Tag: M.W=200-300

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., Product Details of 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

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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

c) 1.00 g (2.68 mmol) 6-bromo-2-iodo-dibenzofuran, 1.75 g (5.36 mmol) caesium carbonate, 130 mg (0.67 mmol) copper(l) iodide and 150 mg (1.34 mmol) L-proline are added to 670 mg (3.22 mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 20 ml DMSO under nitrogen. The reaction mixture is stirred for 18 h at 100 C and filtered. THF and toluene are added to the organic phase and the organic phase is washed with water. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product can be used without further purification in step d) (yield = 650 mg (78 %)).1H NMR (400 MHz, CDCI3): delta 8.66 (d, J = 2.2 Hz, 1 H), 8.13-8.19 (m, 2H), 7.96-8.07 (m, 3H), 7.66-7.78 (m, 3H), 7.25-7.45 (m, 5H).

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 28890-99-5.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-03-0,Some common heterocyclic compound, 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, molecular formula is C12H14N2O2, 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 2; Variant 2; Methanesulphonic acid is heated to about 80 C. At a temperature of 75 C. to 85 C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85 C. to 95 C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110 C. to 130 C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160 C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145 C. It is cooled to <100 C. and water is metered into the reaction mixture. 50% sodium hydroxide solution is added at <100 C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100 C.At a temperature of <80 C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40 C. for technical reasons and the product is isolated.Yield: 78-90% of theoryHPLC purity: >99.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2011/190508; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 37067-95-1,Some common heterocyclic compound, 37067-95-1, name is 2-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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.

HL3: 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (1.0 mmol), Pd(OAc)2 (0.05 equiv), PPh3 (0.2 equiv), 1-methyl-2-iodoimidazole (2.5 mmol) were resolved in dimethoxyethane/2M K2CO3 aqueous solution (20 mL, 1:1) under nitrogen atmosphere. The mixture was heated and refluxed for 24 h. After being cooled to room temperature, the reaction mixture was diluted with EtOAc, and poured into a brine solution. The organic layer was separated, and washed with the water, dried, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to obtain the pure product HL3 in 34% yield. 1H NMR (CDCl3): 3.72 (s 6H), 7.12 (d, 2H), 7.47 (t, 1H), 7.48 (d, 2H), 7.56 (s, 1H), 7.72 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Arizona Board of Regents for and on Behalf of Arizona State University; US2011/301351; (2011); 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 53484-16-5 as follows. name: 6-Bromo-1-methyl-1H-benzo[d]imidazole

A mixture containing 6-bromo-1 -methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol),XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mE) was stirred at 1100 C. forapproximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield thedesired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.

According to the analysis of related databases, 53484-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
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. 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C9H6N2O4

General procedure: A mixture of Cd(NO3)2·4H2O (0.0308 g, 0.1 mmol), H3BIDC (0.0412 g, 0.2 mmol) and phen (0.0396 g, 0.2 mmol) with a molar ratio of 1:2:2 were dissolved in the distilled water (5 mL), and stired for 25 min, then set in a Teflon-lined autoclave and heating at 160 C for five days. After cooling to the room temperature, yellow block crystals were obtained. Yield: 28.84 mg (77%, on Cd(II) cations). The products were washed by distilled water and dried in air.

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:
Article; Fan, Rui-Qing; Wang, Li-Yuan; Wang, Ping; Chen, Hong; Sun, Cun-Fa; Yang, Yu-Lin; Su, Qing; Journal of Solid State Chemistry; vol. 196; (2012); p. 332 – 340,9;,
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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C12H14N2O2

Compound IIc (534 mg, 2.45 mmol) was slowly added to polyphosphoric acid (15 mL) heated to 80 & lt; 0 & gt; C, stirred and heated to 150 & lt; 0 & gt; C.Compound IIIb (320 mg, 2.94 mmol) was slowly added to the polyphosphoric acid solution of the former several times, and the mixture was stirred at 150 C for 12 h. After completion of the reaction, the reaction solution was poured into 100 mL of ice water and adjusted to pH 8-10 with concentrated aqueous ammonia. A large amount of precipitate appeared, filtered and the filter cake was washed three times with 5% ethanol solution.After drying the filter cake, the resulting filter cake was purified by chromatography to give about 357 mg (yield 58.7%) of the pale yellow compound IVb.

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; Donghua University; Chen Zhilong; Bao Xiaolu; Zhu Weibo; Wu Zhuo; Yan Yijia; Tang Hesheng; Wang Li; Yu Xinhai; Zhu Zhijia; Xu Yongfen; (15 pag.)CN106749319; (2017); 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

5-Bromo-1,3-dihydrobenzimidazol-2-one (1.30 g, 6.10 mmol), 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol Ester (1.77 g, 6.00 mmol), 1,1′-bisdiphenylphosphinoferrocene palladium dichloride (230 mg,0.314 mmol) and potassium carbonate (2.49 g, 18.0 mmol) were mixed in N,N-dimethylformamide (30 mL).The oxygen was replaced by nitrogen, and then heated to 100 C for 16 hours.The reaction system was diluted with ethyl acetate (300 mL), and the organic phase was washed with water (100 mL×2).The mixture was washed with saturated brine (100 mL × 5) and dried over anhydrous sodium sulfate.The desiccant was removed by filtration, and the solvent was concentrated under reduced pressure.Column chromatography purification (petroleum ether / ethyl acetate / ethanol = 12 / 3 / 1, 3 / 3 / 1),A pale yellow solid (300 mg, yield 17%) was obtained.

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 39513-26-3.

Reference:
Patent; Maidikang (Shanghai) Bio-pharmaceutical Technology Co., Ltd.; Dang Zhu; Ke Lisiting·juecai; Luo Zhen; Wang Liugang; Bao Dan; Qi Tafamingrenqingqiubugongkaixingming; (106 pag.)CN109956931; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 40644-16-4,Some common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5BrN2O, 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.

Step 3: 4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol- 2-one To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in dimethyl sulfoxide (2 ml_) was added potassium acetate (803 g, 10.9 mmol), 1,1′-bis(diphenyl phosphino) ferrocene palladium chloride (PdCI2 (dppf)) (134 mg, 0.16 mmol) and bis(pinacolato) diboron (1.67 g, 6.58 mmol). The mixture was degassed and heated in a microwave oven for 30 minutes at 150 0C. The solvent was filtered through a pad of celite, water (60 ml_) was added and the product was extracted with EtOAc (3 x, 30 ml_). The combined organic extracts were dried over Na2SO4 (sodium sulfate), and the solvent removed to provide crude 4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2-one which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; WYETH; WO2009/111260; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 95470-42-1, 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. 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

(1) Ethyl 2-bromo-4-methyl-1 H-imidazole-5-carboxylate (2.75 g, 11.81 mmol) described in Example 1(1) was dissolved in DMF (20 mE), potassium carbonate (3.26 g, 23.62 mmol) and 2,5-dichlorobenzyl bromide (3.4 g, 14.17 mmol) were added thereto, and the mixture was stirred at 90° C. for 3 hours. Afier the reaction, water (50 mE) was added and the mixture was extracted twice with ethyl acetate (50 mE). The organic layer was washed with saturated aqueous sodium chloride and subsequently dried over sodium sulfate. After concentrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-1 -(2,5- dichlorobenzyl)-4 -methyl-i H-imidazole-5-carboxylate(1.72 g):10160] ?H-NMR (CDC13) oe: 7.34 (1H, d, J=8.8 Hz), 7.20(1H, dd, J=8.8, 2.4 Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s),4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz);10161] ESI-MS mlz=391 (M+H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem