Category: imidazoles-derivatives

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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 10111-08-7

Compound 26-2 (0449) To a solution of 2-imidazolecarboxyaldehyde (26-1) (1.92 g, 20 mmol, 1.0 eq) was suspended in methanol (30 mL), NaBH4 (1.52 g, 40 mmol, 2.0 eq) was added portion-wise. The reaction mixture was stirred at room temperature for 1 h under N2. It was quenched with 5 mL of brine. The solvent was removed and the solid was purified with silica gel column chromatography (DCM:MeOH=20:1) to afford a white solid. (1.0 g, Yield: 51%).

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; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 123470-47-3, 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. 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (0.075 mmol), 1,10-phenanthroline (0.15 mmol), 1,8-diiodonaphthalene 1a (0.5 mmol), 1H-benzo[d]imidazole-2-thiols or 2-thiouracils b (0.5 mmol) and base (1.0 mmol). The tube was placed under vacuum for twenty minutes and backfilled with N2, then DMF (2.0 mL) was added via syringe. The reaction mixture was stirred at 100 oC for 24 h. The reaction was monitored by TLC. When b consumed completely, the reaction was stopped and cooled to room temperature, EtOAc (40 mL) was added and the mixture was washed with brine (20 mL × 3). The organic phase was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using petrol/EtOAc (3:1, v:v) as eluent to give c.

The chemical industry reduces the impact on the environment during synthesis 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cui, Jichun; Zhang, Tongxin; Wang, Jianhua; Liu, Dezhi; Wang, Jiaqian; Liu, Jie; Shen, Guodong; Synthetic Communications; vol. 49; 8; (2019); p. 1076 – 1082;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

Scheme A, step a [4S-[4alpha, 7alpha(R*), 12bbeta]]-7-[(5-(4-methoxybenzylthio)-5-oxo-1-(carbo-t-butyloxy)-4,5-dihydrocyclopentimidazole)methylamino]-3,4,6,7,8,12b-hexahydro-6-oxo-1H-[1,4]-oxazino[3,4-a][2]benzazepine Dissolve 4,5-imidazoledicarboxylic acid (31.2 g, 0.2 mol) in ethanol (500 mL) and treat with concentrated sulfuric acid (0.5 mL). Heat to 60 C. for 16 hours, cool and reduce the solvent by 50% in vacuo. Dilute with ethyl ether (500 mL), wash with saturated sodium hydrogen carbonate, then brine. Dry (MgSO4) and evaporate the solvent in vacuo to give 4,5-(dicarboethoxy)imidazole.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merrell Dow Pharmaceuticals, Inc.; US5420271; (1995); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2,Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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.

STAGE 1: 1-((6-chloro-1,3-benzodioxol-5-yl)-methyl)-2,4,5-tribromo-1H-imidazole 25 g of 2,4,5-tribromoimidazole is introduced into 500 ml of dimethylformamide and 4.3 g of sodium hydride is added. Agitation is maintained for 10 minutes at ambient temperature. Next 18.4 g of 6-chloro piperonyl chloride, then 25 g of sodium iodide are added to the reaction medium and agitation is continued for 15 minutes at ambient temperature. The reaction medium is finally poured into 3 litres of water, separated, washed abundantly with water, then successively with 250 ml of ethanol, 250 ml of isopropanol, then finally with 250 ml of isopropyl ether. After drying, 31.5 g of expected product (cream solid) is collected M.p.=225 C. IR CHCl3 (cm-1) Absence of =C–NH

The synthetic route of 2034-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Marion Roussel; US6143774; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-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 128293-62-9, HPLC of Formula: C7H11N3O2

The compound 7 was dissolved in methanol (94.4 ml), mixed with 10 % Pd/C (1.18 g) and stirred for four hours under hydrogen atmosphere. 10% Pd/C was removed from the reaction system with cerite filtration, so that the solvent was distilled out under a reduced pressure. Dimethylformamide (10 ml) was added to the residue and distilled out again under a reduced pressure. The residue was dissolved in dimethylformamide (10 mL) again, and mixed with the compound 8 (5. 9 g, 23.6mmol) (Baird, E. E. ; Dervan, P. B. J. Org. Chem. 1996, 118, 6141-6146), EDC (9.05 g, 47.2 mmol) and dimethylaminopyridine (288 mg, 2. 36 mmol), and stirred for 12 hours at a room temperature. Re-precipitation treatment with chloroform and ethyl acetate gave the compound 9 as white powder (5.9 g, 63%). 1HNMR(DMSO-d6) delta 1.28-1.30 (3H, t, J = 7.1 Hz), 3.85(3H, s), 3.93(3H, s), 3.98(3H, s), 4.25-4.29 (2H, dd, J = 7.1 Hz), 7.03(1H, d, J = 0.7 Hz), 7.22(1H, d, J = 2.0 Hz), 7.38(1H, s), 7.38(1H, s), 7.66(1H, s), 10.35(1H, s), 10.74(1H, s) ; 13CNMR(DMSO-d6) delta 14.3, 35.3, 35.7, 36.5, 60.8, 106.4, 115.6, 119.8, 121.6, 122.2, 126.5, 127.2, 131.0, 138.0, 139.0, 156.3, 158.7, 158.9: Anal. Calcd. for C18H12N4O3·H2O: C, 53.22; H, 4.89; N, 22.57. Found: C, 50.88; H,4.88; N,23.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Japan Science and Technology Agency; EP1719777; (2006); 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

General procedure: Benzimidazole 1 (1mmol) was added to the mixture of AlCl3 or AlBr3 (5.0 mmol) in benzene (3 mL). The reactionmixture was stirred at room temperature for the time as indicated in Table 1. The mixture wasquenched with ice water (50 mL), extracted and worked-up as described above.

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 3012-80-4.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 124750-92-1, name is Losartan 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. Recommanded Product: 124750-92-1

Step B: To the dichloromethane solution of step A product was added triethylamine followed by the addition of triphenylmethyl chloride in methylene chloride and the resulting reaction mixture was stirred at room temperature. The reaction mixture was triturated with water, dried over magnesium sulfate, filtered, concentrated in vacuo, loaded on a silica gel column and eluted with 20-80% acetone / n-hexane to give2-Butyl-4-chloro-1 – {[2 ‘- (2-trityl-2H-tetrazolyl-5) biphenyl-4-] methyl} -1H-imidazole- carboxylic acid.

The synthetic route of Losartan carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Yongtai Technology Co., Ltd.; Lin, Jiaohua; He, Renbao; (22 pag.)CN104447899; (2017); B;,
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. 3543-74-6, name is Ethyl 4-(5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, A new synthetic method of this compound is introduced below., COA of Formula: C18H27N3O4

Example 20: Preparation of crude Bendamustine hydrochloride (form B) [00103] A 5 L bottle was charged with 197 g of phosphorus oxychloride. The contents of the bottle were heated to 50 0C and 150 g of ethyl 4-{5-[bis(2- hydroxycthyl)amino]-l -methyl- lH-benzimidazol-2-yl}butanoatc(“BBOH”) dissolved in 600 ml of dichloromethane was added. Reaction mixture was stirred at 75-85 0C for 4-5 hours. The reaction mixture was then cooled to room temperature and diluted with 450 ml dichloromethane to form a solution. Then the solution was decomposed with 900 ml of 21 % hydrochloric acid and then this reaction mixture was heated at 92 – 96 C for 5-6 h. The resulting solution was then cooled, and its pH was adjusted with 50 % sodium hydroxide to a pH of 1.4 – 1.6 at 0 – 200C. The product crystallized and the mixture was stirred 30 – 60 minutes at 0-100C. The crude Bendamustine was separated by filtration and the filter cake was washed three times with 600 ml of cold dilute hydrochloric acid (1 :20), then three times with 600 ml of cold water, and then three times with 600 ml of ethyl acetate . The filter cake was then dried in wet (relative humidity over 30 %) nitrogen to give 144 g of crude bendamustine hydrochloride.

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; PLUS CHEMICALS SA; TEVA PHARMACEUTICALS USA, INC.; KUCHAR, Martin; KORYTAKOVA, Romana; POSPISILIK, Karel; GAVENDA, Ales; VRASPIR, Pavel; JEGOROV, Alexandr; WO2010/144675; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.

Borylation: A flask is charged with Int 39 (458 mg, 1 mmol, 1 eq.), E^pim (381 mg, 1.5 mmol, 1.5 eq.), dioxane previously degassed with N2 (5 mL), potassium acetate (295 mg, 3 mmol, 3 eq.) and Pd(dppf)Cl2-DCM (82 mg, 0.10 mmol, 0.1 eq.). The mixture is stirred to 100 C overnight, concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on silica gel (eluting with DCM/MeOH 100/0 to 95/5) to afford the expected boronic ester and boronic acid mixture.LCMS: MW (calcd): 505.3; m/z MW (obsd): 506.3 (M+H).LCMS: MW (calcd): 423.1 ; m/z MW (obsd): 424.1 (M+H).; Suzuki coupling: To a stirred solution of boronic ester and boronic acid mixture (51 mg, 0.10 mmol, 1 eq.) and 4-bromo-l -methyl-imidazole (CAS 25676-75-9; 10 pL, 0.10 mmol, 1 eq.) in dioxane (2 mL) is added CS2CO3 (65 mg, 0.20 mmol, 2 eq.), Pd(PPh3)4 (12 mg, 0.01 mmol, 0.1 eq.) in water (0.5 mL). The mixture is heated to 90 C for 1 h then concentrated in vacuo. The residue is diluted in DCM and water. The organic layer is separated and concentrated in vacuo, purified by flash chromatography on Biotage SNAP KP-NH cartridge (eluting with DCM/MeOH 100/0 to 98/2) to afford the expected compound.

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-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; ALVEY, Luke, Jonathan; ANNOOT, Denis, Maurice; BONNATERRE, Florence, Marie-Emilie; BUCHER, Denis; DUTHION, Beranger; JARY, Helene; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; (340 pag.)WO2019/105886; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 124312-73-8, These common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-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.

2-Chloro-6-N-(7i-propyl)amino-[1,3,5]triazin-2-yl)-N,0-dimethyl- hydroxylamine (CD) (1 g, 4.5 mmol), (l-methyl-1H-imidazol-2-yl)methanamine (600 mg, 5.4 mmol) and KaC03 (1.24 g, 9 mmol) in EtOH (50 mL) were heated at 100 C for 16 h. The reaction mixture was filtered, and the volatiles were removed under reduced pressure. The residue was dissolved in EtOAc (100 mL), washed with water (30 mL) and then with a brine solution (30 mL), and lastly dried over Na2S0 . The solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (DCM MeOH=20/l to 8/1) to yield 4-N-(l-N- methylimidazol^-y^-methylamino-e-N-in-pro y amino-tl.S^Itriazin^-yl^NjO- dimethyl-hydroxylamine (CVII, 650 mg, 47%).

Statistics shows that (1-Methyl-1H-imidazol-2-yl)methanamine is playing an increasingly important role. we look forward to future research findings about 124312-73-8.

Reference:
Patent; GALLEON PHARMACEUTICALS, INC.; DAX, Scott, L.; WOODWARD, Richard; PENG, Sean; WO2012/74999; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem