Month: July 2021

Electric Literature of 1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

Example 2Synthesis of [2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-[l-(3- methylimidazol-4-yl)pyrazol-4-yl]methanone.Place [2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-(lH- pyrazol-4-yl)methanone (0.142 g, 0.40 mmoles), 5-bromo-l-methyl-imidazole (89 mg, 0.55 mmoles), cesium carbonate (257 mg, 0.79 mmoles), (1R,2R)- diaminomethylcyclohexane (16 mg, 0.12 mmoles), and copper(I) iodide (7.50 mg, 0.039 mmoles) in a microwave reaction vessel. Add toluene (2 mL) and dimethylformamide (2 mL). The vessel is sealed and purged three times and heated at 110C for 48 hrs. The reaction is allowed to cool to room temperature and is quenched with water (2 mL). Extract three times with ethyl acetate. Dry over sodium sulfate, filter and concentrate under reduced pressure. The residue is purified by reverse phase chromatography to give the title compound (0.078 g, 0.42%). LCMS (m/z): 441.2 (M+l).

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas John; DOTI, Robert Anthony; PFEIFER, Lance Allen; NORMAN, Bryan Hurst; WO2014/168824; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product. Step 5. To a stirred solution oh the A/1482/83/1 cooled to 0 C in THF, a solution of LiOH in water was added dropwise. The mixture was then stirred at room temperature for 2h. UPLC showed complete conversion. The solvent was evaporated under vacuum. The residue was portioned between water and EtOAc, the organic phase was separated and discarded. The water phase was evaporated to give the desired product as the corresponding lithium salt A/1482/84/1. Step 6. To a stirred solution of A/1482/84/1, 4-aminobenzonitrile and TEA in THF 3: 1, HATU was added at room temperature. After stirring for 5h, UPLC showed complete conversion. The solvent was evaporated and the residue partitioned between saturated aqueous NaHC03 and DCM. The organic phase was separated, dried and the solvent evaporated to give an impure product, which was further purified by Si02 column (DCM to DCM:MeOH). The desired product named A/1540/23/1 was recovered as a white solid.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 89830-98-8, These common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-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.

NaH (60 mass%) in minera oi (148 mg, 3.6989 mmo) is added to a soution of 4-cycopropy-1H-imidazoe (200 mg, 1.8495 mmo) in DMF (2 mL) at 0 C under anitrogen atmosphere. The mixture is stirred at 0 C for 15 minutes. 1 ,2-Dibromoethane(0.504 mL 5.5484 mmo) is added at 0 C and the mixture is stirred at room temperaturefor 4 hours under a nitrogen atmosphere. The reaction is quenched by addition of water.The mixture is extracted with EtOAc (3x). The organic phase is washed with saturatedNaC (3x), dried over Na2SO4, fitered, and concentrated to dryness. The residue ispurified by siica ge flash chromatography with 3% MeOH in DCM to give the titecompound as a mixture of 1-(2-bromoethy)-4-cycopropy-imidazoe and 1-(2- bromoethy)-5-cycopropy-imidazoe regioisomers (120 mg, 28.7%) as a cooress oi. ES/IVIS (m/z): 215 (M+1).

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; LIU, Lian Zhu; WANG, Xiaoqing; WILEY, Michael Robert; (34 pag.)WO2019/50794; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Method B, Step 3: (7aS,12a1R)-10-fluoro-3-(3-methoxy-4-(4-methyl-1 H- imidazol-1 -yl)styryl)-6,7,7a,8-tetrahydro-5H-indeno[1 ,2- b][1,2,4]oxadiazolo[4,5-a]pyridine (B3, R9 = 4-(4-Methylimidazol-1-yl), R10 = 3- MeO-Phenyl) B2 (0.24g, 0.63mmole) was dissolved in THF and the reaction was cooled to -78C. n-Butyllithium (2.5ml in Hexane, 0.28ml) was added and the reaction was stirred at -78C for 30 minutes. 3-methoxy-4-(4-methyl-1 H-imidazol-1- yl)benzaldehyde (0.136g, 0.63mmole) in 10 ml THF (Pre-cooled to -78C) was added. The reaction was stirred at -78C for 1 hour, then at room temperature for one hour. THF was removed and the residue was partitioned between 100ml EtOAc and 100ml water. The organic layer was washed with water (2x100ml), dried with Na2SO4 and concentrated. The residue was purified by column (EtOAc/hexane from 25/75 to 100/0 in 45 minutes, 12Og silica). Yield: 0.19g, 68%. 1H NMR (CDCI3400 MHz): 7.73 (s, 1 H), 7.50 (dd, J = 8.1 , 5.12 Hz, 1 H), 7.43 (d, J = 16.8 Hz, 1 H), 7.27 (m, 1 H), 7.18 (d, J = 8.1 Hz, 1 H), 7.13 (s, 1 H), 7.00 (m, 3H), 6.52 (d, J =16.1 Hz, 1 H), 3.90 (s, 3H), 3.71 (m, 1 H), 3.30 (dd, J = 16.1 and 5.9 Hz, 1 H), 2.91 (m, 1 H), 2.64 (m, 1 H), 2.38 (d, J = 16.1 Hz, 1 H), 2.30 (s, 3H), 2.06, (m, 1 H), 1.51 (m, 2H), 1.10 (m, 1 H). MS (M+1 ): 445.2.

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2008/153792; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-16-5, 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. 53484-16-5, name is 6-Bromo-1-methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 13 (210 mg, 0.63 mmol), 5-bromothiazole (156 mg, 0.95 mmol), SPhos (26.0 mg, 0.06 mmol), SPhos-Pd-G2 (45.7 mg, 0.06 mmol) and 2 M aq. Cs2CO3 solution (0.793 ml, 1.59 mmol) in DME (4 mL) was heated at 130 °C for 1 h under microwave irradiation. The mixture was diluted with EtOAc (10 mL), dried over MgSO4, and solvent removed under vacuum. The residue was purified by column chromatography (NH silica gel, eluted with 5?17percent EtOAc/hexane) to yield (E)-tert-butyl 3-(4-(thiazol-5-yl)pyridin-3-yl)acrylate (14a tBu ester, 102 mg, 56percent) as a pale yellow solid. This compound was dissolved in TFA (2.0 ml) and stirred at rt for 2 h. After removal of solvent under reduced pressure, the residue was triturated with EtOAc/hexane (1:1) (3 mL) and the resulting precipitate collected by filtation to yield 14a TFA salt (79 mg, 36percent overall) as a colorless solid

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-1-methyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Fujimoto, Jun; Hirayama, Takaharu; Hirata, Yasuhiro; Hikichi, Yukiko; Murai, Saomi; Hasegawa, Maki; Hasegawa, Yuka; Yonemori, Kazuko; Hata, Akito; Aoyama, Kazunobu; Cary, Douglas R.; Bioorganic and Medicinal Chemistry; vol. 25; 12; (2017); p. 3018 – 3033;,
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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H24N2

(2) Add 50 mL of ethanol to a four-neck round bottom flask.Further added 19.35 g (0.05 mol) of N,N-dimethyl(1-bromopropyl)decyl ammonium bromide, 10.42 g (0.05 mol)N-decylimidazole and1 g of tetrabutylammonium bromide,The mixture was heated to 70 C with stirring, and the reaction was stirred for 36 hours, and then ethanol was distilled off under reduced pressure.The solid was washed three times with chloroform.The filter cake was vacuum dried at 60 C for 5 hours to obtain a crude product;The crude product is recrystallized three times in acetone to obtain the product.1-(N,N-dimethylammonium alkylammonium) propyl-3-hydrazinium imidazolium dibromide,The yield was 85.8%.

The synthetic route of 33529-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University of Light Industry; Yang Xuzhao; Wang Jun; Li Yakun; Ping Dan; Zhang Yingying; Wu Shide; (8 pag.)CN109970657; (2019); 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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Preparation of ( 1 -methyl- l H-benzimidazol- – l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 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; GLENMARK PHARMACEUTICALS S.A.; LINGAM, Prasada, Rao, V., S.; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; BAJPAI, Malini; GULLAPALLI, Srinivas; DAHALE, Dnyaneshwar, Harishchandra; MINDHE, Ajit, Shankar; RATHI, Vijay, Eknath; WO2011/138657; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,1′-Thiocarbonyldiimidazole

A solution of the amine (2.1 g, 8.7 mmol) in anhydrous CH2CI2 (40 ml_) was added dropwise over 2-5 minutes to an ice-NaCI bath cooled solution of 1 , 1 ‘-thiocarbonyldiimidazole (95%, 3.1 g, 17.4 mmol, 2 eq.) in anhydrous CH2CI2 (120 ml_). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1 .5 hours after which time analysis by TLC (5% MeOH in CH2CI2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (13 mL, 91 mmol, 10.5 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (~5 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf Si02 (120 g), 100% CH2CI2? 10% MeOH in CH2CI2) gave the thiourea as an amber oil that solidified to a tacky residue upon standing (2.5 g, 96%).

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DUKE UNIVERSITY; LIEDTKE, Wolfgang; (189 pag.)WO2017/177200; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C45H44N6O3

Example 2; 36.0 g (50.3 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-[2-(trityltetrazol-5-yl)-phenyl]phenyl}-methyl imidazole-5-carboxylate (Va) and 3.0 g (75.4 mmol) of NaOH were suspended in 413 ml dimethylacetamide. The suspension was then stirred at room temperature for 20 h and after that 6.9 g (50.3 mmol) of K2CO3 were added. The mixture was cooled to 0C and solution of 15.4 g (70.4 mmol) 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene in 39 ml of dimethylacetamide were slowly added. The mixture was slowly heated to 50C and stirred at this temperature for 2 h. After esterification was completed, the mixture was cooled to 10 C and poured into a mixture of 625 ml of ethyl acetate and 625 ml of 10 % NaCl, and stirred at 25 C for 15 min. The phases were separated and organic phase was washed 2x with 500 ml of 10 % NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated up to ½ (approximately 270 g) at reduced pressure. To the resulting solution, 80 ml of ethanol and 8.3 ml (100 mmol) of conc. HCl were added and stirred at 24-26C for 3h. To the cooled mixture 600 ml of water was added and pH of the suspension was estimated to 5 by addition of 5 M NaOH. The phases were stirred for 15 min and separated. Water phase was reextracted with 150 ml of ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. 560 ml of ethyl acetate were added and the mixture was evaporated again. After that, 300 ml of ethyl acetate were added and the mixture was cooled to 20 C and stirred for 1h, filtered off and washed with 20 ml of fresh ethyl acetate. The yield of the product (I) was 21 g (75 %).

The synthetic route of 144690-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KRKA, tovarna zdravil, d.d., Novo mesto; EP1816131; (2007); 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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

To a warm solution of [(eta6-p-cymene)RuCl2]2 (30 mg,0.05 mmol) in ethanol (2.5 mL) a warm solution of HL (16 mg,0.1 mmol) in ethanol (2.5 mL) and triethylamine (13.92 mL), wereadded. The mixture was stirred at room temperature for 4 h. Thebright-yellow product was filtered off, washed with ethanol (2 mL),diethyl ether and dried in vacuo. Yield: 30.2 mg, 70.2%. Anal. Calcdfor C18H19ClN2O2Ru, %: C, 50.06; H, 4.43; N, 6.49. Found, %: C, 50.04;H, 4.54; N, 6.52. IR (ATR, cm1): 3069(m), 3025(w), 2961(s),2906(m), 2756(m), 1642(vs), 1591(m), 1529(s), 1475(s), 1328(s),1229(m). 1H NMR (199.97 MHz, DMSO-d6, delta , ppm): 14.04 (s, 1H,NH), 8.11e8.02 (m, 1H, CHL), 7.64e7.56 (m, 1H, CHL), 7.55e7.42 (m,2H, CHL), 6.06 (d, 1H, JHeH 5.8 Hz, CHcymene), 5.97 (d, 1H,JHeH 5.9 Hz, CHcymene), 5.82 (t, 2H, JHeH 5.7 Hz, CHcymene), 2.69(m, 1H, JHeH 6.9 Hz, eCH(CH3)2), 2.17 (s, 3H, eCH3), 1.11 (dd, 6H,JHeH 7.0 and 9.4 Hz, eCH(CH3)2). 13C NMR (50.28 MHz, DMSO-d6,delta, ppm): 18.68 (eCH3), 22.06, 22.11 (eCH(CH3)2), 31.04(eCH(CH3)2), 77.63, 80.25, 80.34, 81.91 (CHcymene), 98.02 (CeCH3),101.04 (CeCH(CH3)2), 114.10, 118.32, 124.49, 125.69 (CHL), 133.97,140.20 (CeCHL), 145.88 (CeCOO), 164.15 (eCOO). ESI-MS (MeOH):m/z 397.049 [M-Cl]+, 353.059 [M-Cl-CO2]+.

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; Panti?, Darko N.; Arancrossed D Signelovi?, Sandra; Radulovi?, Sini?a; Roller, Alexander; Arion, Vladimir B.; Grguri?-?ipka, Sanja; Journal of Organometallic Chemistry; vol. 819; (2016); p. 61 – 68;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem