Month: September 2021

These common heterocyclic compound, 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, 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

6-chloro-N-[(2,4-dimethylthiazol-5-yl)methyl]-5-methyl-2-methylsulfonyl-pyrimidin-4-amine F5 (480 mg, 1.384mmol) and 3-(1H-benzimidazol-2-yl)propan-1-ol (244 mg, 1.38 mmol) were placed in a 20 mL vial and dissolved in THF(5 mL). AIM solution of NaHMDS in THF (1.38 mL, 1.38 mmol) was added, and the reaction was stirred overnight.Solvent was then removed, and the product was purified by silica gel flash column chromatography (EtOAc/hexanesgradient). 500 mg (82%) of F6 were isolated as an off-white foam. 1H NMR delta (300 MHz, DMSO-d6): 7.84-7.80 (1 H, m),7.76 (2 H, dd, J = 6.20, 3.18 Hz), 7.51 (2 H, dd, J = 6.28, 3.15 Hz), 4.46 (2 H, d, J = 5.76 Hz), 4.37-4.31 (2 H, m), 2.54(4H, s), 2.46 (3 H, s), 2.29 (3 H, s), 1.99 (3 H, s). HRMS (Electrospray): m/z 443.1413 (MH+).

The synthetic route of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; COX, Christopher; RAHEEM, Izzat, T.; SHIPE, William, D.; THEBERGE, Cory, R.; (62 pag.)EP2621276; (2017); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 641571-11-1, 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 641571-11-1 as follows.

4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (100 g, 0.326 mole) and 5-(4-methyl- IH-imidazol-1-yl)-3-(trifluoromethyl)benzenamine (78.75 g, 0.326 mole) were stirred in N-methyl pyrrolidone (700 ml) at 55-60C. Thionyl chloride (83 ml, 0.978 mole) was added and the temperature of the reaction mass was raised to 75C and stirred for 6 hours. The reaction masswas cooled to 40-45C, and water (500 ml) was added. The reaction mass was cooled to 20-25C and acetone (3000 ml) was added. The reaction mass was further stirred for 12 hours. The solid was isolated by filtration and washed with acetone to obtain nilotinib base.Yield :- 200 g

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CIPLA LIMITED; KING, Lawrence; RAO, Dharmaraj Ramachandra; MALHOTRA, Geena; PATHI, Srinivas Laxminarayan; CHINIMILLI, Venugopalarao; GANGRADE, Manish Gopaldas; (21 pag.)WO2016/151304; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, Adding some certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8.

To 100 mg (0.36 mmol) of (S)-5-(4-fluoro-3-(trifluoromethyl)phenyl)-6-methyl-3,6-dihydro- 2H-1,3,4-oxadiazin-2-one (Intermediate 75) and 73 mg of 4-trifluoromethyl imidazole (0.54 mmol) dissolved in 2 mL of DMF was added 235 mg of powdered Cs2C03 (0.72 mmol) and the mixture was heated at 80 Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (2019); 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. 5465-29-2, name is 2-Propylbenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 5465-29-2

[Example 1] (E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (compound 1) (E)-2-(2-Bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (648 mg, 2.00 mmol) obtained in Reference Example B1 and 2-propylbenzimidazole (385 mg, 2.40 mmol) were dissolved in DMA (2 mL), potassium carbonate (553 mg, 4.00 mmol) was added, and the mixture was stirred at room temperature for 14 hr. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=97/3) to give the title compound (compound 1) (778 mg, 96%). ESI-MS m/z: 404 (M + H)+; 1H-NMR (CDCl3, delta): 1.01 (t, J = 7.4 Hz, 3H), 1.85-1.90 (m, 2H), 2.79 (t, J= 7.6 Hz, 2H), 3.06 (br s, 4H), 5.29 (s, 2H), 5.67 (s, 1H), 6.79-6.88 (m, 2H), 7.11-7.35 (m, 7H), 7.43 (dd, J = 7.3, 1.7 Hz, 1H), 7.76 (d, J = 7.3 Hz, 1H).

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 5465-29-2.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4857-06-1, The chemical industry reduces the impact on the environment during synthesis 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

Example 32-5 Synthesis of 1-((2-(trimethylsilyl)ethoxy)methyl)-2-chloro-1H-benzo[d]imidazole General Method XE To a solution of 2-chloro-1H-benzo[d]imidazole (1 g, 6.6 mmol.) in dry DMF (10 mL) was added sodium hydride (60%, 0.26 g, 6.5 mmol.) at room temperature under nitrogen atmosphere. 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl, 1.14 g, 6.8 mmol.) was added dropwise after the solution stirred for 1.5 h. The resulting mixture stirred overnight and then quenched with water and extracted with ethyl acetate (30 mL*3). The combined organic layers was washed with water, dried over sodium sulfate and concentrated to give a residue. The residue was purified by column chromatography to give 1-((2-(trimethylsilyl)ethoxy)methyl)-2-chloro-1H-benzo[d]imidazole (1.13 g, 60.8%).

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-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; InterMune, Inc.; US2009/269305; (2009); 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. 616-47-7, name is 1-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 616-47-7

1-methylimidazole (1 mmol, 82.1 mg),Perfluoro iodobutane (3.1 mmol, 1072 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (2.2 mmol, 246.9 mg) was addedAnd 5mL of toluene, stirring at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).The product 1 was obtained: 2-iodo-1-methylimidazole (white solid, 72 mg, 35%).Product 2: 2,5-diiodo-1-methylimidazole (white solid, 210 mg, 63%)

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; Liaoning University; Liang Fushun; Liu Xia; Han Zhengbo; Su Zhongmin; (10 pag.)CN107501023; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-88-1, 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. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a 0 C solution of 5-bromo-lH-benzimidazole (10.2 mmol) in dichloromethane (30 mL) was dropwise added bis( 1,1 -dimethylethyl) dicarbonate (1 1.2 mmol) and triethylamine (15.2 mmol). The reaction mixture was then stirred at room temperature overnight. The mixture was washed with water (3 x 10 mL) and brine, then dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude product.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; CHAUDHARI, Amita, M.; HALLMAN, Jason; LAUDEMAN, Christopher, P.; MUSSO, David, Lee; PARRISH, Cynthia, A.; WO2011/66211; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-nitrobenzimidazole (1.0 G, 5.6 MMOL) in acetone (50 mL) was added potassium carbonate (1.0 g), followed by alkyl halide (1.2-1. 5 equivalents). The mixture was stirred under nitrogen at rt, then partitioned between ethyl acetate and water after TLC showed completion of the reaction. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a mixture of 1-ALKYL- 5-NITRO-2-METHYLBENZIMIDAZOLE and 1-alkyl-6-nitro-2-methylbenzimidazole, which were dissolved in ethanol-THF (100 mL, 2: 1) and hydrogenated over 5% Pd-C under atmosphere pressure for 8h. After filtration through celte, the filtrate was evaporated to give a yellow solid that was separated with flash chromatography (Methanol-DCM gradient elution). 1-Alkyl-5-aminobenzimidazole and 1-alkyl-6-aminobenzimidazole were obtained as yellow solid or thick syrup.; 5-Amino-1, 2-DIMETHYLBENZIMIDAZOLE (XDS01191B, XDS02082B): Yellow solid, mp 126-127C (LIT. 128C, [23] ). TLC single spot at Rf 0.30 (5% methanol/DCM) ;’H NMR (270 MHz, DMSO): 6 7.08 (1H, d, J = 8.7 Hz, 7-H), 7.65 (1H, d, J = 1.5 Hz, 4-H), 6.50 (1H, dd, J = 8.7, 1.5 Hz, 6-H), 4.63 (2H, broad, NH2), 3.58 (3H, s, NCH3), 2.39 (3H, s, CH3). 6-Amino-1, 2-DIMETHYLBENZIMIDAZOLE (XDS01191A, XDS02082A): Yellow solid. TLC single spot at Rf 0.33 (5% methanol/DCM) ;’H NMR (270 MHz, DMSO): 6 7. 13 (1H, d, J = 8.4 Hz, 4-H), 6.48 (1H, d, J = 2. 0 Hz, 7-H), 6.43 (1H, dd, J = 8.4, 2.0 Hz, 5-H), 4.83 (2H, broad, NH2), 3.53 (3H, s, NCH3), 2.39 (3H, s, CH3).

The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 137049-00-4, 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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of N-[4-methyl-5-(lH-pyrazol-4-yl)-l,3-thiazol-2-yl]acetamide, compound (3) (44 mg; 0.2 mmol; 1 eq.), 1 -methyl- lH-imidazole-4-sulfonyl chloride (36 mg; 0.2 mmol; 1 eq.) and N,N-diisopropylethylamine (0.1 ml; 0.6 mmol; 3 eq.) in DCM (2 ml) was stirred overnight at RT. The reaction mixture was diluted with DCM and washed with water and brine. Organic phase was dried over MgSO4, filtered and evaporated. The resulting crude product was purified by flash chromatography (CHCl3ZMeOH gradient from 100:1 to 50: 50), affording compound (8) as light yellow solid (35 mg; 47.5 %). 1U NMR (DMSO-d6) delta 2.12 (s, 3H), 2.32 (s, 3H), 3.72 (s, 3H), 7.86 (m, IH), 8.06 (s, IH), 8.30 (m, IH), 8.47 (s, IH), 12.11 (br s, IH). M”(ESI): 365.25; M+(ESI): 367.23. HPLC, Rt: 2.31 min (purity: 98.4%).

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-Methyl-1H-imidazole-4-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LABORATOIRES SERONO S.A.; WO2007/82956; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53484-16-5,Some common heterocyclic compound, 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, molecular formula is C8H7BrN2, 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.

3.1. Compound A 2-[4-[(3-methylbenzimidazol-5-yl)amino]phenyl]acetonitrile A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of 6-bromo-1-methyl-benzimidazole (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110° C. for 12 h. The mixture was diluted (DCM), washed (H2O), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound A). MW: 262.3. MS Ms’d: 263.2. NMR: 1H NMR (400 MHz, DMSO-d6): delta=8.13 (1H, s), 7.68 (1H, dd), 7.60 (1H, dd), 7.54 (1H, d), 7.32 (1H, d), 7.24 (1H, t), 6.91 (1H, dd), 3.77 (3H, s), 3.39 (3H, s).

The synthetic route of 53484-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MENET, Christel Jeanne Marie; MAMMOLITI, Oscar; BLANC, Javier; ORSULIC, Mislav; ROSCIC, Maja; US2015/203455; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem