Category: imidazoles-derivatives

These common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-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. COA of Formula: C8H6N2O2

1H-benzimidazole-2-carboxylic acid (183 mg, 1.02 mmol) was dissolved in methylene chloride (20 ml) and DMF (5 ml), reacted with EDCI (195 mg, 1.02 mmol) and HOBt (138 mg, 1.02 mmol) for 20 min, and stirred together with 4b-amino-9b-hydroxy-7-isopropyl-4b,9b-dihydro-5-oxa-indeno[2,1-a]-inden-10-one (250 mg, 0.85 mmol) overnight at room temperature. After extraction with methylene chloride and water, the organic layer was dried over MgSO4 and concentrated in a vacuum. Purification by column chromatography (ethylacetate:n-hexane=1:1) afforded N-(4b-hydroxy-7-isopropyl-10-oxo-9b,10-dihydro-4bH-benzo[d]indeno[1,2-b]furan-9b-yl)-1H-benzo[d]imidazole-2-carboxamide as a white solid (210 mg, 56%). [0822] 1H-NMR (300 MHz, CD3OD) delta 1.19 (d, J=6.9 Hz, 6H, CH3), 2.86 (sep, J=6.9 Hz, 1H, CH), 6.69 (s, 1H, ArH), 6.93 (dd, J=7.9 Hz, 1.2 Hz, 1H, ArH), 7.327.35 (m, 2H, ArH), 7.49 (d, J=7.9 Hz, 1H, ArH), 7.637.64 (m, 4H, ArH), 7.897.91 (m, 2H, ArH).

The synthetic route of 1H-Benzimidazole-2-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN K.U. LEUVEN R & D; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Jung, Young Sik; Lee, Chong Kgo; Kim, Hae Soo; Jeong, Hee Chun; Kim, Pil Ho; Han, Soo Bong; Shin, Jin Soo; Neyts, Johan; Thibaut, Hendrik Jan; US2014/114068; (2014); A1;,
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Synthetic Route of 5805-57-2, These common heterocyclic compound, 5805-57-2, name is (1H-Benzo[d]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.

General procedure: Compound 7 (0.5mmol) and DIPEA (0.7mmol) were mixed in anhydrous DMF (4mL) at 0C. After 45min, HBTU (0.6mmol) followed by the amine partner (8a-s; 0.55mmol) were added and stirring was continued at room temperature for 10-13h. After completion, the reaction mixture was diluted with EtOAc and washed with cold water and followed by brain solution. Then, the organic layer was dried over Na2SO4 and concentrated under the vacuum to obtain the crude product. Then, the residue was purified on flash chromatography using EtOAc/hexane or MeOH/DCM as eluent to obtain the title compounds 9a-s.

The synthetic route of 5805-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Omar, Hany A.; Zaher, Dana M.; Srinivasulu, Vunnam; Hersi, Fatema; Tarazi, Hamadeh; Al-Tel, Taleb H.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 804 – 814;,
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Related Products 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.

The bispyridine ester amine compound (168 mg, 0.83 mmol) in Example 1 and benzoimidazole-2-carboxylic acid (190 mg, 1.17 mmol) were dissolved in DMF (5 m?#8467;), HBTU (402 mg, 1.25 mmol) and triethylamine (0.58 m?#8467;, 4.17 mmol) were added to the solution, and the mixture was stirred at room temperature for 24 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a white solid (247 mg, 86 %) by chromatography (methanol: dichloromethane = 1:30).

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; EP2108649; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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: 1H-Imidazole-4-carbonitrile

(b) 4-acetyl-1H-imidazole 1.42 g (15.3 mmol) 4-cyano-1H-imidazole are combined with 11.2 ml (33.6 mmol) 3n ethereal methyl-magnesium-bromide solution with 25 ml THF in 75 ml THF at 10° C. with cooling in the ice bath and after removal of the ice bath the mixture is stirred for another 2.5 h at ambient temperature. After the addition of another 3.5 ml (10.5 mmol) 3n ethereal methyl-magnesium bromide solution and stirring for 15 min at ambient temperature, 45 ml of 1m sulphuric acid are added and the mixture is stirred for 30 min. After the addition of 20 ml of 10n sodium hydroxide solution the organic phase is separated off, the aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The combined organic phases are dried on magnesium sulphate and evaporated down i. vac. Yield: 48percent C5H6N2O (110.11) Mass spectrum: (M+H)+=111

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; Dahmann, Georg; Gerlach, Kai; Pfau, Roland; Priepke, Henning; Wienen, Wolfgang; Schuler-Metz, Annette; Nar, Herbert; US2008/51578; (2008); A1;,
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Application of 39070-14-9, These common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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 alcohol18(0.50 g, 3.2 mmol) in THF (10 mL) at 0 C was added diisopropylethylamine (0.67 mL, 3.8 mmol) and methanesulfonyl chloride (0.3 mL, 0.38 mmol) and the mixture was stirred for 30 min. EtOAc (20 mL) was added and the solution washed with 1M aqueous HCl (20 mL), dried over MgSO4and solvent removed in vacuo. The crude material was purified by column chromatography (2:1, X4, EtOAc) to yield19(0.51 g, 91%) as a yellow solid, mp 99-100 C (lit. [43] mp 94-96 C). deltaH(CDCl3) 7.19 (1H, s, 4-H), 4.63 (2H, s, CH2), 4.08 (3H, s, CH3). deltaC(CDCl3) 146.4 (C-NO2), 132.9 (C), 128.6 (CH), 34.3 (CH3), 33.9 (CH2). LRMSm/z176.1 (100%, M35+ H), 178.1 (36%, M37+ H). These data are in good agreement with literature values [43].

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dickson, Benjamin D.; Wong, Way Wua; Wilson, William R.; Hay, Michael P.; Molecules; vol. 24; 8; (2019);,
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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

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;,
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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

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

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,
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