Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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 75370-65-9, Application In Synthesis of 4-Amino-1H-benzo[d]imidazol-2(3H)-one

Preparation of 1-(4-fluorobenzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Commercially available p-fluorobenzylamine (0.76 ml, 6.7 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (1.98 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (900 mg, 6 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 420 mg of a white solid. Yield = 23% 1HNMR (DMSO, 200 MHz) delta 4.29 (2H, d, J = 6 Hz), 6.62 (1H, dd, J = 7.6Hz, J’ = 1.2 Hz), 6.80 (2H, m), 6.95 (1H, dd, J = 8.2 Hz, J’ = 1.2 Hz), 7.15 (2H, m), 7.35 (2H, m), 8.23 (1H, bs), 9.96 (1H, bs), 10.59 (1H, bs); [M+1] 301.1 (C15H13FN4O2 requires 300.29).

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-Amino-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16681-56-4, name is 2-Bromo-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 16681-56-4, Quality Control of 2-Bromo-1H-imidazole

In a 10 mL vial was added N-(2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (0.25 g, 0.55 mmol), 2-bromo-1H-imidazole (0.12 g, 0.82 mmol), and Cs2CO3 (0.44 g, 1.36 mmol) in dioxane (5 mL) to give a brown suspension. The reaction mixture was diluted with water (2 mL). Nitrogen was bubbled in for 20 min before Pd(PPh3)4 (0.063 g, 0.05 mmol) was added. The reaction was heated at 110 C for 4 h under microwave conditions. The reaction mixture was concentrated under reduced pressure. The residue was purified by Gilson HPLC (MeCN/0.1% TFA in water). To the purified product was added HCl in Et2O (0.5 mL, 1 mmol). The mixture was concentrated in vacuo to give the HCl salt of the title compound (10 mg, 4.2%). 1H NMR (DMSO-d6) ? 2.31 (s, 3H), 2.36 (s, 3H), 5.32 (s, 2H), 7.18 (d, 2H), 7.39(s, 1H), 7.45 (br s, 1H), 7.61 (s,2H), 7.84 (s, 2H), 7.96 (m, 3H), 8.63 (d,1H), 9.90 (s, 1H), 14.54 (br s, 1H); MS (M+H+) = 399.

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, 2-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Bin; Hird, Alexander W.; Bodnarchuk, Michael S.; Zheng, Xiaolan; Dakin, Les; Su, Qibin; Daly, Kevin; Godin, Robert; Hattersley, Maureen M.; Brassil, Patrick; Redmond, Sean; John Russell, Daniel; Janetka, James W.; Bioorganic and Medicinal Chemistry; vol. 28; 2; (2020);,
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. 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2O

5-methoxybenzimidazole (0.296 g, 2 mmol), 2-(4-Diethylamino-2-hydroxy) benzoylbenzoic acid (0.626 g, 2 mmol) were mixed and addedinto concentrated H2SO4 (3 mL), heated at 100 C for 6 h, and thenslowly cooling to ambient temperature. The resulting mixture wasslowly poured into ice cold water, neutralized by saturated aqueousNaHCO3 followed by extraction with CH2Cl2 (50 mL×3). The organiclayers were collected and dried over Na2SO4, which was subsequentlyevaporated to remove CH2Cl2. Finally, target compound BiF was obtainedas a white powder in yield of 82.0% (0.768 g) through columnchromatography over silica gel eluting with CH2Cl2/CH3OH (v/v=20 :1). M.p.>300 C. ESI-HRMS: calcd. m/z 412.1661 for [M + H]+,found m/z 412.1615 for [M + H]+; 1H NMR (400 MHz, DMSO-d6) delta(ppm) 8.04 (dd, J=6.0 Hz, 2.2 Hz, 1H), 7.65-7.54 (m, 4H), 7.19 (d,J=8.8 Hz, 2H), 6.61 (d, J=8.8 Hz, 1H), 6.48 (d, J=2.4 Hz, 1H), 6.39(dd, J=8.8 Hz, 2.4 Hz, 1H), 3.67 (q, J=7.0 Hz, 4H), 1.18 (t,J=7.0 Hz, 6H). 13 C NMR (100 MHz, DMSO-d6) delta (ppm) 170.36,152.58, 149.65, 140.71, 135.12, 129.84, 128.52, 127.11, 125.28,124.10, 113.10, 108.68, 104.80, 97.57, 84.05, 44.61, 12.65.

According to the analysis of related databases, 4887-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Kun; Han, Defang; Li, Xianglin; Peng, Mengni; Zeng, Xianshun; Jing, Linhai; Qin, Dabin; Dyes and Pigments; vol. 171; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1849-01-0, 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. 1849-01-0 name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-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.

Prepared from 1 -methyl-1,3-dihydro-2H-benzimidazol-2-one (100 mg, 0.6720 mmol), 2-bromo-5-(difluoromethyl-1,3,4-oxadiazole (134.3 mg, 0.67 mmol), potassiumcarbonate (280 mg, 2.02 mmol), copper iodide (12.9 mg, 0.07 mmol) and trans-/V,/Vdimethylcyclohexane-1,2-diamine (0.02 ml_, 0.1400 mmol) in 1,4-dioxane (5 ml.) at 80 C for2 h. Product obtained as a white solid (65 mg, 0.24 mmol, 36%).[00483] 1H NMR (300MHz, DMSO-d6) Shift = 7.88 (d, J=7.6 Hz, 1H), 7.76 – 7.38 (m,25 1 H), 7.38 – 7.32 (m, 2H), 7.31 – 7.22 (m, 1H), 3.41 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan M.; WASZKOWYCZ, Bohdan; HUTTON, Colin P.; WADDELL, Ian D.; HITCHIN, James R.; SMITH, Kate M.; HAMILTON, Niall M.; (265 pag.)WO2016/97749; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17289-26-8, These common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, 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 1-methyl-1H-imidazole-4-carboxaldehyde (0.71 g, 6.45 mmol) in THF (60 mL) was treated with acetic acid (738 jiL, 12.90 mmol) and dimethylamine (2 M in THF, 6.45 mL, 12.90 mmol) and stirred for 2 h. Sodium triacetoxyborohydride (2.74 g,12.90 mmol) was added and the mixture stirred overnight. The reaction was diluted with EtOAc and poured into saturated aqueous NaHCO3. The aqueous phase was concentrated in vacuo and the resultant residue suspended in MeOH-DCM. This was filtered and the filtrate concentrated in vacuo. The crude product was purified using an SCX-2 cartridge and the relevant eluent was concentrated in vacuo to give a residue which was furtherpurified by chromatography eluting from 0-10% (2M NH3 in MeOH) in DCM to afford the title compound as an amber oil (340 mg).?H NMR (300 MHz, DMSO): oe 7.44 (1H, s), 6.91 (1H, s), 3.60 (3H, s), 3.24 (2H, s), 2.11(6H, s).

Statistics shows that 1-Methyl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 17289-26-8.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; SUTTON, Jonathan Mark; CAPALDI, Carmelida; ARMANI, Elisabetta; WO2015/91281; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68892-07-9, name is Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate, 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 68892-07-9, category: imidazoles-derivatives

428 g (2.49 mol) of the commercially available compound (XXIII) were stirred in 2.81 of 3 M aqueous sodium hydroxide solution at 15 C. for 30 mm. Using 6hydrochloride acid, the pH was then adjusted to 1-2 and the precipitate was filtered off with suction. Drying gave 363of the compound (XXIV). 1H-NMR (400 MHz, CD3OD): oe=3.82 (s, 3H),7.58 (s, 1H)

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, Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, REINER; HEIL, MARKUS; JANSEN, JOHANNES-RUDOLF; KUEBBELER, SUSANNE; WILCKE, DAVID; KOEHLER, ADELINE; WILLOT, MATTHIEU; EILMUS, SASCHA; ILG, KERSTIN; MALSAM, OLGA; LOESEL, PETER; PORTZ, DANIELA; ANDERSCH, WOLFRAM; (92 pag.)US2018/7900; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 88a: (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanol To a flask containing 5-bromo-l -methyl- lH-imidazole (650 mg, 4.04 mmol) was added THF (10 mL) and the clear homogeneous solution was stirred at room temperature as z’PrMgCl (2 M in diethylether, 2 mL, 4 mmol) was added. A whitish suspension resulted. The suspension was stirred at room temperature for 30 minutes, then a solution of 4-chloro-2-methoxy-3-(4- (trifluoiOmefhyl)benzyr)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (660 mg, 1.36 mmol, Intermediate 81 : step b) in THF (5 mL) containing LaCl3-LiCl complex (0.5 M solution THF, 5 mL, 2.5 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight at 35 C. After 14 hours, the reaction mixture was quenched with saturated aqueous NH4C1 solution. The aqueous portion was extracted with EtOAc (3 x 40 mL) and the combined organics were washed with brine and dried over MgS04. The brine portion was back-extracted with DCM (3 x 40 mL) and dried over MgS04. The organics were filtered and concentrated to dryness to afford a tan oil. The residue was purified by FCC (2% MeOH-DCM increasing to 10% MeOH) to provide the title compound as an off white solid.lH NMR (500 MHz, CDCI3) delta 8.13 (d, J = 2.0 Hz, 1H), 7.76 (d, J = 8.7 Hz, 1H), 7.50 (d, J = 8.2 Hz, 2H), 7.44 – 7.35 (m, 4H), 7.31 (d, J= 1 1.4 Hz, 1H), 7.05 (d, J= 8.0 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 6.19 (s, 1H), 4.67 (s, 1H), 4.32 (s, 2H), 4.07 (s, 3H), 3.46 (s, 3H), 2.52 (s, 3H), 2.45 – 2.33 (m, 3H); MS (ESI): mass calcd. Chemical Formula: C30H2CIF3N4O?, Exact Mass: 566.2, m/z found 567.1 [M+H]”.(4~Chk>ro~2~niethoxy~3-(4-(irifluQmethyl- lH-im.idazol-5-yl)methanol was purified by chiral SFC (Stationary phase: CHIRALPAK AD-H 5 muetaiota 250 x 20 mm, Mobile phase: 75% C02, 25% EtOH), to give two enantiomers. The first eluting enantiomer was Example 88b and the second eluting enantiomer was Example 88c.

The synthetic route of 5-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

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; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

1-hydroxybenzotriazole monohydrate (16 mg, 0.118 mmol), 3- (ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine (Hydrochloric Acid (1)) (35 mg, 0.183 mmol), and 1-methyl-1H-imidazole-4-carboxylic acid (15 mg, 0.119 mmol) were combined in DMF (0.2 mL) under nitrogen at room temperature and allowed to stir for 40 min. 4-(7-morpholinoquinazolin-5-yl)oxycyclohexanamine (25 mg, 0.0761 mmol) was added, and stirring was continued a further 30 min. Saturated sodium bicarbonate was added, an the mixture was extracted with EtOAc (2x). The combined organics were washed with water (2x), brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography over 4g silica gel using a 0-10% methanol / DCM gradient to yield 1- methyl-N-((1s,4s)-4-((7-morpholinoquinazolin-5-yl)oxy)cyclohexyl)-1H-imidazole-4- carboxamide (6 mg, 17%). 1H NMR (400 MHz, CDCl3) delta 9.44 (s, 1H), 9.10 (s, 1H), 7.51 (d, J = 1.3 Hz, 1H), 7.40 – 7.34 (m, 1H), 7.09 (d, J = 8.4 Hz, 1H), 6.78 (d, J = 1.9 Hz, 1H), 6.57 (d, J = 2.0 Hz, 1H), 4.74 (d, J = 3.9 Hz, 1H), 4.11 (tq, J = 9.9, 6.2, 5.3 Hz, 1H), 3.89 (dd, J = 5.9, 3.9 Hz, 4H), 3.73 (s, 3H), 3.43 – 3.33 (m, 4H), 2.29 – 2.17 (m, 2H), 2.04 – 1.73 (m, 6H). ESI-MS m/z = 433.05 (M+1)+.

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; MAXWELL, John, Patrick; JACKSON, Katrina, Lee; TANG, Qing; MORRIS, Mark, A.; RONKIN, Steven, M.; XU, Jinwang; COTTRELL, Kevin, M.; CHARIFSON, Paul, S.; (280 pag.)WO2019/143678; (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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below., Safety of 6-Aminobenzimidazole

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
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. 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 147403-65-4

Example 17Methyl 2-ethoxy- l -((2′-(5-oxo-4,5-dihydro-l ,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- l H- benzo[£/]imidazole-7-carboxylate of formula la Solid triphosgene (0.12 g, 0.4 mmol) was added to a mixture of methyl 2-ethoxy-l -((2′- ((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)-lH-benzo[i/]imidazole-7-carboxylate (of formula Va; 0.44 g, 1 mmol), THF (10 ml) and triethylamine (0.5 g, 5 mmol) and the mixture was stirred in a closed pressure flask at the temperature of 80 C for 8 hours. After cooling water (20 ml) was added under stirring and, after stirring for 30 minutes, the mixture was acidified with acetic acid. The separated honey-like product was extracted with ethyl acetate, the extract was dried and evaporated to dryness. 0.45 g of a product was obtained, which contained 65.5 % of the compound of formula la according to HPLC. Double crystallization from ethyl acetate yielded 0.28 g (59.5 %) of a product, which contained 95.2 % of the compound of formula la.

According to the analysis of related databases, 147403-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZENTIVA, K.S.; RADL, Stanislav; WO2012/139536; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem