stirred at 80 C. for further 2 hours. After insoluble matters were filtered off, the filtrate was rendered pH 4 with 1 N hydrochloric acid and concentrated under reduced pressure to give 7.33 g of 1-methylbenzimidazole-6-carboxylic acid as the mixture with potassium chloride. The above compound was heated to reflux in 150 ml of methanol overnight in the presence of 3 ml of conc. sulfuric acid. The reaction solution was concentrated under reduced pressure and water was added to the concentrate.

According to the analysis of related databases, 10394-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4977175; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

857070-66-7, name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol

A mixture of u-7 (0.0085 mol) and u-6 (0.0255 mol) was stirred at 120C for 4 hours. A 10% solution of K2C03 in water was added. The aqueous layer was saturated with K2C03 (powder). The mixture was extracted with CH2Cl2. The organic layer was separated, dried (over MgS04), filtered and the solvent was evaporated. The residue (4.1 g) was purified by column chromatography over silica gel (eluent: CH2C12/ CH30H/NH4OH 90/10/1; 15-40um). The pure fractions were collected and the solvent was evaporated, yielding 1.6 g of intermediate u-8 (59%).

The synthetic route of 857070-66-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

19485-38-2, name is 1-Methylimidazole-4,5-dicarboxylic Acid, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 19485-38-2

Example 238 HATU (83 mg, 0.22 mmol) was added to a mixutre of l-methyl-lH-imidazole-4,5- dicarboxylic acid (17.8 mg, 0.10 mmol) and an HCl salt of Intermediate 32 (80 mg, 0.21 mmol) in DMF (1 mL) and DIPEA (0.091 mL, 0.52 mmol) and the reaction mixture was stirred at rt for 16 h. The reaction was filtered and purified by preparative HPLC to afford the title compound (10.5 mg). LC-MS retention time = 2.85 min; m/z = 827.2 [M+H]+. (Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0- 100% B over 3 minutes, then a 0.75-minute hold at 100% B; Flow: 1.0 mL/min;

The synthetic route of 19485-38-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
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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. 169770-25-6, name is Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Methyl-4-nitro-imidazole-2- carboxylate 40 (5 g, 27 mmol) was dissolved in 1 : 1 mixture of MeOH and EtOAc (150 mL). A slurry of moist 10% PdVC in EtOAc was added and the contents were stirred vigorously under hydrogen (70 psi) for 14 h. The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as green solid. The crude amine without any further purification was taken up in CH3CN (150 mL). Contents were cooled to 0 0C and DIEA (6.9 mL, 37.7 mmol) was added. A solution of 1- methyl-4-nitro-2-trichloroacetylpyrrole 23 (7.6 g, 28.2 mmol) in CH3CN (20 mL) was added and the reaction mixture was allowed to stir at ambient temperature for 14 h, EPO during which solid precipitated out. The reaction mixture was filtered to furnish 42 as yellow solid (5 g, 60%). The filtrate was concentrated and the residue was taken up in MeOH. Et2O was added to furnish a second crop of 42 (1 g, 12%). 1H-NMR (DMSO-d6) 611.14 (s, exch, IH, NH), 8.19 (d, IH, J = 1.2 Hz, Py-CH), 7.80 (d, IH, J = 1.2 Hz, Py-CH), 7.68 (s, IH, Im-CH), 3.96 (s, 3H, CH3), 3.94 (s, 3H, CH3), 3.82 (s, 3H, CH3). 13C-NMR (75 MHz, DMSO-d6) 6158.9 (+, s, CO), 157.4 (+, s, CO), 137.1 (+, s, Im-C2), 134.1 (+, s, Py-C4), 131.2 (+, s, Im-C2), 128.2 (-, d, Py-C5), 125.4 (+, s, Py-C2), 1 15.2 (-, d, Im-C5), 1 10.2 (-, d, Py-C3), 52.0 (-, q, OCH3), 37.9 (-, q, CH3), 35.2 (-, q, CH3). EI-HRMS: m/z calcd for Ci3Hi5N5O5 321.1073; found 321.1094 (M+, 20%), 279.0997 (100%), 194.0830 (72%), 153.0317 (35%).

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 169770-25-6.

Reference:
Patent; UNIVERSITY OF SASKATCHEWAN; WO2007/45096; (2007); 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. 177760-04-2, name is Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 177760-04-2

A solution of the amino ester (36.94 g, 0.218 mol) in 200 ml of acetic acid was added drop wise to a solution of sodium nitrite (100 g, 1.449 mol) and water (300 ml) cooled in an ice-water bath, and stirred. The temperature of the reaction mixture, which was measured to be around -5 – 1O0C was raised to rt and and the reaction mixture stirred overnight. The reaction mixture was extracted with DCM (3 x 150 mL). The combined DCM layers were dried and evaporated to yield a reddish residue which was separated by column chromatography on silica gel employing as eluent EA/hexane (30%) to yield 1-N- methyl-2-nitroimidazole-5-carboxylic acid ethyl ester (“nitro ester”) as a light brown solid (27 g, yield 62%).

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 177760-04-2.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2007/2931; (2007); 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. 10394-39-5, name is 5-Methoxy-1-methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxy-1-methyl-1H-benzo[d]imidazole

To a solution of 5-methoxy-l-methyl-lH-benzo[d]imidazole (500 mg, 3.08 mmol) in CH2C12 (6 ml) was added BBr3 (3.1 g, 12.33 mmol) dropwise at 0C. After addition, the mixture was stirred for 2 h at 0C. The mixture was then quenched by slow addition to ice water (50 mL). The resulting mixture was extracted with CH2C12 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the title compound (100 mg, 21.9%) as a white solid which was used in next step without further purification. LCMS (m/z): 149.1 (M+l).

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; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 887571-32-6, These common heterocyclic compound, 887571-32-6, name is N-Methyl-1-(5-methyl-1H-benzo[d]imidazol-2-yl)methanamine, 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.

General procedure: Approximately 0.5 mmol of 2 and 0.5 mmol of HATU were dispensed in 24 reaction wells (MiniBlock XT) using a dispensing spatula and funnel. To each well were added 10 mL of anhydrous MeCN, (0.5 mmol) of the appropriate amine in MeCN, and then 0.13 mL of DIPEA (0.75 mmol) through the septa sheet. The reaction block was covered and shaken at room temperature for 180 minutes (TLC monitored). Two grams of silica gel were added to each well and the reaction block was placed on a parallel centrifugal evaporator. After automated flash chromatography, the obtained pure intermediate (0.25 mmol) and 4 mL of formic acid (50%) were dispensed in 24 reaction wells (MiniBlock XT), heated to 70 C and shaken vigorously for 2 h whereupon TLC showed no remaining starting material. Silica gel (1 g) was added to each well and the mixture was evaporated, dried on a parallel centrifugal evaporator and the dry solid was chromatographed to give the desired product.

Statistics shows that N-Methyl-1-(5-methyl-1H-benzo[d]imidazol-2-yl)methanamine is playing an increasingly important role. we look forward to future research findings about 887571-32-6.

Reference:
Article; Moukha-Chafiq, Omar; Reynolds, Robert C.; Nucleosides, nucleotides and nucleic acids; vol. 33; 11; (2014); p. 709 – 729;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6232-92-4, name is 6-Nitro-1H-benzo[d]imidazol-2-amine, 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. COA of Formula: C7H6N4O2

VIII-1 7-nitropyrimido[1,2-a]benzimidazole hydrochloride and 8-nitropyrimido[1,2-a]benzimidazole hydrochloride (Compounds No. XXVI)A mixture of 2 g (11.2 mmol) of 2-amino-5-nitro-benzimidazole (J. Med. Chem., 1995, 38(20), 4098-4105) and of 3.6 ml (15 mmol) of 1,1,3,3-tetraethoxypropane in 50 ml of ethanol and 2 ml of concentrated hydrochloric acid is refluxed for 12 hours. 1.97 g of a beige precipitate is recovered by filtration and is dried under reduced pressure. A mixture of isomers is obtained, which is used as it is in the subsequent step.

The synthetic route of 6-Nitro-1H-benzo[d]imidazol-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2009/42873; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem