Month: January 2021

Reference of 41716-18-1, The chemical industry reduces the impact on the environment during synthesis 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of intermediate 12-g (610 mg, 1.17 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (177 mg, 1.40 mmol), HATU (624 mg, 1.64 mmol) and DIPEA (816 uL, 4.69 mmol) and the reaction mixture was stirred at 0¡ã C. for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 13-a as a white foam.

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-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-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 760212-58-6, HPLC of Formula: C19H13BrN2

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.2 g (3.2 mmol) of 9,10-diphenylanthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1. 6 g of a greenish white solid (90% yield) . Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 598 with respect to a molecular weight of 598.24.

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; IDEMITSU KOSAN CO., LTD.; EP1734038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 705-09-9, A common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

A mixture of the material so obtained, 2-difluoromethyl-lH’-benzimidazole (0.435 g), potassium carbonate (1.36 g) and DMF (15 ml) was stirred under nitrogen and heated to 1100C for 24 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. There was thus obtained 4-chloro-2-(2-difluoromethylbenzimidazol-l-yl)- 6-[(3iS)-3-methylmorpholin-4-yl]pyrimidine (0.76 g) which was used without further purification.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32086; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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. name: 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole

Preparation of Compound F[186] Compound F-2 (38.6g, 110mmol), potassium acetate (32.4g, 330mmol), bis(pinacolato)diboron (36.5g, 143mmol), 1,4-dioxane (390mL), and PdCl2(dppf) (1.8g, 2mmol) were mixed and stirred at 80 for 18 hours, and then cooled at room temperature. Water (400mL) was added to the reactant and stirred. After stirring, an organic layer was extracted by adding saturated sodium chloride aqueous solution and ethyl acetate, dried over magnesium sulfate, and treated with activated charcoal, followed by filtering with celite. A solid prepared by concentrating the filtrate under reduced pressure was re-crystallized, thereby obtaining Compound F (36g, 82%).[187] 1H NMR (CDCl3) d 7.92(d, 1H), 7.76(d, 2H), 7.59(d, 2H), 7.56-7.45(m, 3H), 7.41-7.29(m, 4H), 7.27(s, 1H), 1.35(s, 12H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2620-76-0, its application will become more common.

Reference:
Patent; ALPHA CHEM CO., LTD.; NAM, Hyun Goog; LIM, Dae Won; KIM, Jae Yong; PARK, Sang Mi; JANG, Seung Hee; LEE, Sang Youn; HAM, Ju Seok; CHO, Kyu Oh; KIM, Hyun Don; WO2013/180376; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, 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 95470-42-1, Recommanded Product: Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

(2) Ethyl 2-bromo-4-methyl-i H-imidazole-5-carboxylate (5lene (4.56 g, 25.8 nmol) were added thereto, and the mixmre g, 21.45 mmol) was dissolved in DMF (40 mE), potassium carbonate (5.93 g, 42.9 mmol) and 1 -(chloromethyl)naphthaNwas stirred at 80¡ã C. for 2 hours. After the reaction, water wasThe organic layer was washed with samrated aqueous sodiumadded and the mixture was extracted twice with ethyl acetate.chloride and dried over anhydrous sodium sulfate. Afier con-centrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-4-methyl-1 – (naphthalen-1 -ylmethyl)-i H-imidazole-5-carboxylate (3.2510129] ?H-NMR (CDC13) oe: 8.01 (1H, d, J=8.3 Hz), 7.91(1H, d, J=7.8 Hz), 7.77 (1H, d, J 8.3 Hz), 7.63-7.53 (2H, m),7.33 (1H, t, J=7.6 Hz), 6.43 (1H, dd, J=7.3, 1.0Hz), 6.07 (2H,s), 4.13 (2H, q, J=7.i Hz), 2.58 (3H, s), 1.11 (3H, t, J=7.i Hz);10130] ESI-MS mlz=373 (M+H).

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; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 30148-21-1,Some common heterocyclic compound, 30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H10N2O2, 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.

IM-1 (1.8 g) was dissolved in concentrated H2S04 (5 mL) and cooled to 0C. Nitric acid (90%, 5 mL) was slowly added and the solution warmed to room temperature and then refluxed at-20C for 1.5 hr. The reaction was quenched by pouring onto ice (50 mL). The resulting blue solution was extracted with DCM, dried over sodium sulphate, and evaporated under vacuum to yield a tanned and oily product. The residue was precipitated with CCL4 : EtOH (1 : 1, 5 mL) to yield the product as white crystals. Yield (1.0543 g, 45%). H NMR (DMSO): 6 8.61 (s, 1H), 4.33 (q, 2H, J=6. 4 Hz), 3.97 (s, 3H), 1.29 (t, 3H, J=6. 0 HZ). 13C (DMSO) : 158.2, 145.4, 135.3, 127.4, 62.2, 37.3, 14.5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1-methyl-1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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 939-70-8, 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. 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 1-(1H-benzo [d] imidazol-2-yl)ethanone (2) (0.01 mol) in ethanol (60 ml),benzaldehyde (0.01 mol) and a few drops of glacialacetic acid were added and the mixture refluxed for10 hr. It was then cooled concentrated and pouredinto crushed ice and filtered. The solid thus obtainedwas purified by recrystallizaton from ethanol.

The chemical industry reduces the impact on the environment during synthesis 1-(1H-Benzo[d]imidazol-2-yl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bhaskar; Bharahmeswari; Indian Journal of Heterocyclic Chemistry; vol. 23; 2; (2013); p. 207 – 212;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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. SDS of cas: 26663-77-4

Methyl lH-benzo[d]imidazole-5-carboxylaie (528 mg, 3 mrnol) in lOmL of DMF was added NaH (160 mg, 6 mmol) at 0C under 2, then the mixture was stirred at (TC for 30 min, then a solution of tert-butyl 4′-(bromomethyl)biphenyl- 2-carboxylate (1.09 g, 3.15 mmol) in DMF (5 mL) was added dropwise at 0C to the reaction mixture, then the mixture was stirred at RTovernight. The mixture was poured into 50 mL of water. The mixtitre was extracted with EtOAc (30 ml_x3) and washed with water (20 mL) and brine (20mL), dried over Na2S04, filtered, and concentrated. The crude product was purified with Combiflash (hexane/EtOAc = 2/1, silica gel) to obtain the titled compound 1. ? NMR (CHLOROFORM-d) delta 8.57 (s, 1H), 8.13 (s, 3H), 7.98 – 8.06 (m, 5H), 7.75 – 7.82 (m, 2H), 7.46 – 7.53 (m, 2H), 7.37 – 7.44 (m, 4H), 7.22 – 7.35 (m, 14H), 5.49 (s, 2H), 5.46 (s, 3H), 3.96 (s, M l ). 3.95 (s, 3H), 1.19 (d, J – 9.7 Hz, 22H); Step B: l -((2′-(tert-butoxycarbonyl)-[l , i ‘~biphenyl]~4-yl)raetliyl)- lH- benzo[d]imidazole-5-carboxy1ic acid, 1 -((2’-(tert-butoxycarbonyl)- [ 1 , Gamma- biphenyl]-4-yl)methyl)- lH-benzo[d]imidazole-6-carboxylic acid The mixture 1 (from Step A) (300 mg, 0.68 mmol) and LiOH (83 mg, 2.04 mmol) in methanol (5 mL) and H?0 (2 mL) was stirred at RT for 18 h. Methanol was removed under the reduced pressure, then PH was adjusted to 6 with IN HCl. A gradual formation of precipitate was observed and filtered. The filter cake was washed by water (10 mL). The residue was separated and purified with Prep-TLC (PE/EtOAc = 112, silica gel) to give the titled compound 2 and 3. 2 ? NMR (CHLOROFORM-d) : 8.26 (s, 2H), 7.75 7.84 (m, 1H), 7.47 ¡¤ 7.54 (m, l H), 7.38 – 7.44 (m, 1 H), 7.29 – 7.36 (m, 5H), 5.52 (s, 2H), 1 .19 (s, 9H) 3 T NMR (CHLOROFORM-d) delta: 8.76 (s, 1H), 8.31 fs, 1H), 7.77 – 7.85 (m, 1H), 7.38 – 7.54 (m, 4H), 7.33 (t, J = 8.2 Hz, 4H), 5.49 (s, 2H), 1.21 (s, 9H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26663-77-4, its application will become more common.

Reference:
Patent; RIPKA, Amy S.; SAUNDERS, Jeffrey O.; KAMENECKA, Theodore Mark; GRIFFIN, Patrick R.; WO2013/78240; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route 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.

Example 8 3-(1H-benzimidazol-2-methylene)-5-(4-methylphenylaminosulfo)-2-indolone (Indo 8) 0.15 g (0.5 mmol) 5-(4-methylphenylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazoyl-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.18 g pale yellow solid, with a yield of 83.7percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta(ppm): delta13.82 (s, 1H), 11.70 (s, 1H), 10.06 (s, 1H), 8.32 (s, 1H), 8.06 (s, 1H), 7.83 (d, 1H, J=8.0 Hz), 7.79 (d, 1H, J=8.4 Hz), 7.67 (dd, 1H, J=16.8 Hz), 7.38 (t, 1H), 7.31 (t, 1H), 7.30 (d, 2H, J=13.6 Hz), 7.06 (d, 2H, J=8.4 Hz), 7.03 (s, 4H), 2.17 (s, 3H). ESI-MS m/z: 429[M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(4-methylphenylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is 4-methylphenylaminosulfo, R2 is hydrogen.

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; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem