Category: imidazoles-derivatives

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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(1H-Imidazol-1-yl)ethanol

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 2.99 g (9.8 mmol) of 1-hexadecylbromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 2.25 g (58%). Mp=52-54 C.IR-spectrum (KBr), cm-1: 3532, 3330, 3134, 3069, 2917, 2850, 1564,1472, 1379, 1165,1071, 873, 792, 720. 1H NMR spectrum, 400 MHz(CDCl3), delta, ppm, J/Hz: 0.88 t (3H, J=6.8), 1.25-1.33m (26 H), 1.91m(2 H), 3.98 t (2H, J=4.91), 4.26 t (2H, J=7.64), 4.53 t (2H, J=7.90),7.31 d (1 H), 7.63 d (1 H), 9.73 s (1 H). ESI MS, m/z: 337.6[M-Br]+.Calculated, %: C21H41N2OBr: C 60.42; H 9.89; N 6.71; Br 19.14; found,%: C 60.23; H 10.12; N 6.45; Br 19.07.

According to the analysis of related databases, 1615-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

EXAMPLE 61: 1-Methyl-2-nitro-5-imidazolaldehyde To a solution of 0.15 g. of 1-methyl-2-nitro-5-hydroxymethylimidazole in 20 ml. of benzene, 0.33 g. of MnO2 is added and the reaction mixture is heated on the steambath for 2 hours. After filtration and evaporation to dryness under vacuum, the crude product is crystallized from ethyl acetate and 0.060 g. (40.5%) of 1-methyl-2-nitro-5-imidazolaldehyde is obtained.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruppo Lepetit S.p.A.; US3954789; (1976); A;,
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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. 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-5-methoxy-1H-benzo[d]imidazole

EXAMPLE 100 0.55 Gram of 2-chloro-5-methoxybenzimidazole, 0.2 g of thiourea and 10 ml of ethanol were mixed together and refluxed for 2 hours. Then, 5 ml of an aqueous solution containing 0.5 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline and 0.3 g of sodium hydroxide was added thereto, and the resulting mixture was refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, to the residue thus obtained was added water, then extracted with chloroform, the chloroform extract was dried with anhydrous magnesium sulfate, and chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to yield 0.5 g of 8-(5-methoxy-2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline in the form of colorless caramel-like substance. NMR (CDCl3) delta: 1.60-2.00 (m, 2H), 2.00-2.40 (m, 2H), 2.27 (s, 3H), 2.72 (t, 2H), 3.78 (s, 3H), 4.78 (t, 1H), 6.77 (dd, 1H), 7.00 (d, 1H), 7.22 (d, 1H), 7.40 (d, 1H), 8.23 (d, 1H).

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; Otsuka Pharmaceutical Co., Ltd.; US4738970; (1988); A;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]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. Product Details of 106429-57-6

2-oxo- 2,3-dihydro-1 /-/-benzoimidazole-5-carboxylic acid methyl ester (3.00 g, 15.6 mmol) and phosphorus oxychloride (30 ml_) were combined and heated to 100 0C for 48 h. The mixture was cooled to 23 0C and concentrated under reduced pressure. The residue was cooled to 0 0C, and cold, saturated aqueous NaHCO3 (60 ml_) was added cautiously. After stirring at 23 0C for 15 min, the mixture was sonicated and the resulting residue was filtered to yield the titled compound (3.13 g, 95%), which was used in the next step without further purification. MS (ESI/CI): mass calcd. for C9H7CIN2O2, 210.02; m/z found, 211.0 [M+H]+.

The synthetic route of Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/134750; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 104619-51-4, 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, This compound has unique chemical properties. The synthetic route is as follows.

Example 28: r4-(5-Amino- H .3.41 oxadiazol-2-yl)-6-ethvnyl-pyridin-3-v?-(2-fluoro-; To a solution of 2-Ethynyl-5- (2-fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (124mg, 0.31 mmol, 1eq) in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (101mg, 0.63mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight, and then poured into water. The solid fomed was isolated by filtration and washed with methanol to afford the product (30 mg). LC/MS (Method A) [5.15min; 422(M+1 )]

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

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., Formula: C7H7N5

A solution of Intermediate 32 (260 mg, 0.470 mmol) in DMSO (2 mL) was treated with di(lH-imidazol-l-yl)methanimine (151 mg, 0.939 mmol) and the mixture was stirred until all of the latter had dissolved. Stirring was then continued for a further 3 h and the mixture was allowed to stand at RT overnight. The mixture was diluted with ethyl acetate and the solution was washed with water. The aqueous was further extracted with ethyl acetate and the combined organics were washed with brine, dried (MgS04) and evaporated. The product was purified on a 5 g Si cartridge eluting with 1 : 1 ethyl acetate in DCM to give the desired product (180 mg). LCMS (Method 4): Rt = 1.55 min, m/z 579.5 [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; CHIESI FARMACEUTICI S.P.A.; ACCETTA, Alessandro; RANCATI, Fabio; CLARK, David Edward; EDWARDS, Christine; (113 pag.)WO2019/238628; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Recommanded Product: 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Synthesis Example 6-1: Synthesis of 2-(4-(N-Boc-N-2-picolylamino methyl) benzoyl)-5-((1-methylbenzimidazol-2-ylmethyl) amino) valerate 1-naphthalenemethylamide (Compound XIII-6) 50.3 mg of the compound synthesised in Synthesis Example 1-4 was dissolved in 1 ml of anhydrous methanol, and then 16.1 mg of 1-methyl-2-formylbenzimidazole was added to the solution and the resultant mixture was stirred for 1.5 hours at room temperature. After the solvent was distilled off, 1 ml of anhydrous methanol and a drop of acetic acid were added to the resultant and the resultant mixture was cooled to 0°C. Subsequently, 14.2 mg of sodium borohydride was added thereto and the resultant mixture was stirred for 0.5 hour at room temperature. The residue obtained by concentrating the reaction solution was purified by means of silica gel column chromatography (2.5 g, chloroform/methanol = 15/1), and 31.3 mg of the above-mentioned compound was obtained as a white solid product. MS(FAB,Pos.):m/z=740[M+1]+ 1H-NMR(500MHz,CDCl3):delta=1.43 and 1.44(9H,2s),1.52-1.63(1H,m), 1.65-1.78(1H,m),1.89-2.01(2H,m),2.68-2.83(2H,m),3.58(3H,s),3. 75(1H,d,J=14.6Hz),3.81(1H,d,J=14.6Hz),4.41and4.44(2H,2s),4.52 and 4.55(2H,2s)4.69-4.75(1H,m),4.85(1H,dd,J=14.6,5.1Hz),4.98 (1H,dd,J=14.6,5.6Hz),7.10-7.35(7H),7.36(1H,d,J=6.6Hz),7.43-7. 51(2H,m),7.52-7.60(1H,m),7.69-7.78(7H,m),7.80-7.83(1H,m),7.99 -8.01 (1H,m), 8.53 (1H,ddd,J=4.9,2.0,1.0Hz).

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; Kureha Chemical Industry Co., Ltd.; EP1389460; (2004); 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. 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 95470-42-1

Ethyl 2-bromo-1-(cyclopropylmethyl)-4-methyl-1H-imidazole-5-carboxylate (EV-AT8650-001)? Step 2 To ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (EV-AT8648-001, 550 mg, 2.36 mmol) in DMF (10 ml), was added potassium carbonate (652 mg, 4.72 mmol) followed by (bromomethyl)cyclopropane (0.25 ml, 2.60 mmol) and the reaction mixture stirred at room temperature for 16h. Saturated aqueous ammonium chloride (150 ml) was added to the reaction mixture and the aqueous layer was extracted with ethyl acetate (2×150 ml). The combined organics were then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (0-100percent ethyl acetate/heptane) to afford 543 mg (80percent) of ethyl 2-bromo-1-(cyclopropylmethyl)-4-methyl-1H-imidazole-5-carboxylate (EV- AT8650-001) as a colourless oil. LCMS (method D): retention time 1.23 min, M/z = 287/289 (M + 1).

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; PADLOCK THERAPEUTICS, INC.; DEVRAJ, Rajesh; KUMARAVEL, Gnanasambandam; ATTON, Holly; BEAUMONT, Edward; GADOULEAU, Elise; GLEAVE, Laura; KERRY, Philip Stephen; LECCI, Cristina; MENICONI, Mirco; MONCK, Nat; PALFREY, Jordan; PAPADOPOULOS, Kostas; TYE, Heather; WOODS, Philip A.; (158 pag.)WO2017/147102; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 71759-89-2, 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. 71759-89-2, name is 5-Iodo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step D 1-Trityl-4-iodoimidazole Trityl chloride (3.8 g, 13.6 mmol) was added to a cooled (0 C.) solution of 4-iodoimidazole (2.25 g, 11.6 mmol) and triethylamine (2 ml, 14.3 mmol) in methylene chloride (25 ml). After stirring for 30 min the reaction mixture was warmed to room temperature and stirred ther for 2 h. The reaction mixture was washed well with water and saturated NaHCO3 then dried (Na2 SO4). Concentration gave the product as a white solid. 1 H NMR (CDCl3) d 6.92 (s, 1 H), 7.08-7.20 (m, 6 H), 7.28-7.40 (m, 10 H).

The synthetic route of 5-Iodo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5932606; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9, 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 2-cyano-4?-(2?-n-propyl-4?-methyl-6?-(1??-methylbenzimidazol-2??-yl)benzimidazol-1?-ylmethyl) biphenyl [0023] In a 2 litre reaction flask 500 ml of methyl isobutyl ketone was added followed by 100 gm of 2-n-propyl-4-methyl-6-(1?-methylbenzimidazol-2?-yl)benzimidazole. The reaction mass was stirred and a solution of 40 gm sodium hydroxide in 300 ml water was added. To this solution, 10 gm tetra butyl ammonium hydrogen sulphate and 80 gm of 4-chloromethyl-2?-cyanobiphenyl was added. The reaction mass was warmed to 80 C. and maintained for 4 hours at 80 to 85 C. [0024] The completion of the reaction was monitored by TLC using mobile phase chloroform: methanol (9:1). After completion of the reaction, the mass was cooled to 20 C., maintained 3 hours at 15 to 20 C. The product which precipitated out was filtered, washed with methyl isobutyl ketone, followed by water to yield 126 gm of 2-cyano-4?-(2?-n-propyl-4?-methyl-6?-(1??-methylbenzimidazol-2??-yl)benzimidazol-1?-ylmethyl) biphenyl, melting at 196-198 C. [0025] C 80.53%, H 5.70%, N 14.20%; m/z=496.64 1H NMR DMSO d6 400 Mhz: delta ppm 0.96-0.99 (t, 3H) 1.75-1.84 (m, 2H) 2.62 (s, 3H) 2.89-2.93 (t, 2H) 3.80 (s, 3H) 5.67 (s, 2H) 7.18-7.92 (m, 14H)

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, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amarnath, U; Suryakiran, U; US2015/197495; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem