Tag: M.W=100-200

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. 131020-36-5, name is Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate

Example 11B : 5-Hydroxymethyl-l-methylbenzimidazole A solution of methyl [L-METHYLBENZIMIDAZOLE-5-CARBOXYLATE] (1.6 g, 8.42 mmol) in dry THF (80 mL) was treated with [LIALH4] (1.59 g, 42.1 mmol) and the mixture stirred for 2 hours. 1.5 mL of 5% [NAOH] solution was then added, and the solid which precipitated was filtered through diatomaceous earth. The filtrate was collected and the solvent removed under reduced pressure to give 0. [8] g of the title compound. [C9HLON20] NMR (400 MHz, DMSO-d6): 3.85 (3H, s, NCH3) ; 4.65 (2H, s, [CH20H)] ; 5.25 [(1H,] bs, OH); 7.3 [(1H,] dd, [J =] 1 and [8] Hz, aryl-H); 7.55 [(1H,] d, [J] [=] [8] Hz, aryl-H); 7.65 [(1H,] d, J= 1 Hz, aryl-H); 8.2 [(1H,] s, imidazole-H)

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; AMGEN, INC.; WO2003/99814; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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. Product Details of 4857-06-1

(5) 0.078 mol of 2-chlorobenzimidazole was dissolved in 90 mL of dry N,N-dimethylformamide, and 0.079 mol of 60% sodium hydrogen was added in portions in an ice bath and under a nitrogen atmosphere, followed by an ice bath. Stir for 30 minutes under nitrogen atmosphere, add 0.079 mol of 2-(trimethylsilyl)ethoxymethyl chloride, react at 20C for 16 hours, and turn the reaction solution into a yellow suspension, ice bathUnder cooling, 200 mL of water was slowly added, extracted with ethyl acetate, the organic phases were combined, and after drying, petroleum ether: ethyl acetate was used as eluent at a volume ratio of 10:1 to separate 16 g of white solid compound VII. The yield was 71.93%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4857-06-1, its application will become more common.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; He Xu; Hu Yongzhu; Zhang Chi; Liu Chun; Cui Xilin; (26 pag.)CN107663192; (2018); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17325-26-7

b) 3-(3-Acetoxy-7-chloro-2,2-dimethyl-indan-1 -yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of acetic acid 4-chloro-3-hydroxy-2,2-dimethyl-indan-1-yl ester (1.55 g, 6.1 mmol) in THF (30 mL) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.53 g, 12.2 mmol), and triphenylphosphine (3.2 g, 12.2 mmol). The reaction is cooled to 0 0C and di-f-butyl azodicarboxylate (2.81 g, 12.2 mmol) is added. The reaction is placed at room temperature and permitted to stir for ca. 12 hours and then is heated to 40 0C for 1.5 hours. The reaction mixture is cooled to 0 0C, quenched with 4 N HCI in dioxane (20 ml_, 80 mmol), and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCI. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1 :3) to furnish 3-(3-acetoxy-7-chloro-2,2-dimethyl-indan-1- yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 332.04 (M+H)+.

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 17325-26-7.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8, SDS of cas: 33468-69-8

Example 5: Preparation of Compound 25A microwave vial was charged with Intermediate F (20 mg, 0.044 mmol), 4-(trifluoromethyl)- lH-imidazole (20 mg, 0.15 mmol), CS2CO3 (43.2 mg, 0.133 mmol) and DMA (500 mu). The mixture was heated at 150C under microwave irradiation for 3 h. The mixture was then purified by reverse-phase preparative HPLC (0: 100 to 95 :5 MeCN:water: 0.1% v/v TFA modifier) to afford 1-25 as the TFA salt. ‘H NMR (500 MHz, DMSO-d6) delta = 8.68-8.20 (m, 4H), 5.00 (s, 1H), 4.55-4.38 (m, 1H), 4.22-4.16 (m, 1H), 4.12 (q, 3=1 A, 2H), 3.35-3.24 (m, 1H), 3.22-3.01 (m, 2H), 2.33-2.21 (m, 1H), 2.21-2.09 (m, 1H), 1.30 (d, /=6.9, 5H), 1.24 (t, /=7.2, 3H). MS (EI) Calc’d for C20H24F3N10 [M+H]+, 461; found 461.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; FONG, Kin Chiu; ANTHONY, Neville John; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; LI, Chaomin; TIAN, Yuan; MU, Changwei (Charles); YE, Baijun; SHI, Feng; ZHAO, Xiaoli; FU, Jianmin; WO2015/188369; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 24134-09-6, 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. 24134-09-6 name is 5-Bromo-1,2-dimethyl-1H-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.

A solution of n-BuLi (4.0 mL, 10 mmol, 2.5 M solution in hexane) was slowly added to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (1.77 g, 10.2 mmol) in THF (70 mL) at -78 C. After addition, stirring was continued for an additional 30 minutes and N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (1.76 g, 10.1 mmol, Intermediate 1: step a, Procedure A) dissolved in THF (25 mL) was slowly added. An additional 6 mL of THF was used to complete the quantitative addition. The mixture was stirred at -78 C. for 5 minutes then warmed to room temperature and stirred for 1 hour. The solution was quenched with water and layers were separated. The aqueous layer was extracted with DCM and the combined organic extracts washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified using flash column chromatography (0 to 6% MeOH/DCM) to provide the title compound.

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

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.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-41-1, 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. 3034-41-1 name is 1-Methyl-4-nitroimidazole, 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.

[0280j To a solution of i-methyl-4-nitro-1H-imidazole (500 mg, 3.94 mmol) in MeOH (10 mL) was added Pd/C (50 mg). The mixture was stirred at rt for 16 h under hydrogen atmosphere. Then the mixture was filtered and the filtrate was concentrated in vacuo. The crude product (340 mg. yield: 89%) was used in the next step without further purification. ESI-MS (M+H): 98.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-4-nitroimidazole, and friends who are interested can also refer to it.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2849-93-6,Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, molecular formula is C8H6N2O2, 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 mixture of lH-benzoimidazole-2-carboxylic acid (124 mg, 0.76 mmol) inDMF (5 mL) was added TEA (152 mg, 1.5 mmol) and HATU (347 mg, 0.92 mmol). The reaction mixture was stirred for 5 min and 2-azetidin-3-yl-3 -phenyl-pyridine hydrochloride (100 mg, 0.76 mmol) was added. The reaction mixture was stirred at RT overnight. The mixture was diluted with water (10 mL), and extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL), dried over Na2S04, and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography to give (lH-benzoimidazol-2-yl)-[3-(3-phenyl-pyridin-2-yl)-azetidin-l-yl]-methanone (100 mg, 0.28 mmol, 59% yield) as a light yellow solid

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

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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 934-32-7, Safety of 1H-Benzo[d]imidazol-2-amine

General procedure: A solution of the selected heterocyclic starting material (1.00 mmol) in THF (10 mL) and a solutionof isopentyl nitrite (141 mg, 1.20 mmol) in THF (10 mL) were both pumped at a flow rate of 0.25 mLmin1 with a Vapourtech ?Easy MedChem V3? system, meeting at a PTFE T-piece and the outputflowing through a 10.0 mL coil reactor maintained at 120 C, giving a residence time of 20 min.The pressure of the system was maintained at 7 bar with a back-pressure regulator. For compoundswhere an isolated yield was reported: the output mixture was concentrated under reduced pressureto give an oil (or powder). The oil (or powder) was purified using column chromatography withvarious mixtures of ethyl acetate and hexane as the eluent, or by recrystallisation using methanol, togive isolated compounds that showed no impurities by NMR spectroscopy. For compounds where aconversion was reported (due to volatility of products), the output mixture was carefully concentratedunder a reduced pressure of 100 mbar for 10 min and the conversion was calculated by integration ofproduct peaks to a quantified internal standard (nitrobenzene).

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-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Roeder, Liesa; Nicholls, Alexander J.; Baxendale, Ian R.; Molecules; vol. 24; 10; (2019);,
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. 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, A new synthetic method of this compound is introduced below., Recommanded Product: 360-97-4

(c) 4-f(2-Meth.yl-2-propoxypropyl)amino]–lH-imidazole-5-carboxamide; The reaction mixture of 2-methyl-2-propoxypropanal, which was obtained from Example 2(b), (1.0 g, 8.3 mmol), 5-amino-4-irnidazolecarboxamide (0.5 g, 4.0 mmol), sodium cyanoborohydride (0.25 g, 4.0 mmol) and acetic acid (0.45 mL, 7.9 mmol) in 10 mL of methanol was stirred at ambient temperature for 1 h. The solvent was removed in vacuo. Water (20 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the solvent was removed in vacuo. Purification by ISCO flash (EtOAc:Heptane, gradient elution 1:1 to 100% EtOAc) gave 0.19 g (20 %) of the title compound. 1R NMR (CDCl3) delta ppm 6.98 (s, IH), 6.39 (br s, IH), 3.40 (t, 2H, J=6.7 Hz), 3.14 (d, 2H, J=4.3 Hz), 1.56-1.65 (m, 2H), 1.22 (s, 6H), 0.95 (t, 3H, J=7.5 Hz); MS (ESI) m/z 241 (M+l).

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; ASTRAZENECA AB; WO2007/142576; (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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4ClN3O2

Methanamine (2M in THF, 15 mL) was added to a sealable tube containing 2-chloro-5-nitro- 1 H-benzo[d]imidazole (1 g). The reaction flask was sealed and stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was washed with diethyl ether (15 mL) and dried in vacuo to afford the crude title product as a black tar (600 mg), which was used directly without purification. LCMS m/z 193.06 (M+H)+.

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 5955-72-6.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem