Category: imidazoles-derivatives

Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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. Safety of 2-Imidazolecarboxylic acid

Example 45 lambda/-[6-(1H-lndol-4-yl)-1H-indazol-4-yl]-1H-imidazole-2-carboxamide 1H-lmidazole-2-carboxylic acid (17mg) (available from Maybridge), HATU (63mg) and 6- (1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2/-/-indazol-4-amine (50mg) were dissolved in anhydrous DMF (3ml) and then treated with DIPEA (0.052ml) and stirred at RT for 15h. The mixture was treated with methanol (3ml) and then macroporous-tosic acid resin (170mg; 4.4mmol/g) then stirred for 15h. The mixture was then treated with 0.88 ammonia solution (0.600ml), stirred for 10min, then filtered and solvent blown off under a stream of nitrogen. The crude residue was purified by mass directed preparative HPLC (Method A) to give the title compound. LC/MS R1 0.87min m/z 343 [MH+]. Method B

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, Computed Properties of C3H3IN2

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl2(dppf)(0.041 g, 0.05 mmol) and BnEt3NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

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

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole, A new synthetic method of this compound is introduced below., Formula: C6H6N4

Synthetic example 10:1 , 1 ‘-bis(6-methyl-9-p-tolyl-9H-carbazol-3-y.)-1 H, 1 ,H-2,2i-biimidazole10A mixture of 1W, W-2,2*-biimidazole (890 mg, 6.6 mmol), 3-bromo-6-methyl-9-p-tolyl- 9H-carbazole (6.49 g, 18.6 mmol) and Cs2C03 (7.55 g, 23.2 mmol) in D F (80 mL) was degassed (N2 bubbling, 15 min). Cu20 (380 mg, 2.7 mmol) was added and the mixture was heated (140 C, 96h). The mixture was allowed to cool to room temperature and filtered through Celite washing with CH2CI2. The combined filtrate and washings were concentrated. The mixture was diluted with CH2CI2 and H2O and the organic phase was separated. The aqueous phase was re-extracted (CH2CI2) and the combined organics were washed (saturated aqueous NaCI), dried (MgS04), filtered and concentrated to give a solid residue. The residue was purified by flash chromatography (EtOAc CH2CI2/ eOH 39:60:1 then 37:60:3 then 35:60:5) to give l.r-bisie-methyl-g-p-tolyl-gH-carbazol-S-y -IH.rH^^’-biimidazole (1.42 g, 32%) as a colourless solid. A portion of this material was further purified firstly, by recrystallisation (CH2CI2/toluene/petrol) and then by distillation (sublimation apparatus 270 C, 1CT6 mBar): m.p. 208 – 214 C (DSC); 1H N R (CDCI3, 400 MHz) delta 2.38 (s, 6H), 2.49 (s, 6H), 6.71 (dd, J 1.8, 8.7 Hz, 2H), 7.03 (d, J 8.6 Hz, 2H), 7.05 – 7.20 (m, 8H), 7.23 – 7.40 (m, 12H); 13C NMR (CDCI3, 100 MHz) 5 21.2, 21.3, 109.4, 109.4, 115.7, 119.7, 121.8, 122.4, 123.1, 126.5, 127.8, 129.3, 129.6, 130.4, 134.6, 137.4, 139.6, 139.7; HRMS (El) m/z 671.2916 C46H35 6 [M – Hf* requires 671.2918

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; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; MACDONALD, James Matthew; BOWN, Mark; UENO, Kazunori; WEBER, Karl Peter; O’CONNELL, Jenny Lee; HIRAI, Tadahiko; WO2012/51666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 26663-77-4,Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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 methyl 1H-benzo[d]imidazole-5-carboxylate (0.90 g, 5.1 mmol) in DMF(20 ml) was added NaH (0.25 g, 6.2 mmol), and the reaction mixture was stirred at room temperature for 30 mm. Then (2-(chloromethoxy)ethyl)trimethylsilane (0.94 g, 5.6 mmol) wasadded and the reaction mixture was stirred at room temperature for 2 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (100 mL), washed with H20 (100 mL x 2) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with petroleum ether/EtOAc = 1:1) to afford mixture ofmethyl 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazole-5-carboxylate and methyl 1- ((2-(trimethylsilyl)ethoxy) methyl)- 1 H-benzo [d] imidazole-6-carboxylate as an oil. LC/MS (m/z): 307 (M+H).To a solution of LiA1H4 (0.30 g, 7.8 mmol) in THF (20 ml) was added solution of Step A product (1.2 g, 3.9 mmol) in THF (30 mL) at 0C, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. When TLC showed that the reaction completed, the reaction mixture was quenched with sat. aq. NH4C1 (50 mL) and the mixture was filteredthrough a pad of celite. The filtrate was extracted with EtOAc (100 mL), washed with H20 (100 mL) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford mixture of (1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo [d] imidazol-5-yl) methanol and (1- ((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl)methanol as an oil, which was used in next step without further purification. ?H NMR (CDC13, 400 MHz) oe 8.03 (s, 1H), 8.02(s, 1H), 7.86-7.79 (m, 2H), 7.64 (s, 1H), 7.61-7.55 (m, 1H), 7.43 (d, J= 7.3 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 5.59 (s, 4H), 4.90 (s, 2H), 4.87 (s, 2H), 3.59-3.53 (m, 4H), 0.99-0.91 (m, 4H), 0.00 (s, 9H).To a solution of Step B product (0.3 g, 1.1 mmol) in DCM(10 ml) was added SOC12 (0.8 ml, 10.8 mmol) dropwise at 0C, then the reaction mixture was stirred at room temperature for 3 hours. When TLC showed that the reaction completed, the reaction mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford a mixture of 5-(chloromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d] imidazole and 6-(chloromethyl)- 1 -((2- (trimethylsilyl) ethoxy)methyl)-1H-benzo[d]imidazole as an oil, which was used in next step without further purification. LC/MS (m/z): 297 (M+H).To a solution of Intermediate 2 (0.20 g, 0.65 mmol), Step C product (0.29 g, 0.97 mmol) in acetone (4 ml) and DMF (2 ml) was added K2C03(0.27 g, 1.9 mmol). The reaction mixture was then heated to 60 C and stirred for 6 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (1 OOmL), washed with H20 (100 mL)and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with Petroleum ether/EtOAc = 1:1) to afford a mixture of tert-butyl 2-(4-hydroxy-2-oxo-1-((1-((2- (trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-5 -yl)methyl)- 1,2,5 ,7-tetrahydrofuro [3,4- b]pyridine -3 -carboxamido)acetate and tert-butyl 2-(4-hydroxy-2-oxo- 1 -((1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl) methyl)- 1,2,5,7- tetrahydrofuro [3,4- b]pyridine-3-carboxamido)acetate as a solid. LC/MS (m/z):To a solution of HC1 in dioxane (4M, 20 mL) was added Step D product (140 mg, 0.25 mmol), followed by H20 (5 mL), then the reaction mixture was heated to 90 C and stirred for 4 hours. When LCMS showed that the reaction completed, the reaction mixture was concentrated under reduced pressure to afford crude product as a solid. The crude product was triturated withMTBE (10 mL), and the title compound was collected by suction as a powder. ?H NMR(DMSO-d6, 400 MHz) oe 10.24 (t, J= 4.8 Hz, 1H), 9.48 (s, 1H), 7.80 (d, J= 8.4 Hz, 1H), 7.67 (s,1H), 7.44 (d, J= 8.4 Hz, 1H), 5.24 (br s, 2H), 5.02 (br s, 2H), 4.93 (br s, 2H), 4.06 (d, J= 4.9 Hz,2H). LC/MS (m/z): 385 (M+H). Human HIF-PHD2 IC50: 11.8 nM. 571 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl benzimidazole-5-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (61 pag.)WO2016/49100; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 791595-74-9, name is 5-Bromo-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 791595-74-9, Recommanded Product: 791595-74-9

The corresponding HCl salt of 11 was prepared for biological testing by dissolving 5-bromo-2-aminobenzimidazole (11, 100 mg, 0.47 mmol, 1.0 eq.) in 1,4-dioxane (5 mL) and adding 4.0 M HCl in 1,4-dioxane (589 muL, 2.36 mmol, 5.0 eq.) The resulting precipitate was filtered and dried in vacuo at 50 C. to yield a red crystalline solid. [0219] 1H NMR (300 MHz, DMSO-d6) delta 7.32 (dd, 1H, J=8.4, 0.6 Hz), 7.36 (dd, 1H, J=8.4, 1.7 Hz), 7.55 (dd, 1H, J=1.7, 0.6 Hz), 8.72 (s, 2H), 12.77 (bs, 2H); 13C NMR (75 MHz, DMSO-d6) delta 113.1, 114.1, 114.5, 125.6, 129.1, 131.2, 150.9; ESI-MS: calculated m/z [M+H]+ 211.9818, observed m/z 211.9811.

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; BLACKWELL, Helen; Frei, Reto; Breitbach, Anthony; Lynn, David M.; Broderick, Adam H.; US2013/136782; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1072-63-5,Some common heterocyclic compound, 1072-63-5, name is 1-Vinyl-1H-imidazole, molecular formula is C5H6N2, 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: Allyl chloride (0.10 mol, 7.652 g) was added dropwise over a periodof 30 min to a round-bottomed flask containing 1-benzylimidazole(0.05 mol, 7.910 g) in 20mLAcN under continuous stirring. The mixturewas then stirred for about 1 h and subsequently refluxed at 70 C for24 h till a light brown liquid forms. Excess reactants and solvent wereremoved by rotary evaporation. The crude product was then diluted inan appropriate volume of water and washed three times with 15 mLethyl acetate in a separating funnel. Finally, excess water was removedby rotary evaporation and dried under vacuum at 60 C overnight

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

Reference:
Article; Sidek, Nadiah; A. Manan, Ninie S.; Mohamad, Sharifah; Journal of Molecular Liquids; vol. 240; (2017); p. 794 – 802;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10111-08-7, 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. 10111-08-7 name is Imidazole-2-carboxaldehyde, 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 mixture of acetophenone 7 (0.56g, 3.0mmol) and imidazole-4-carbaldehyde (0.29g, 3.0mmol) in ethanol (25mL) was added 10% sodium hydrate aqueous (5mL), the mixture was stirred for 24h at room temperature [17]. The solution was acidified with 1N HCl and filtered, and the filter cake was recrystallized from ethanol got 8 as white power (0.60g). Yield: 87.4%;

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Imidazole-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Ling; Ge, Yu; Wang, Qing Ming; Zhou, Cheng-He; Bioorganic Chemistry; vol. 88; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 760212-58-6, These common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, 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.

In a one-neck 250 mL flask2.5 g (4.54 mmol) of Intermediate 4, 1.59 g (4.54 mmol) of Int.4, 0.16 g (0.14 mmol) of Pd (PPh3) 4, 1.26 g (9.08 mmol) of K2CO3,50 mL of toluene, 20 mL of ethanol and 10 mL of water were mixed and stirred for 11 hours while heating and refluxing.After the reaction was completed, the solvent was distilled off under reduced pressure, diluted with 50 mL of CHCl3 and filtered using celite.Washed with 100 mL of CHCl3, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain 2.0 g (yield: 64.5%) of 4-42 (WS15-30-305) as a white solid.

The synthetic route of 760212-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lapto Co., Ltd.; MOON, Seong-shik; SEOK, Moon-ki; GO, Byung-soo; KIM, Nam-ho; KWAK, Se-young; HAN, Gab-jong; OH, Eu-gene; (38 pag.)KR2017/103574; (2017); A;,
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. 16681-56-4, name is 2-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 16681-56-4

Example 242 Trans-4-(4-(imidazol-2-yl)-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide Trans-N-((R)-1-(4-fluorophenyl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylsulfonamido)cyclohexanecaboxamide (Intermediate 64, 0.206 mmol), Pd(dppf)Cl2.DCM (19 mg, 0.023 mmol), 2M Na2CO3 (0.57 ml, 1.14 mmol) and 2-bromo-imidazole (17 mg, 0.114 mmol) dissolved in DMF (2 ml) under N2, and the mixture was microwaved at 160 C. for 20 min., after which LCMS indicated that the reaction was complete. The mixture was diluted with DCM and MeOH and filtered through a syringe filter. The filtrate was then passed through a 40+S biotage column with an isocratic gradient of 10% MeOH in EtOAc and the product fractions were combined and concentrated. Crude product was repurified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA) and the product containing fractions were lyophilized to yield the title compound as a white solid (4.2 mg, 3%). MS MH+ 471.1

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BARNES, David; BEBERNITZ, Gregory Raymond; COHEN, Scott Louis; DAMON, Robert Edson; DAY, Robert Francis; JAIN, Monish; KARKI, Rajeshri Ganesh; KIRMAN, Louise Clare; PATEL, Tajesh Jayprakash; RAYMER, Brian Kenneth; SCHUSTER, Herbert Franz; ZHANG, Wei; US2011/136735; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

Weighed 0.680 g (10 mmol) of imidazole,1.240 g (10 mmol) of p-fluorobenzaldehyde and 1.380 g (10 mmol) of anhydrous potassium carbonate were weighed and dissolved in 25 mL of N, N-dimethylformamide and added to a 50 mL four-necked flask equipped with a thermometer and a stirrer The flask. 60 under constant temperature for 20h, cooled to room temperature, poured into 100mL ice water, a yellow solid precipitation, filtration, recrystallization with ethanol, vacuum drying at 50 for 8h, that is, 4 – imidazolyl benzaldehyde.

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; Qilu University of Technology; Xu Ting; Duan Hongdong; Bu Juan; (12 pag.)CN104130192; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem