Month: June 2021

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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methyl-1H-imidazole

To a flask containing 5-bromo-1-methyl-1H-imidazole (345 mg, 2.14 mmol) was added THF (8 mL) and the solution was cooled to 0 C. To this clear homogeneous solution was added isopropylmagnesium chloride-LiCl complex (1.3 M, 2.0 mL, 2.6 mmol) which resulted in a white suspension. The reaction was stirred at 0 C. for 30 min, then a THF (2 mL) solution of N-methoxy-N,2-dimethylthiazole-4-carboxamide (250 mg, 1.34 mmol, Intermediate 38, step a) was introduced and the mixture became more viscous and was allowed to warm to room temperature. After 3 hours the mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (20-40% EtOAc-DCM increasing gradient to 5% MeOH-DCM) provided the title compound as an off-white solid.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 288-32-4, name is 1H-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. SDS of cas: 288-32-4

To a DMF (20 mL) solution of 3-chloro-4-fluorobenzaldehyde (500 mg), potassium carbonate (1.20 g) and imidazole (275 mg) were added one by one, and the reaction solution was agitated at 80 C. overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (elution solvent:ethyl acetate?ethyl acetate_methanol=10:1), and 548 mg of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 10.0 (s, 1H), 8.09 (d, J=2.0 Hz, 1H), 7.91 (dd, J=2.0, 8.0 Hz, 1H), 7.80 (s, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.24-7.27 (m, 2H).

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

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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. Quality Control of Ethyl 3-(1H-imidazol-2-yl)propanoate

To 3-(1H-imidazol-2-yl)propanoic acid ethyl ester [37] (68 mg, 0.40 mmol) in EtOH (0.5 mL) NaOH (2 M, 1.5 mmol, 0.75 mL) was added. The mixture was stirred for 48 h at rt before a pH-value of 1-2 with HCl (0.5 M) was adjusted. After concentration, the crude product was purified using a strong basic ion exchange resin.Colourless crystals; Yield: 61 mg (86%); mp 221 C. IR (KBr) nu cm-1: 3085, 2968, 2727, 1725, 1619, 1507, 1429, 1212, 1188; 500 MHz 1H NMR (CD3OD): delta = 3.21 (m, 2H, CH2COO), 3.30 (m, 2H, CH2CH2COO), 7.41 (s, 2H, CH[4H-Imid.], CH[5H-Imid.]); 126 MHz 13C NMR (CD3OD): delta = 23.6 (CH2CH2COO), 31.0 (CH2CH2COO), 119.0 (CH[4C-Imid.], CH[5C-Imid.]), 147.7 (C[2C-Imid.]), 173.7 (COO); MS (EI, 70 eV): m/z (%) = 140 (16) [M+], 95 (100); MS (CI, CH5+): m/z (%) = 141 (100) [M++1]; HMRS (EI) calcd. for C6H8N2O2: 140.0586; found 140.0583.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

Reference:
Article; Hack, Silke; Woerlein, Babette; Hoefner, Georg; Pabel, Joerg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1483 – 1498;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33016-47-6, name is 1-Trityl-1H-imidazole-4-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 33016-47-6, Recommanded Product: 33016-47-6

Under argon atmosphere, 5.6 ML (2.96 mmol, 1 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise to a solution of 1 g (2.96 mmol) of 1-trityl-1H-imidazol-4-carbaldehyde in 10 ML of THF at 3?6C. The mixture was stirred at 0?5C for 1 hour and 25 minutes. 5.6 ML (2.96 mmol, 1 equivalent) of the solution of ethyl bromozincacetate in tetrahydrofuran obtained in Example 43 was added dropwise at 0?3C. The mixture was stirred at 2?3C for 5 hours and 30 minutes. 5 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 30 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 5 ML of 1N hydrochloric acid, 5 ML of water, 5 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 5 ML (*2) of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. After concentration under reduced pressure, recrystallization with 3 ML of IPE afforded 1.16 g of the desired product (yield 92%).1H NMR (CDCl3): delta 1.22 (3H, t, J=7.1 Hz), 2.83-2.86 (2H, m), 4.13 (2H, q, J=7.1 Hz), 5.09-5.13 (1H, m), 6.78 (1H, s), 7.10-7.15 (6H, m), 7.26-7.39 (10, m).

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-Trityl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1471056; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

To a solution of 4-iodo-1H-imidazole (2.05 g, CAS: 7 1759-89-2) and trityl chloride (4.4 g, CAS: 76-83-5) in DMF (35 mL) was added triethylamine (3.04 mL, CAS: 121-44-8) at 0 C. The reaction mixture was slowly warmed to rt and was stuffed for 48 hours. The reaction mixturewas then poured into H20 (150 mL). The solid was filtered, washed with H20 (60 mL) and dried under reduced pressure. The resulting crude material was purified by flash chromatography using silica gel (EtOAc) to give the title compound as a white solid (4.3 g, 93%). Rf= 0.50 (10% EtOAc/hexane).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, molecular formula is C8H12N2O, 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: 714273-83-3

To a solution of compound 5 (50 g329 mmol) in EtOH (200 mL), NaBD4 (41 g, 979 mmol) was added portion wise under nitrogen. The mixture was stirred for 5 h at -20. The precipitate was removed by filtration. To the filtrate, 2 mol/L aqueous hydrochloric acid (250 ml) was added, and then filtrated. The filtrate was evaporated in vacuo, and then dissolving in water, the pH of the solution was adjusted to 8-9 using saturated potassium carbonate. The crude product was gain by filtration to get 44g compound 6 with a yield at 85%, and was used for next step without further purification. 1H NMR (500 MHz, CDCl3) delta 7.72 (s, 1H), 1.48 (s, 9H). MS (ESI): m/z = 157.22 [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 714273-83-3, its application will become more common.

Reference:
Article; Ding, Zhongpeng; Cheng, Hejuan; Wang, Shixiao; Hou, Yingwei; Zhao, Jianchun; Guan, Huashi; Li, Wenbao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1416 – 1419;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 124312-73-8, These common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, 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.

2-Chloro-6-N-(7i-propyl)amino-[1,3,5]triazin-2-yl)-N,0-dimethyl- hydroxylamine (CD) (1 g, 4.5 mmol), (l-methyl-1H-imidazol-2-yl)methanamine (600 mg, 5.4 mmol) and KaC03 (1.24 g, 9 mmol) in EtOH (50 mL) were heated at 100 C for 16 h. The reaction mixture was filtered, and the volatiles were removed under reduced pressure. The residue was dissolved in EtOAc (100 mL), washed with water (30 mL) and then with a brine solution (30 mL), and lastly dried over Na2S0 . The solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (DCM MeOH=20/l to 8/1) to yield 4-N-(l-N- methylimidazol^-y^-methylamino-e-N-in-pro y amino-tl.S^Itriazin^-yl^NjO- dimethyl-hydroxylamine (CVII, 650 mg, 47%).

Statistics shows that (1-Methyl-1H-imidazol-2-yl)methanamine is playing an increasingly important role. we look forward to future research findings about 124312-73-8.

Reference:
Patent; GALLEON PHARMACEUTICALS, INC.; DAX, Scott, L.; WOODWARD, Richard; PENG, Sean; WO2012/74999; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.

Borylation: A flask is charged with Int 39 (458 mg, 1 mmol, 1 eq.), E^pim (381 mg, 1.5 mmol, 1.5 eq.), dioxane previously degassed with N2 (5 mL), potassium acetate (295 mg, 3 mmol, 3 eq.) and Pd(dppf)Cl2-DCM (82 mg, 0.10 mmol, 0.1 eq.). The mixture is stirred to 100 C overnight, concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on silica gel (eluting with DCM/MeOH 100/0 to 95/5) to afford the expected boronic ester and boronic acid mixture.LCMS: MW (calcd): 505.3; m/z MW (obsd): 506.3 (M+H).LCMS: MW (calcd): 423.1 ; m/z MW (obsd): 424.1 (M+H).; Suzuki coupling: To a stirred solution of boronic ester and boronic acid mixture (51 mg, 0.10 mmol, 1 eq.) and 4-bromo-l -methyl-imidazole (CAS 25676-75-9; 10 pL, 0.10 mmol, 1 eq.) in dioxane (2 mL) is added CS2CO3 (65 mg, 0.20 mmol, 2 eq.), Pd(PPh3)4 (12 mg, 0.01 mmol, 0.1 eq.) in water (0.5 mL). The mixture is heated to 90 C for 1 h then concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on Biotage SNAP KP-NH cartridge (eluting with DCM/MeOH 100/0 to 98/2) to afford the expected compound.

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, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; ALVEY, Luke, Jonathan; ANNOOT, Denis, Maurice; BONNATERRE, Florence, Marie-Emilie; BUCHER, Denis; DUTHION, Beranger; JARY, Helene; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; (340 pag.)WO2019/105886; (2019); 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. 3543-74-6, name is Ethyl 4-(5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, A new synthetic method of this compound is introduced below., COA of Formula: C18H27N3O4

Example 20: Preparation of crude Bendamustine hydrochloride (form B) [00103] A 5 L bottle was charged with 197 g of phosphorus oxychloride. The contents of the bottle were heated to 50 0C and 150 g of ethyl 4-{5-[bis(2- hydroxycthyl)amino]-l -methyl- lH-benzimidazol-2-yl}butanoatc(“BBOH”) dissolved in 600 ml of dichloromethane was added. Reaction mixture was stirred at 75-85 0C for 4-5 hours. The reaction mixture was then cooled to room temperature and diluted with 450 ml dichloromethane to form a solution. Then the solution was decomposed with 900 ml of 21 % hydrochloric acid and then this reaction mixture was heated at 92 – 96 C for 5-6 h. The resulting solution was then cooled, and its pH was adjusted with 50 % sodium hydroxide to a pH of 1.4 – 1.6 at 0 – 200C. The product crystallized and the mixture was stirred 30 – 60 minutes at 0-100C. The crude Bendamustine was separated by filtration and the filter cake was washed three times with 600 ml of cold dilute hydrochloric acid (1 :20), then three times with 600 ml of cold water, and then three times with 600 ml of ethyl acetate . The filter cake was then dried in wet (relative humidity over 30 %) nitrogen to give 144 g of crude bendamustine hydrochloride.

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; PLUS CHEMICALS SA; TEVA PHARMACEUTICALS USA, INC.; KUCHAR, Martin; KORYTAKOVA, Romana; POSPISILIK, Karel; GAVENDA, Ales; VRASPIR, Pavel; JEGOROV, Alexandr; WO2010/144675; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 124750-92-1, name is Losartan carboxylic acid, 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. Recommanded Product: 124750-92-1

Step B: To the dichloromethane solution of step A product was added triethylamine followed by the addition of triphenylmethyl chloride in methylene chloride and the resulting reaction mixture was stirred at room temperature. The reaction mixture was triturated with water, dried over magnesium sulfate, filtered, concentrated in vacuo, loaded on a silica gel column and eluted with 20-80% acetone / n-hexane to give2-Butyl-4-chloro-1 – {[2 ‘- (2-trityl-2H-tetrazolyl-5) biphenyl-4-] methyl} -1H-imidazole- carboxylic acid.

The synthetic route of Losartan carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Yongtai Technology Co., Ltd.; Lin, Jiaohua; He, Renbao; (22 pag.)CN104447899; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem