Month: August 2021

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-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.

Example 7: (3-(4-1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(1-methyl-1H-imidzol-5-yl)methanolA solution of n-BuLi (2.5 M in hexanes, 0.4 mL, 1 mmol) was added dropwise by syringe to a solution of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (0.500 g, 1.15 mmol, Intermediate 4: step c) in dry THF (13.5 mL) in a dry ice-acetone bath. After 1-2 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (141.6 mg, 1.286 mmol) in dry THF (0.2 mL) was added dropwise. The reaction was stirred for 5 minutes and moved to an ice bath for 1.5 hours before allowing the reaction to warm to room temperature. The reaction was quenched with saturated aqueous ammonium chloride. The mixture was partitioned between water and dichloromethane. The separated aqueous phase was further extracted with dichloromethane. The combined organic phase was dried (Na2SO4), filtered, and concentrated. Crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM), followed by reverse-phase chromatography (acetonitriIe H2O + 0.05% TFA). Product fractions were basified with saturated aqueous sodium bicarbonate and extracted with DCM, before being dried (Na2SO4), filtered, and concentrated to provide the title compound. 1H NMR (400 MHz, CD3OD) delta ppm 8.43 (s, 1H), 8.12 (d, J = 2.4 Hz, 1H), 7.96 (dd, J = 8.7, 3.8 Hz, 1H), 7.83 (dd, J = 8.7, 1.6 Hz, 1H), 7.66 (dd, J = 9.6, 2.2 Hz, 1H), 7.62 (d, J = 8.8 Hz, 3H), 7.30 (dd, J = 12.9, 6.5 Hz, 2H), 6.56 (s, 1H), 6.48 (t, J = 2.1 Hz, 1H), 6.14 (s, I H), 4.57 (d. J = 6.1 Hz, 2H), 3.69 (s, 3H); MS m/e 464.1 [M+H]+

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi, A.; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; WO2015/57206; (2015); 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Imidazole-4,5-dicarboxylic acid

In H2O (12ml) solvent, was added CuCl (0.841g, 0.85mmol), 2,2′-bipyridine (0.086g, 0.5mmol), 4,5-imidazole acid (0.078g, 0.5mmol), NaOH (0.020 g, 0.5mmol), placed on a magnetic stirrer was stirred for 30 minutes, the reaction was placed in 25ml teflon-lined autoclave, sealed in a high temperature oven, constant-temperature 160 C for five days to 5 C / h rate down to room temperature, a blue precipitate in the reactor bulk crystal, in 60% yield (based on copper).

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; Capital Normal University; Lu, Xiaoming; Cheng, Yifeng; (14 pag.)CN103965224; (2016); B;,
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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

First, 4-imidazole formaldehyde (1a, 960 mg, 10 mmol) was added to the reaction flask.Place in an ice water bath. After 10 min, triethylamine (TEA) (278 mul, 2.0 mmol) was added to the reaction flask, and the mixture was stirred in the ice water bath for 5 min.Di-tert-butyl dicarbonate (2.4 g, 1.0 mmol) was then added to the reaction flask, and the reaction was moved to room temperature to react overnight.After the reaction was detected to be complete by TLC, the solvent was spin-dried and alumina column chromatography (PE: EA = 2: 1) was used to obtain intermediate 1b.

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 3034-50-2.

Reference:
Patent; Xihua University; Yang Lingling; Wang Zhouyu; Qian Shan; Li Ling; Xu Wei; Yang Huan; Liu Siyan; Yao Hao; Yan Jie; Li Chao; (21 pag.)CN110294713; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-42-2,Some common heterocyclic compound, 3034-42-2, name is 1-Methyl-5-nitroimidazole, molecular formula is C4H5N3O2, 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 compound 1(2.9 g, 22.83 mmol) in THF (35 mL) was added LiHMDS (1.0 M THF solution, 24 mL, 24 mmol) at -40 C under argon. The mixture was stirred at -40 C for 15 minutes.The aldehyde was added slowly with inner temperature kept below -30 C. The mixture was stirred at – 40 C for 75 minutes before quenched with aqueous saturated NH4C1 solution (10 mL).The reaction mixture was extracted with EtOAc (40 mL x 3), washed with brine (50 mL), dried over Na2504.The solvents were removed under reduced pressure and the residue was purified via flash column to afford clear oil (1.5 g, yield 33%).1HNJIVIR (CDC13, 400 IVIHz) : 7.97 ( s, 1H), 4.22 (m, 1H), 4.00 (s, 3H), 2.24-2.14 (m, 1H), 1.06 (d, J = 6.4 Hz, 3H), 0.93 (dd, J = 1.2, 6.4 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-5-nitroimidazole, its application will become more common.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; MATTEUCCI, Mark; CAI, Xiaohong; CAO, Yeyu; JIAO, Hailong; MA, Jing Yuan; DUAN, Jian-Xin; (52 pag.)WO2016/210175; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 84946-20-3, These common heterocyclic compound, 84946-20-3, name is 2-Chloro-1-(4-fluorobenzyl)-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.

EXAMPLE 42 To a 25 mL 3-neck flask equipped with a thermometer, reflux consenser and stir bar were added, under a nitrogen atmosphere, 885.6 mg (4.8 mmol) of Compound XXII, obtained according to the procedure of Example 41, and 0.93 mL (8.0 mmol) of lutidine. The mixture was heated to 120 C., whereupon a solution of 1.04 g (4 mmol., 1 eq.) of Compound X (Aldrich Chemical Co., Milwaukee, Wis.), 8 mmol of tetrabutylammonium fluoride (obtained from its 1.0M THF solution by distillation under vacuum with anhydrous toluene) and 4 mL of N-methylpyrrolidinone was added slowly over 2 h. The reaction mixture was allowed to stir at 120 C. for 1 h. High-performance liquid chromatography revealed >95% coversion to Compound XXIII. The reaction mixture was allowed to cool to ambient temperature, and slowly poured into a solution of 5% aqueous NaOH while stirring. The resulting suspension was allowed to stir at 0-10 C. for 30 minutes, and the resulting solid product was collected by vacuum filtration, washed with water (3*5 mL), and air dried for 30 minutes under vacuum to afford crude Compound XXIII: 1 H NMR (300 MHz, CDCl3) delta7.52 (1H, d, J=7.8 Hz), 7.20-7.00 (7H, m, two groups), 5.13 (2H, s), 4.40 (1H, NH br. d), 4.32 (2H, pseudo d), 4.20 (1H, m), 3.00 (2H, pseudo t), 2.15 (2H, pseudo d), 1.30 (2H, m overlapped), 1.26 (9H, s); 13 C NMR (75 MHz, CDCl3) delta176.3, 164.2 and 161.0 (13 C-19 F coupling), 153.3, 142.4, 134.6, 131.4, 128.4, 121.7, 120.0, 116.6, 116.4, 116.1, 107.5, 50.5, 45.1, 44.2, 38.9, 33.1, 28.6. It is to be noted that under the same reaction conditions as above, but without the use of tetrabutylammonium fluoride, only 3.5% conversion (high-performance liquid chromatography) to Compound XXIII was achieved after 3 h at 120 C. The Compound XXIII obtained above was placed in a 50 mL, 3-neck flask equipped with a thermometer, reflux condenser and stir bar. 5 mL of 48% hydrobromic acid was added, and the resulting mixture was heated to 110 C. and allowed to stir at that temperature for 2 h. After the reaction was complete (>98% conversion to norastemizole as shown by high-performance liquid chromatography), the reaction mixture was allowed to cool to room temperature, and 10 mL of toluene and 10 mL of water were added, with stirring.

The synthetic route of 84946-20-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sepracor Inc.; US5817823; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1,Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

1-Methyl-4-imidazolecarboxylic acid (4-1) (265 mg, 2.1 mmol)Was dissolved with N, N-dimethylformamide (12 mL)N-Methylmorpholine (850 mg, 8.4 mmol) was added with stirring,The reaction solution was placed in an ice water bath and slowly stirred for 10 minutes,Trimethylacetyl chloride (277 mg, 2.3 mmol) was then slowly added dropwise,Complete addition the reaction was stirred for 30 minutes under ice-water bath maintained;After the anhydride is completely formed,Under ice-cooling, a solution of 1- (4-methoxyphenyl) -3-methyl-2-piperazinone hydrochloride (4 -2) (462 mg, 1.8 mmol)Plus,The reaction was stirred at room temperature for 1 hour, followed by monitoring the reaction; After the reaction was completed, quenched with water, the reaction was concentrated in vacuo, the concentrate was extracted with dichloromethane, and then washed with saturated brine, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure.The concentrate was subjected to column chromatography to obtain a white solid1- (4-methoxyphenyl) -3-methyl-4- (1-methyl- 4- carbonylimidazole) piperazin- 2-one (compound- 4),Yield 70percent,

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujian Jinle Pharmaceutical Technology Co., Ltd.; Zhou Zhongxiang; Xing Yuanyuan; Chen Yingzhong; Deng Chengjun; Deng Honggui; Xue Wanhua; Zhang Shuzu; Chen Weipeng; Li Fang; (27 pag.)CN107174584; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 71759-89-2, These common heterocyclic compound, 71759-89-2, name is 5-Iodo-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.

Step 1 To a solution of 113a (Synthonix, 5.0 g, 25.8 mmol) in THF (100 mL) at 0C is added portion wise NaH (60% in oil, 1.13 g, 28.3 mmol). The reaction is warmed to RT for 30 min and then cooled to 0C. EtBr is added and the reaction is stirred for 1 h at 0C, and then warmed to RT. The reaction is diluted ammonium chloride (10 mL) and NaHC03 (saturated) is added. The aqueous phase is extracted with EtOAc (100 mL). The organic layer is washed with water (2 x 20 mL), brine, dried (MgS04), filtered and concentrated under reduced pressure. Purification by chromatography (40-100% EtOAc/Hexanes) affords imidazole 113b.

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STURINO, Claudio; BEAULIEU, Pierre; DEROY, Patrick; DUPLESSIS, Martin; JAMES, Clint; LACOSTE, Jean-Eric; MINVILLE, Joannie; MORENCY, Louis; MORIN, Sebastien; SIMONEAU, Bruno; TREMBLAY, Martin; WO2013/91096; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

Step 1. 4-Iodo-l-methyl-lH-imidazole and 5-iodo-l-methyl-lH-imidazole (1205) [00394] Under an atmosphere of nitrogen at 0 C, a solution of 4-iodo-lH-imidazole (5.82 g, 30.00 mmol) in THF (50 mL) was treated with portionwise addition of sodium hydride (60% dispersion in mineral oil, 1.44 g, 36.00 mmol). After stirring for 30 min at 0 C, iodomethane was added (2.8 mL, 45.00 mmol) and the mixture was stirred for 1 h at 0 C. The reaction mixture was poured into water (100 mL) and was extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 6.24 g (90%) of a -3 : 1 mixture of 4-iodo-l-methyl-lH-imidazole and 5- iodo-1 -methyl- lH-imidazole as a light yellow solid. MS (ESI) m/z 209 [M+H]+.

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, 5-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); 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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4ClN3O2

Methanamine (2M in THF, 15 mL) was added to a sealable tube containing 2-chloro-5-nitro- 1 H-benzo[d]imidazole (1 g). The reaction flask was sealed and stirred at 80 C for 16 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was washed with diethyl ether (15 mL) and dried in vacuo to afford the crude title product as a black tar (600 mg), which was used directly without purification. LCMS m/z 193.06 (M+H)+.

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 5955-72-6.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); 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. 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, A new synthetic method of this compound is introduced below., Recommanded Product: 360-97-4

(c) 4-f(2-Meth.yl-2-propoxypropyl)amino]–lH-imidazole-5-carboxamide; The reaction mixture of 2-methyl-2-propoxypropanal, which was obtained from Example 2(b), (1.0 g, 8.3 mmol), 5-amino-4-irnidazolecarboxamide (0.5 g, 4.0 mmol), sodium cyanoborohydride (0.25 g, 4.0 mmol) and acetic acid (0.45 mL, 7.9 mmol) in 10 mL of methanol was stirred at ambient temperature for 1 h. The solvent was removed in vacuo. Water (20 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the solvent was removed in vacuo. Purification by ISCO flash (EtOAc:Heptane, gradient elution 1:1 to 100% EtOAc) gave 0.19 g (20 %) of the title compound. 1R NMR (CDCl3) delta ppm 6.98 (s, IH), 6.39 (br s, IH), 3.40 (t, 2H, J=6.7 Hz), 3.14 (d, 2H, J=4.3 Hz), 1.56-1.65 (m, 2H), 1.22 (s, 6H), 0.95 (t, 3H, J=7.5 Hz); MS (ESI) m/z 241 (M+l).

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; ASTRAZENECA AB; WO2007/142576; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem