Month: February 2021

68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, 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. Quality Control of 5-Methyl-1H-imidazole-4-carbaldehyde

43[0095] To a solution of O-adamantylhydroxylamine (0.17g, lmmol) and 4-methyl-lH- imidazole-5-carbaldehyde (0.1 Ig, lmmol) in 5ml anhydrous DMSO was added 3mul CH3COOH. The resulting mixture was stirred at ambient temperature overnight. H2O (40ml) was added and the mixture was lyophilized to give white solid. (0.25g, Yield: 96%). 1H-NMR (360 MHz, CDCl3) delta 8.08 (s, IH), 7.55 (s, IH), 2.31 (s, 3H), 2.18 (br s, 3H), 1.88 (br s, 6H), 1.63 (br s, 6H); 13C-NMR (90 MHz, CDCl3) delta 138.5, 138.3, 135.22, 78.16, 41.79, 36.65, 30.84, 12.10; ESI-MS: Calculated for C15H2iN3O (M + H)+ 260.4, Found: 260.2.

The synthetic route of 68282-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; DeGRADO, William, F.; WANG, Jun; WO2011/22191; (2011); 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. 1072-63-5, name is 1-Vinyl-1H-imidazole, A new synthetic method of this compound is introduced below., name: 1-Vinyl-1H-imidazole

(1) Add an appropriate amount of acetonitrile as a solvent to dissolve N-vinylimidazole in a three-necked flask for later use, weigh and configure it as Br (CH2) 6Br:N-vinylimidazole = 1: 2 (molar ratio) mixed product is ready for use; N-vinylimidazole acetonitrile solution is circulated at 82 C under reflux conditions.The above mixture was added dropwise to a three-necked flask and continuously stirred for 24 h.After the reaction, a pale yellow liquid was obtained, and the residual solvent was evaporated under reduced pressure.It was washed several times with ethyl acetate and acetone successively; the product was dried under vacuum to obtain (ViIm) 2C6 (Br) 2.

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; Chengdu Mingdian Shijia Biological Technology Co., Ltd.; Song Hang; (15 pag.)CN110590675; (2019); A;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., Quality Control of 1H-Imidazole

(a) N-Benzylimidazole To a solution of 24 g (1 mol) of sodium hydride in 500 ml of N,N-dimethylformamide, there was added, drop-by-drop, a solution of 68 g (1 mol) of imidazole in 150 ml of N,N-dimethylformamide. The medium was stirred for 2 hours and then 126.6 g (1 mol) of benzyl chloride were added. The solvent was eliminated and the residue was taken up with ethyl acetate and washed with water. The organic phase was dried and concentrated to provide an oil which crystallized when cold. In this manner, N-benzylimidazole was obtained in a yield of 70%.

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; Sanofi; US5017579; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 405173-97-9, 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. 405173-97-9 name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole, 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.

EXAMPLE 230 N-[2-(2-(2-Benzimidazolyl)ethyl)thioethyl]-N’-cyano-N”-methylguanidine Using 2-(2-chloroethyl)benzimidazole, prepared by treating 2-(2-hydroxyethyl)benzimidazole with thionyl chloride, as the starting material in the procedure of Example 17 gives the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Chloroethyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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 flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 10: step d) was added THF (40 ml) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5*50 mL. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 8.21 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.60 (dd, J=8.6, 1.9 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 7.33 (s, 1H), 6.65 (s, 1H), 6.04 (s, 1H), 4.34 (s, 2H), 4.07 (s, 3H), 3.55 (s, 3H). MS (ESI): mass calcd. for C23H19ClF3N3O2, 461.1, m/z found 462.1 [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 1-Methyl-1H-imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 152628-02-9 as follows. HPLC of Formula: C19H20N4

4-Methyl-6-(l -methyl benzimidazol-2-yl)-2-n-propyl lH-benzimidazole (50gms) is suspended in acetone (500 ml), aqueous potassium hydroxide solution (13.8 gms in 31.4 ml of water) is added and mixed for 30 min at temperature of 25 – 3O0C. The mass is cooled, t-Butyl 4″-(bromomethyl)-2-biphenyl-2-carboxylate (50 gms) slowly added over 30 min and maintained the reaction mass at temperature of 0 – 50C for 6 hrs. The solvent is distilled off from the reaction mass at temperature below 5O0C under vacuum. Water (500 ml), Methylene chloride (300 ml) is added to the residue and mixed for about 15 min. pH of the reaction mass is adjusted with hydrochloric acid to 1.8 at temperature of 20 – 250C. Reaction mass is allowed to settle, layers are separated, aqueous layer is extracted with methylene chloride (100 ml). Combined organic layer is washed water (100 ml), treated with charcoal (5 gms) and dried the organic layer over anhydrous sodium sulphate (10 gms). Solvent is distilled off from the dried organic layer at EPO temperature below 50upsilonC finally under vacuum. Acetone (100 ml) is added to the residue,* mixed for about 10 min and solvent is distilled off under vacuum at temperature below5O0C. Acetone (300 ml) is added to the residue, cooled the mass to 3O0C and pH of the mass is adjusted to 2.8 with IPA HCl (about 2 ml). Temperature of reaction mass is raised, maintained for 1 lir at reflux temperature, cooled and maintained for 30 min at 25- 3O0C. Product is filtered, wet cake is washed with acetone (50 ml) and dried the wet cake at temperature of 60 – 7O0C till becomes constant weight.The Dry weight of tert Butyl 4Lambda-[4-Methyl-6-(l-methyl-lH-benzimidazol-2-yl)-2-n- propyl- lH-benzimidazol-l-yl-methyl]biphenyl-2-carboxylate hydrochloride is 73 gms (Yield: 73%). HCl content: 5.85 % w/w

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MATRIX LABORATORIES LIMITED; WO2007/10558; (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. 17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (1-Methyl-1H-imidazol-4-yl)methanol

Step 4: Diisopropylazodicarboxylate 40percent solution in toluene (0.27 mL, 0.51 mmol) was added under stirring to a solution of 5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-ol (100 mg, 0.34 mmol), triphenylphosphine on resin (3 mmol/g) (330 mg, 1 mmol), and 1-methylimidazol-4-yl methanol (60 mg, 0.51 mmol) in THF. The reaction mixture was stirred at ambient temperature overnight. Volatiles were evaporated under vacuum and the residue was purified on 12 g silica gel with 0-20percent methanol in dichloromethane and gave the title compound (40 mg, 0.103 mmol) as yellowish oil. 1H NMR (400 MHz, DMSO-d6) delta 8.07-7.97 (m, 2H), 7.89-7.81 (m, 2H), 7.54 (d, J=8.7 Hz, 1H), 7.50-7.41 (m, 3H), 7.12 (d, J=1.3 Hz, 1H), 5.03 (s, 2H), 3.59 (s, 3H). MS: 390 (MH+).

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 17289-25-7.

Reference:
Patent; Graupe, Michael; Lu, Yafan; Zablocki, Jeff A.; US2015/175560; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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 12; Preparation of NilotinibTo 1 L glass reactor was added the compound of formula 4-methyl-3-{[4-(pyridin-3-yl) pyrimidin-2-yl]amino}benzoic acid of formula X (80.0 g, 0.26 mol), and N-Methyl-pyrrolidone (400 mL). The mixture was heated to 60 C., then SOCl2 (24 mL, 0.33 mol) was added during 15 minutes. The resulted mixture was stirred at 60 C. for 1 h. A compound of formula I (69.2 g, 0.29 mol) was added and the reaction mixture was stirred and heated to 90 C. for 3 h. Water (500 mL) was added and the solution was heated to 80 C. NaOH 47% solution (65 mL) was added until pH 11-12. Then, the suspension was cooled to 40 C. and stirred at this temperature for 2 hours, filtered under reduced pressure at 40 C., and washed with 500 mL H2O to yield a beige solid. This material was slurried in water (1 L) at 40 C. for 1 h, filtered, washed with water (500 mL), and dried under vacuum at 50 C. to obtain 135.25 g of Nilotinib base with 94% yield. (95.8% assay, 99.46% purity).

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39513-26-3, 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. 39513-26-3 name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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 solution of 5-bromo-lH-benzo[d]imidazol-2(3H)-one104 (930 mg) in a mixture of dioxane (47 ml) and 1 M aqueous sodium carbonate (24 ml) was added 5- quinolylboronic acid105 (906 mg). The reaction mixture was purged three times with Argon before adding 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.358 g) and palladium(II) acetate (0.098 g). The reaction mixture was refluxed for 4 hours. Dioxane was removed by evaporation and ethyl acetate was added. The solid obtained was filtered, dissolved in dichloromethane and washed with water. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, eluent: 0 to 5% of methanol in dichloromethane) to afford 5-(2-isopropyl-lH-imidazol-l-yl)-2- nitroaniline (85mg, 27%) as an orange solid. MS (ISP): 247.2 ([M+H]+). The organic layer off and the filter cake was washed with methanol. The filtrate was concentrated in vacuo to 5- quinolin-5-yl-l,3-dihydro-benzoimidazol-2-one as a dark brown solid (949 mg). MS (ISP): 262.2 ([M+H]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,3-dihydrobenzoimidazol-2-one, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Imidazolemethanol hydrochloride

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.

According to the analysis of related databases, 32673-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dinsmore, Christopher J.; Bergman, Jeffrey M.; US2002/52380; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem