Month: June 2021

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. 4499-07-4, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 4499-07-4

To a solution of benzimidazole ethylene amine dihydrochloride (100 mg, 0.43 mmol), 3,4-dimethylphenoxyacetic acid (77 mg, 0.43 mmol), and BOP reagent (190 mg, 0.43 mmol) in acetonitrile (5 mL) was added triethylamine (0.23 mL, 1.72 mmol). After stirring at room temperature overnight, the solvent was removed under vacuum. The residue was taken up with water and saturated sodium bicarbonate (20 mL), extracted with dichloromethane (30 mL x 2), dried and removed the solvent. The crude mixture was purified by using Gilson HPLC to give white solid 5 as a TFA salt (170 mg) at 93 % yield. MUX LC/MS (10-99%) M+1/Z 324.163 retention time 2.62 min ; 1H NMR (DMSO) 8 2.12 (s, 3H), 8 2.15 (s, 3H), 8 2.99 (t, 2H, J = 5.88 Hz), 8 3.59 (m, 2H), 8 4.40 (s, 2H), 8 6.64 (dd, 1H, J = 2 Hz, 6.5 Hz), 8 6.75 (d, 1H, J = 1.8 Hz), 8 6.98 (8, 1H, J = 6.6 Hz), 8 7.12 (m, 2H), 7.40 (d, 1H, J = 5.76 Hz), 7.53 (m, 1H), 8.30 (t, 1H, J = 4.56 Hz), 12.24 (s, 1H) ; 13C NMR (DMSO) 8 18.4, 8 19. 57, 8 28.58, 8 36.74, 8 67.07, 8 110.8, 8 111.58, 8 116.13, 8 118.12, 8 120.86, 8 121.52, 8 128. 70, 8 130.12, 8 134.21, 8 137.25, 8 143. 24, 8 152. 74, 8 155.73, 8 167. 85.

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; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/42497; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 5-bromo-1-methyl-imidazole (18.8 g, 117 mmol) in dichloromethane (50 mL) was added dropwise ethylmagnesium bromide (3 M in Et2O, 38.9 mL, 117 mmol). After stirring at room temperature for 30 min, the reaction mixture was cooled down to 0C with an ice-brine bath and N-methoxy-N-methylthiophene-3-carboxamide (20.0 g, 117 mmol) was added dropwise. The mixture was stirred for 5.5h at room temperature. The mixture was worked-up by addition of water (400 mL), then acidified with aq. HCI (1 M) until pH = 7. After extraction with dichloromethane (3 x 100 mL), the organic layers were washed with water (2 x 100 mL) then dried over MgSO4 and concentrated in vacuo. Purification of the residue on silica gel afforded (1-methyl-1H-imidazol-5-yl)(2-thienyl)methanone [10.2 g, yield 36% ; HPLC/MS : m/z = 193 (M+H) ; logP(HcooH) = 0.52].

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; BAYER CROPSCIENCE SA; WO2009/130193; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Intermediate 19 (0.1 g, 0.36 mmol),1,1′-thiocarbonyldiimidazole (0.1 g, 0.58 mmol)And triethylamine (0.08 mL)Was dissolved in 30 mL of tetrahydrofuran,60 reflux 5h (TLC detection reaction is completed).After the reaction was completed, the solvent was evaporated under reduced pressure. To the residue was added 30 mL of dichloromethane and a saturated aqueous solution of sodium chloride (3×10 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. (4-cyclopropyl-1-naphthyl) -2-mercapto-1H-imidazo [4,5-b] pyridine (22) as a yellowish solid. Yield 70.9%.

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′-Thiocarbonyldiimidazole, its application will become more common.

Reference:
Patent; Shan Dong University; Lu, Xinyong; Meng, Qing; Zhan, Peng; Fang, Zengjun; Zhao, Tong; Sun, Zhuosen; Sun, Xiukun; (36 pag.)CN106083847; (2016); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 4857-06-1

Sodium hydride (purity 55%)(516 mg, 12.0 mmol) was added to a N,N-dimethylformamide solution (8.0 ml) of 2-chloro-1H-benzimidazole (1.52 g, 10.0 mmol), at 0C, under nitrogen stream, and stirring was carried out for 20 minutes. Methyl iodide (0.750 ml, 12.0 mmol) was further added, and stirring was carried out under room temperature for 2 hours. Water was added to the reaction solution, and the resulting solid substance was collected by filtration to afford 2-chloro-1-methyl-1H-benzimidazole (1.51 g, yield 91%) as a white solid.

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 4857-06-1.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C19H20N4

The compound of formula I (0.62 g, 1 eq) was added to acetonitrile (10 ml) and stirred well. KOH (0.14 g, 1.1 eq) was added slowly, stirred for about 10 minutes, The title compound of Example 10 was added (II, R = COOCH3) (0.5 g, 1 eq) was slowly added, and after stirring for 3-4 hours, TLC After the reaction was complete, 50% ethanol (30 mL) was added directly, The reaction was refluxed for 6 hours. After the TLC test reaction was complete, the organic solvent was recovered under reduced pressure, The remaining solution was added dropwise with hydrochloric acid (1: 1) to pH neutral. There are solid precipitation, filtration, washing, extraction of telmisartan crude, Recrystallization of telmisartan (yield 75.1%), liquid purity greater than 98%.

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; Shanghai Specialization Pharmaceutical Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Wu Mingjun; Li Jianfeng; Chen Weiming; Tian Guanghui; Zhu Fuqiang; Suo Jin; Shen Jingshan; (14 pag.)CN104768936; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2963-77-1, 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. 2963-77-1 name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, 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 solution of stannous chloride 1.6 g, (8.4 mmol) in 30 mL water was added 1.75g (8.4 mmol) of PBA in 30mL ethanol. The reaction mixture was stirred at room temperature for 30 min and then a solution of BPE (2 g, 8.4 mmol in 30 mL water) was added to mixture and heated at 100C for 14 h. The progress of reaction was controlled with TLC (DMF/water: 50/50). At the end of reaction, the reaction mixture was cooled, diluted with ethanol (40 mL), filtered and washed with ethanol and then with DMF to obtain a red precipitate. Yield: 85%, m.p. : 230C; m.f.: C28H26N6SnCl2. UV-vis (DMSO); max (nm): 280, 310, 430. IR (KBr, max, cm-1): 3443 (m), 3338 (m), 3224(m), 1601 (s), 1567 (s), 1497 (s), 1411 (m), 1320 (s), 1236 (s), 1168 (s), 1110 (s), 1069 (s), 849 (s), 744 (m), 607 (m) 498 (m), 434 (m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1H-Benzo[d]imidazol-2-yl)aniline, and friends who are interested can also refer to it.

Reference:
Article; Aroua, Lotfi M.; Asian Journal of Chemistry; vol. 32; 6; (2020); p. 1266 – 1272;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16093-82-6, A common heterocyclic compound, 16093-82-6, name is 1H-Imidazole-2-carboxamide, molecular formula is C4H5N3O, 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 solution of lH-imidazole-2-carboxylic acid amide (360 mg, 3.24 mmol) and phenyl dichlorophosphate (2 mL) was heated at 1700C for 8 min, in a microwaves oven. The reaction mixture was cooled at room temperature and poured into water (50 mL). The solution was cooled at 0C and the pH was adjusted to 11 by addition of NaOH 10 M. Ethyl acetate was added and the phases were separated. The organic layer was dried over sodium sulphate and evaporated in vacuo to provide IH- Imidazole-2-carbonitrile. A solution of lH-imidazole-2-carbonitrile and hydroxylamine (50% sol. in water, 794 muL, 13 mmol) in ethanol (15 mL) was refluxed for 4h. The solvent was removed and the crude N-hydroxy-lH-imidazole-2- carboxamidine was used for the next step without further purification. EPO Yield: quantitative; LCMS (RT): 0.62 min (Method D); MS (ES+) gave m/z: 127.0 (MH+).

The synthetic route of 16093-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2006/123257; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 614-97-1, A common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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.

General procedure: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2, COA of Formula: C5H6N2O2

A suspension of imidazol-1-ylacetic acid, compound of formula 2 (50g, 0. 396mol) and phosphorous acid (48.7g, 0. 594mol) in sulfolan (180ml) was heated to 75 C for 30 min. The mixture was cooled to 35-40 C and phosphorous trichloride (117ml, 1. 346mol) was gradually introduced while maintaining the temperature between 35-45 C. The mixture was heated to 63-67 C for 3 hours, whereby white solid results. It was then cooled to 0- 5’C and quenched by slow addition of water (500ml) at 0-5 C over a period of 1 hour. The resulting clear solution was heated at 100 C for 3 hours, cooled to ambient temperature and charcoalized. Acetone was added to the charcoalized solution. The mixture was then stirred for 4 hours at 20-25 C and the crystallized product was filtered, washed sequentially with chilled water, acetone and dried to obtain zoledronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Imidazol-1-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2005/66188; (2005); 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-1,2-dimethyl-1H-imidazole

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

According to the analysis of related databases, 24134-09-6, 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