Category: imidazoles-derivatives

Application of 1231930-33-8, These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-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.

Under nitrogen protection, 24 palladium acetate (28 mg) and 25 tricyclohexylphosphine (54.3 mg) was added into the solution of 26 6-bromo-4-fluoro-1-isopropyl-2-methyl-H-benzo[d]imidazole (300 mg, 1.10 mmol), 27 bis(pinacolato)diboron (422 mg, 1.70 mmol) and 28 potassium acetate (326 mg, 3.3 mmol) in anhydrous 29 dimethyl sulfoxide (DMSO, 5 mL), and the reaction was carried out at 100 C. under nitrogen protection for 2 hours. After cooling to room temperature, the reaction was filtered on Celite, the filter cake was washed with ethyl acetate, the filtrate was washed with brine, dried over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=3:1), to affard 260 mg of a pale yellow solid. Yield: 74.3%. LC-MS(APCI): m/z=319.3 (M+1).

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen TargetRx, Inc.; Wang, Yihan; Ren, Xingye; Jin, Jian; Li, Huanyin; Ai, Yixin; (162 pag.)US2019/152954; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17289-26-8, 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a 0.2 M solution of intermediate (l-36a) in THF was added 1.1 eq 1 -methyl- 1 H-imidazole-4-carbaldehyde (Ryan Scientific, Inc., Mt. Pleasant, SC), and this solution was then cooled to 0 C. To this solution was added 0.5 equivalents of potassium t- butoxide as a 1 M solution in THF, and the reaction was allowed to slowly warm to RT. After 18h the solution was acidified with 1 N HCI, brine was added, and extracting three times with ethyl acetate. The resulting organic layers were then combined, dried over sodium sulfate and concentrated to afford crude (l-36b). This material was taken forward crude.

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, 1-Methyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5955-72-6, These common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-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.

[0635] A mixture of 2-chloro-5-nitro-benzimidazole (985 mg, 5.0 mmole) and 1-(3-aminopropyl)-imidazole (1.8 mL, 3 eq) in toluene (15 mL) was heated at reflux for 5 hr. The reaction was partitioned between EtOAc and brine to give a precipitate that was collected by filtration. Flash chromatography of this material (silica gel; stepwise gradient elution with mixtures of DCM containing 1, 2, 3, . . . 10% MeOH) afforded 2-[3-[imidazo-1-yl]-propylamino]-5-nitro-benzimidazole (550 mg) as a solid. This material was combined with 10% Pd on charcoal (500 mg), suspended in EtOH, and stirred under a hydrogen atmosphere (balloon) overnight. Removal of the catalyst by filtration and the solvent under reduced pressure left the crude 5-amino-2-[3-imidazo-1-ylpropylamino]-benzimidazole as a solid. A portion of this material (77 mg, 0.30 mmole) was added to a mixture of 319A (99 mg, 1.0 eq), an aqueous solution of HCl (0.60 mL, 1.0 M, 2 eq) and n-BuOH (1.5 mL). This was heated in a sealed vial at 120 C. for 20 hr. After cooling to RT, 572 (HPLC retention time (YMC ODS S7 3×50 mm): 1.20 min) was isolated by preparative HPLC.

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

Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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 20485-43-2, Formula: C5H6N2O2

To a solution of N4-(3-aminopropyl)-7-(lH-pyrazol-5-yl)quinoline-2,4-diamine, 3 HC1 (30 mg, 0.077 mmol) and 1 -methyl- lH-imidazole-2-carboxy lie acid (19.32 mg, 0.153 mmol) and triethylamine (0.213 mL, 1.532 mmol) in DMF (1 mL) was added T3P (50% in DMF) (97 mg, 0.153 mmol). After stirring the reaction at room temperature overnight the reaction was concentrated under high vacuum. The reaction was diluted with 1 ml of a mixture of 1: 1 DMF: acetic acid and filtered through a syringe filter and purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 200 mm x 19 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95 :5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: a 5-minute hold at 0% B, 0-33% B over 25 minutes, then a 5-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to give N-(3-((2-amino-7-(lH-pyrazol-5-yl)quinolin-4- yl)ainino)propyl)-l-methyl-lH-imidazole-2-carboxarnide as the bis-triflouroacetate salt (7.1 mg, 15 %). NMR (500 MHz, DMSO-de) delta 8.44 (br s, 1H), 8.22 (br d, J=8.7 Hz, 1H), 8.02 (br s, 1H), 7.93 (br s, 1H), 7.90 – 7.76 (m, 3H), 7.55 (br s, 1H), 7.30 (s, 1H), 6.99 (s, 1H), 6.87 – 6.80 (m, 1H), 5.85 (s, 1H), 3.94 (s, 3H), 2.01 – 1.93 (m, 2H). Four protons from sidechain missing, likely due to overlap with suppressed water peak. LC RT: 1.01 min. M/Z=391.1

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

Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13275-42-8, A common heterocyclic compound, 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, molecular formula is C13H9BrN2, 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: Equimolar quantity of 2-(2-bromophenyl)-1H-benzo[d] imidazole (2) and aniline derivatives in 45 ml of 1,4-dioxan was refluxed for 14 hr with continuous stirring at 80. The completion of reaction was checked by TLC. The reaction mixture was kept overnight in a refrigerator. The solvent was evaporated and a gummy solid mass was obtained. The gummy solid was then washed with cold water and recrystallized from ethanol and water (4:6) to obtain the compounds (3a-3h).

The synthetic route of 13275-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Aruna Chandra; Mittal, Nitin; Pathak, Devender; Indian Journal of Heterocyclic Chemistry; vol. 23; 3; (2014); p. 225 – 232;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 62 (METHOD O); 6,6-Dimethyl-2-[6-(l-methyl-lH-imidazol-2-yl)-2,3-dihvdrobenzo[l,41oxazin-4-yll-6,7- dihydro [ 1 ,31 thiazolo [ 5 A-c] p yridin-4( 5H)-one; A mixture of Intermediate 66 (0.050 g, 0.14 mmol), l-methyl-2-bromoimidazole (0.067 g, 0.4 mmol), tetra-n-butylammonium bromide (0.135 g, 0.4 mmol), Na2CO3 (0.045 g, 0.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) and water (1 mL) in TetaF (3 mL) was heated to 1400C under microwave irradiation for 20 minutes. Additional portions of l-methyl-2-bromoimidazole (0.033 g, 0.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) were added, and heating continued for a further 40 minutes. After cooling to r.t., the reaction mixture was concentrated in vacuo, and the residue partitioned between DCM (50 mL) and water (50 mL). The organic fraction was washed with water (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by preparative etaPLC (Method 6) to give the title compound (0.002 g, 4%) as a white solid. deltaeta (CDCl3) 8.18 (IH, d, J 1.9 Hz), 7.33 (IH, dd, J8.5 and J 1.9 Hz), 7.02 (IH, d, J 1.3 Hz), 6.98 (IH, d, J 8.5 Hz), 6.89 (IH, d, J 1.1 Hz), 5.10 (IH, br. s), 4.36-4.29 (2H, m), 4.12-4.04 (2H, m), 3.74 (3H, s), 2.80 (2H, s), 1.32 (6H, s). LCMS (ES+) 396.0 (M+H)+, RT 1.66 minutes (Method I).

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2008/1076; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 616-47-7 as follows. HPLC of Formula: C4H6N2

(Reference Example 9) Synthesis of ethyl 1-methyl-1H-imidazole-2-carboxylate: Triethylamine (3.40 mL, 24.4 mmol) and ethyl chloroformate (2.34 mL, 24.4 mmol) were added to a solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol) in acetonitrile (4.0 mL) at 0C and the reaction liquid was stirred at room temperature for 16 hours. The reaction liquid was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to obtain ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80%) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 1.42 (3H, t, J=7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J=7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m). ESI-MS: m/z= 155 (M+H)+.

According to the analysis of related databases, 616-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toray Industries, Inc.; ARAI Tadamasa; MORITA Yasuhiro; UDAGAWA Shuji; ISEKI Katsuhiko; IZUMIMOTO Naoki; (95 pag.)EP3263565; (2018); 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(3-Chloropropyl)-1H-imidazole

General procedure: 60% NaH (9.6mg, 0.24mmol) was added to a solution of 5a (100mg, 0.24mmol) in dry DMF (10mL) at room temperature. After stirring for 30min, 1-(3-chloropropyl)-1H-imidazole (52mg, 0.36mmol) was added and the mixture was then stirred for 5h at 80C. After cooling, the mixture was poured into cold water (200mL) and extracted with EtOAc (3×50mL). The combined organic phase was washed with brine (3×150mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/ 20 methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 64.4mg (51.0%) 6a as a red solid.

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; Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 589 – 603;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 2-(Trifluoromethyl)-1H-benzo[d]imidazole

The 4-(4-aminopiperidin- 1 -yl)-6-morpholino-2-(2-trifluoromethylbenzimidazol- l-yl)pyrimidine dihydrochloride used as a starting material was prepared as follows :- Under an atmosphere of nitrogen, a mixture of 2-trifluoromethyl- 1 H-benzimidazole(2 g), 2,4-dichloro-6-morpholinopyrimidine (2.79 g), sodium bicarbonate (4 g) and DMA (28 ml) was heated to 110C in a sealed vessel in a microwave oven for 18 hours. The reaction mixture was heated to 140C for 20 hours and to 160C for 48 hours. The solvent was evaporated from the resultant reaction mixture. The residue was partitioned between ethyl acetate and water. The organic solution was washed in turn with water and with a saturated aqueous sodium chloride solution. The organic solution was dried over anhydrous sodium sulphate and evaporated. The resultant product was purified using a Waters ‘Xterra’ preparative reversed-phase column (5 microns silica, 19 mm diameter, 100 mm length) and decreasingly polar mixtures of a 1% solution of ammonium hydroxide (d=0.88) in water and acetonitrile as eluent. There was thus obtained 4-chloro-6-morpholino-2-(2-trifluoromethylbenzimidazol-l-yl)pyrimidine (0.65 e): NMR Spectrum: (DMSOd6) 3.75 (s, 8H), 7.18 (s, IH), 7.5 (t, IH), 7.6 (t, IH), 7.94 (d, IH), 8.12 (d, IH): Mass Spectrum:M+H” 384.

The synthetic route of 312-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32028; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-56-4, 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. 16681-56-4, name is 2-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

20 g (0.136 mmol) of 2-bromo-lH-imidazole and 3.9 g (0.163 mmol) of sodium hydride were dissolved in 500 ml of THF in a round-bottomed flask, and the solution was stirred and refluxed under a nitrogen stream for one hour. Then, 40.5 g (0.217 mmol) of 3-(2-bromoethyl)pyridine was added thereto in a dropwise fashion, and the mixture was stirred and refluxed for 3 hours. When the reaction was complete, sodium hydride remaining therein was quenched by methanol. After separating an organic layer and an aqueous layer, a solvent therein was all removed. Subsequently, a resultant therefrom was treated through column chromatography, obtaining 23 g of an intermediate compound-15 (a yield: 67%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEIL INDUSTRIES INC.; KIM, HYUN JUNG; CHAE, MI YOUNG; LEE, NAM HEON; HUH, DAL HO; KIM, WOOK; KIM, YOUN HWAN; KIM, JUN SEOK; LEE, SANG IL; LEE, HYUN GYU; JANG, CHUN KEUN; JUNG, JU YEON; (32 pag.)KR2015/66887; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem