Author: Jessica.F

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

Related Products of 7189-69-7,Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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.

[0118] The following describes a preparation of compound 29. (0215) [0119] To prepare compound 29, a solution of n-butyllithium (2.50 M in hexanes, 84.0 mu., 0.21 mmol, 7.00 equiv) was added to a stirred solution of hexamethyldisilazane (49 mu,, 0.23 mmol, 7.7 equiv) in tetrahydrofuran (5 ml) at 0 C. The reaction mixture was briefly warmed to 23 C then was cooled to 0 C whereupon a solution of 28 (12 mg, 30 muetaiotaomicron, 1.0 equiv) in tetrahydrofuran (2 ml) was added. The resultant mixture was stirred at 0 C for 30 min, then was cooled to -10 C whereupon Nu,Nu’- sulfuryldiimidazole (54 mg, 0.27 mmol, 9.0 equiv) was added. The reaction mixture was warmed to 23 C and stirred at that temperature for 12 h. Excess Nu,Nu-sulfuryldiimidazole was quenched by the addition of methanol (5 ml), and the resultant mixture was concentrated. The residue was partitioned between saturated aqueous bicarbonate solution (20 ml) and dichloromethane (20 ml). The layers were separated and the aqueous phase was extracted with dichloromethane (3 x 25 mL). The combined organic layers were dried over anhydrous sodium sulfate and the dried solution was concentrated. The residue was purified by flash column chromatography (20% ethyl acetate-hexanes) to afford 29 (14 mg, 88%) as a colorless oil. Imidazole 29: TLC: 20% ethyl acetate-hexanes, Rf = 0.33 (UV, CAM). 1H NMR (500 MHz, CDC13) delta: 8.01 (s, 1H), 7.49- 7.47 (m, 3H), 7.39-7.35 (m, 4H), 7.22 (s, 1H), 6.06 (s, 1H), 5.16 (d, J = 10.5 Hz, 1H), 4.57 (dd, J = 1 1.0 Hz, J 4.5 Hz, 1H), 2.57 (s, 3H), 2.27-2.16 (m, 2H), 2.12-2.08 (dd, J = 14.5 Hz, J = 4.5 Hz, 1H), 2.04-1.94 (m, 2H), 1.89-1.83 (m, 1H), 1.76-1.67 (m, 3H), 1.23-122 (m, 1H), 1.19 (s, 3H), 0.95 (d, J = 7.0 Hz, 3H), 0.93 (d, J = 6.5 Hz, 3H), 0.92 (d, J = 7.0 Hz, 3H). 13C NMR (500 MHz, CDC13). delta: 165.2, 156.5, 142.0, 137.1, 131.6, 129.2, 128.5, 126.3, 1 17.9, 116.8, 90.5, 85.3, 81.1, 70.4, 48.8, 46.4, 35.7, 32.5, 31.1, 29.7, 24.0, 22.5, 18.1 , 17.4, 16.8. FTIR (NaCl, thin film), cm”1 2925, 2854, 1718, 1627, 1423, 1203, 1 158. HRMS: ESI [M + H]+ Calcd. for C28H37N206S: 529.2367. Found: 529.2346.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Sulfonyldiimidazole, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; UNIVERSITY OF HAWAII; CHAIN, William J.; BEUTLER, John A.; FASH, David; FIGG, William D.; LI, Zhenwu; PEER, Cody John; RAMOS, Joe William; SULZMAIER, Florian J.; WO2015/120140; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15965-54-5, These common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, 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.

The substances listed in the table which follows are also prepared by the methods given above.

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US6387939; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-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.

The compound (53.8 mg) obtained in Example 1-4 was dissolved in methanol (0.8 ml). Then, the solution was added with trimethyl orthoformate (50 mul), acetic acid (50 mul), and 4-methyl-5-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (28.5 mg) and stirred at room temperature for 10 minutes. Subsequently, sodium cyanoborohydride (24.4 mg) was added, followed by stirring overnight at room temperature. The solvent was distilled off under reduced pressure and then the residue was dissolved in chloroform, followed by washing with 1 mol/l sodium hydroxide and saturated saline solution and drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (33.5 mg) of the subject compound as a white solid. MS(FAB,Pos.)m/z=480[M+H]+1H-NMR(500MHz,DMSO-d6):delta=0.81(6H,t,J=7.3Hz),1.32-1.43(6H,m),1.51(2H,quint.,J=7.1Hz),2.04(3H,br),2.28(4H,t,J=7 .1Hz),2.35(2H,t,J=7.1Hz),3.24(2H,dd,J=6.8,5.9Hz),3.31-3.47(2H,m),3.56(4H,br),6.85(1H,br),7.10(1H,br),7.47(2H,d,J=7 .8Hz),7.51(1H,s),7.78(2H,d,J=8.3Hz),8.40(1H,t,J=5.9Hz).

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

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7757-21-3, name is (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, 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 7757-21-3, Computed Properties of C8H10ClN3

In a 100 mL three-necked flask, NaOH (15 g, 0.38 mol) and 15 mL of water were added, mechanically stirred, and after clearing, III-1 (2.63 g, 14.32 mmol) was added.Tetrabutylammonium bromide (185 mg, 0.57 mmol) was stirred at 25 C for 1 hour, and a solution of 1,2-dibromoethane (5.38 g, 28.64 mmol) dissolved in 50 mL of DMF was added dropwise.After the completion of the dropwise addition, the reaction was carried out at 25 C for 4 hours, and filtered by suction.Inorganic salt, concentrated under reduced pressure to give a white solid.Column chromatography (dichloromethane:methanol:aqueous ammonia = 50:1: 0.05 to 40:1:0.05) was purified to afford product (IV-1) 1.25 g, yield 50.4%.

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, (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; Zhu Qihua; Xu Yungen; Wang Junwei; Li Hui; Zhang Guangxia; Ge Yiran; Guan Zhe; (15 pag.)CN109251204; (2019); A;,
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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1,3-dihydrobenzoimidazol-2-one

EXAMPLE 9 5-(3-Nitro-phenyl)-1,3-dihydro-benzoimidazol-2-one Prepared from 5-bromo-1,3-dihydro-benzoimidazol-2-one and 3-nitro-phenyl boronic acid in the same fashion as that of Example 5. White solid: mp 324-325 C.; 1H-NMR (DMSO-d6) delta 10.8 (s, 2H), 8.4 (m, 1H), 8.15 (d, 1H, J=7.5 Hz), 8.1 (d, 1H, J=7.5 Hz), 7.7 (t, 1H, J=7.5 Hz), 7.35 (d, 1H, J=7.5 Hz), 7.3 (s, 1H), 7.05 (d, 1H), J=7.5 Hz); MS (ES) m/z 254 ([M-H]-, 100%); Anal. Calc. For C13H9N3O3: C, 61.18, H, 3.55, N, 16.46. Found: C, 60.5, H, 3.69 N, 15.53.

According to the analysis of related databases, 39513-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceutical, Inc.; US6423699; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

l,4-Diazabicyclo[2.2.2]octane (21 g, 187.33 mmol) and dimethyl sulfamoyl chloride (18.4 mL, 171.72 mmol) were added to a stirred suspension of lH-imidazole-4- carbaldehyde (15 g, 156.11 mmol) in acetonitrile (300 mL) at 0 C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was concentrated in vacuo and the residue was diluted with water and extracted withEtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 60/40). The desired fractions were collected and concentrated in vacuo to yield 4-formyl-N,N-dimethyl-lH-imidazole-l -sulfonamide (27.2 g, 86 % yield) as a cream solid.

The chemical industry reduces the impact on the environment during synthesis Imidazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53484-18-7, 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. 53484-18-7, name is 1-Methyl-1H-benzo[d]imidazole-6-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of CDI (1.2 equiv) and the proper carboxylic acid in anhydrous solvent under a N2 atmosphere, was stirred at 40-50 C for 3 h. The solution was then cooled at room temperature and 2-amino-5-nitrothiazole and in some cases 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), was added. The mixture was heated at 60 C for 12-18 h, cooled at room temperature and water was added to precipitate the hybrid compounds. The solid was filtered and washed with acetone and water for give the corresponding hybrid compounds.

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-benzo[d]imidazole-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Soria-Arteche, Olivia; Hernandez-Campos, Alicia; Yepez-Mulia, Lilian; Trejo-Soto, Pedro Josue; Hernandez-Luis, Francisco; Gres-Molina, Jorge; Maldonado, Luis A.; Castillo, Rafael; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6838 – 6841;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem